John Gauch 2025-08-03 John Gauch 2025-08-03

Struggling with Growth? You Can't Create Demand—You Need to Find It

If your emails, ads, or other sales and marketing activities are falling flat, it might be that you’re trying to generate demand where none exists. In this post, I break down what’s at the root of PMF and growth by reviewing the basics: uncovering real problems felt by people actively trying to make progress.

Illustration created with the assistance of ChatGPT by OpenAI.

Hi! I'm a startup fractional COO who works hip to hip with founders as their operating partner. I amplify founder contributions by serving as a thought partner and taking on critical and delegable growth and operations responsibilities, particularly for companies in the $1 to $10 million revenue range. Over 20+ years, I have worked on dozens of startups (Synervoz, Feldspar, Axiom, Spartan, IAN), helping build one industry-transforming business to exceed $100M in revenue and a second to (so far) nearly reach that very rare milestone.

Introduction

You've noticed that your emails aren't hitting. Or it's your ads. Or it’s your trade show booth meetings. Are your prospects numb? Is it the ICP? The channel? The messaging? Maybe AI is steering you wrong, or it’s just the times.

You're not alone.

If you’re the founder of a venture-backed startup, you’re rightfully preoccupied with the idea of finding product market fit (PMF). If you’re the founder of a profitable business with similar growth ambitions, you’re also looking for an unmet or undermet problem you can solve to increase sales.

It’s hard.

So, what will it take to grow your business? First and foremost, it will take getting the basics right.

You Can’t Manufacture Demand

To start, let's get on the same page with one fundamental idea: You can't manufacture demand for your product where it doesn't exist. You can only discover prospects by identifying the people who are already feeling friction in their lives and are trying to make progress.

If people don’t have a problem to solve, or there aren’t enough of them to meet your business’s requirements, there’s never going to be scalable PMF. There’s never going to be a promising new growth channel.

I won’t get into it here, but your solution also has to outperform the alternatives—not across the board, but at solving that specific problem, for that specific person, in that specific moment. It doesn’t have to be perfect. It doesn’t even have to be great. It just has to be better than their current solution or workaround—or better than doing nothing.

Sales and marketing is about finding and connecting with people who are struggling with a problem and searching for a solution. They might not know precisely what they need at the start, but if your solution clearly helps them achieve a better future, you have a chance to be the one who helps them. Your most promising short-term prospects aren't the passive lookers either. It is the group of people actively looking and deciding how to solve their problem.

Some people may be stewing with their problem and not taking any action besides feeling unhappy. “Silently suffering” is how someone put it once. They're too early in the buying timeline to become a customer today. You want to connect with these people, too, and consider ways to nudge them along (more on that below). Initially, focus on prospects further along in the timeline.

Here's an example of what I mean: Say you build and license an audio SDK. Your potential market today consists of developers who are currently facing an audio challenge that your product solves. It's not every developer who is part of a team building audio tech.

No problem, no customer.

This framing draws on the Jobs to Be Done framework, co-developed by Bob Moesta.

Use the Four Forces

Bob also describes how four forces drive or resist the change entailed in buying something new:

Pushes (away from current pains)
Pulls (toward an exciting new solution)
Habits (comfort in what is familiar)
Anxieties (fear of what change means)

Purchases occur when the pushes and pulls are strong enough to overcome the friction of habits and anxieties.

Effective sales and marketing encourage a shift from the old way to the new way by strengthening the forces promoting change and reducing those causing drag. When you get that right, as Bob Moesta says, people pull your product into their lives.

Let's walk through two foundational and durable sales and marketing concepts that follow from these principles:

Read also: How to Learn Jobs to be Done

Provide Value

We said the purpose of a business is to help people make the progress they desire in their lives. It's not just a product obligation; that should be the mission of the organization as a whole. The entire customer experience should be designed with this end in mind, including sales and marketing.

Sales and marketing shouldn't push your product. Effective Sales and marketing helps people clarify their problems and shows them how to take the next steps to solve them. It’s a big, scary world out there, sales and marketers ought to see themselves as guides helping prospects choose a path to a solution. Engaging with customers like this also earns trust from genuinely being helpful.

That's delivering value.

Imagine how a prospective customer can move from where they are to where they want to be. This approach to sales and marketing centers on questions like:

How are people feeling now, in their struggling situation? What are people trying to do but can't? What's frustrating them?
What does better look like? How does your product help? What are its strengths and shortcomings?
To make a switch, from where someone is now, what do they need to know? What gets in their way? What are they afraid of? How do you tap into what motivates them and reduce their fears and anxieties?

Again, your go-to-market motion must make the math of the four forces work (pushes + pulls > habits + anxieties). No product bragging. No "educational content" that doesn't have a clear purpose. Foster self-motivation that helps someone move forward.

How does your sales and marketing stack up?

Show Up at Watering Holes

To apply this sales and marketing principle, you need to find people in a struggling situation. Go where they already are or find a way to bring them to you.

This isn't easy, but it's critical.

Look for the places and ways your audience has “opted in" to being a prospect. That's where you need to be, too.

Let me give you a concrete example. One particularly well-performing cold outbound campaign I worked on started by scraping public information about attendees at a niche audio industry event:

By attending that event, people raised their hands to say they were working on and cared about the kind of audio projects we care about, demonstrated by our audio SDK and related services.
We crafted an outbound email that linked to a YouTube talk on a timely, thorny audio challenge by one of our team members who also attended the event. The talk was technical and useful; it was not a sales pitch. Many event attendees may have been wrestling with or would be curious about the subject matter.

The campaign emails had a 55% open rate, a 30% click-through rate, and an 18% reply rate. It also converted a new customer immediately and opened up conversations with several others.

Why did we achieve those results?

We'd zeroed in on a much more promising audience than "every developer on a team building an audio product or feature." Still, not everyone who got our email was a potential customer. But by attending the event, they'd raised their hand to say they wanted to learn something new. Many were likely trying to connect the dots to understand or solve an audio challenge.

We distinguished ourselves by demonstrating our expertise as audio problem solvers. Even if we didn't address the exact problem someone was working on, the talk topic was curiosity-arousing, and it doesn't take a massive leap for a watcher to bet that if we could help with one audio challenge, we could help with others like it.

Are you showing up when your most likely customers come knocking?

Organic SEO is often underutilized by entrepreneurs because it requires a bit of time to yield results. It's sidelined in favor of performance marketing or cold outbounds perhaps. But organic SEO is how you get discovered by people actively searching for solutions to a problem. This is huge. These people have intent. They're already looking for you. You don't need to chase them; you just need to be easy to find.

And this is more important now than ever.

It's not just people searching. It's AI agents.

The same general principles that help you rank in Google will help you get pulled into AI-generated suggestions, too. Stick with the fundamentals: In the simplest terms, create genuinely helpful content, keep it updated, and keep at it.

Where are the watering holes your prospects are hanging out right now?

Example: From My Business

As a fractional COO, I work with founders who have already achieved considerable success with their companies, closing a Seed or Series A financing and generating $1 million to $10 million in annual revenue. Many of them are in tech, but not all. Some are venture-backed and others are profitable growth businesses.

However, not every founder meeting that fits that description is a real prospect.

My prospects are unhappy with how their business is going:

Finding scalable PMF after early traction might be proving difficult.
Growth may not be where they want it.
They may be feeling the team isn't aligned or executing well.
Business operations may be creaking, groaning, or breaking altogether.

They want to see giant leaps forward, as well, not incremental improvements.

They're likely overworked and stressed, as a result, which leaves them emotionally and physically frayed, from doing too much. Still, they’re fighters, with big ambitions. It’s not just about money either. Many aspire to transform the very nature of the industries in which they operate.

These founders we feeling a lot of pressure.

Again, I don't serve every founder fitting the high-level demographic criteria I shared (e.g., someone running a $1 to $10M business). They need to be in a struggling situation, similar to what I shared.

They’re not my prospective customer if:

They have the support they need, and it’s going well.
They lack the support they need, you don’t want to do anything about it, and they’re okay with the implications.

The people I help are unhappy (and likely aware of it) with their current situation, and they're either passively or actively exploring how to solve for it. They are on the buying timeline somewhere between their "first thought” and deciding on a purchase.

How did they get into that situation? When the company grows, founders need to grow too. They need to adapt their role. Too often, they try to do it all in the face of increasing challenges, such as:

finding PMF or a new growth lever amid growing operational demands, or
orchestrating and managing their scaleup if they've tapped into growth

The founder role needs to change, and they may require an operating partner to make that happen—someone to take on mission-critical but delegable tasks, allowing them to focus on the top two to three things that only they can do, as CEO and founder.

My prospects are dissatisfied and want to make changes. When the math of the four forces works out, they work with me or implement another solution to make progress. The role of my go-to-market activities is to help founders figure out what they need and how to choose the right solution to achieve their personal and business goals.

To illustrate, as part of my content marketing efforts, I wrote a LinkedIn post that discusses how founders can become stuck trying to do it all in their businesses, why this is an undesirable situation, and how to start getting out of it.

I've connected with founders where they are, on LinkedIn.

I've specified who I want to speak to by asking if they feel they may be a bottleneck to their business.
For those who feel this way, I hope I've helped them understand why this might be happening.
And I’ve suggested ways to get out of the situation—i.e., baby steps on the buying timeline toward making a switch from what they are doing now.

The LinkedIn post isn't about me; it's about the founder. However, it’s doing the important work of helping the founder and creating a potential future customer.

Conclusion

The take-away: Treat sales and marketing as a genuine effort to help someone solve a meaningful problem in their lives and turn that demand into a purchase.

You can't create demand. But you can spot it, understand it, and work with it. If your sales and marketing efforts help someone in a struggling situation make sense of what they're facing and take one step forward, that's a win. And that's how you grow, by putting one step in front of the other.

Want help applying these ideas to your business? Reach out or follow my contributions on LinkedIn.

John Gauch 2025-07-31 John Gauch 2025-07-31

Journey of a Founder: Series B to Series C—Scaling Challenges and Leadership Imperatives

Every startup that reaches Series B has proven something, but sustaining growth, scaling teams, and building durable systems is a whole new test. What changes at this stage, and how do founders evolve to meet it? In this founder/operator roundtable, we dive into the next phase of the journey: from Series B to Series C. We cover what shifts in mindset, systems, and leadership.

Event 1—Part 1: Hosted by John Gauch and Jimmy Malik.

Illustration showing startup event title and participants John Gauch Jimmy Malik Alice Nawfal and Justin Etkin for part 2 blog post

Hi there - I'm a startup fractional COO who works hip to hip with founders as their operating partner. I amplify founder contributions by serving as a thought partner and assuming critical and delegable growth and operations responsibilities, particularly for companies in the $1 to $10 million revenue range. Over 20+ years, I have worked on dozens of startups (Synervoz, Feldspar, Axiom, Spartan, IAN), helping build one industry-transforming business to exceed $100M in revenue and a second to (so far) nearly reach that very rare milestone.

In case you missed my first blog post on the messy middle between Series A and B, in this follow-up, we zoom in on what it takes to survive and scale between Series B and C, when expectations shift, systems strain, and leadership is under the microscope.

Jimmy Malik and I hosted this second roundtable in our Journey of a Founder series in collaboration with the Operators Guild (OG), where we're both members. Our guest co-founders (and fellow OGers) were Alice Nawful, of Notabene, and Justin Etkin, of Tropic.

I summarize the top insights for you here.

We don't cover everything, but we cover a lot. Enjoy.

Introduction

Scaling a startup from Series A to Series C is full of tough choices, shifting priorities, and relentless tests of leadership. What worked at Series A can fall apart at Series B or later in the face of increasing demands for growth, structure, and disciplined execution.

This post breaks down what it feels like, critical areas to focus on, and lessons every operator can apply. These insights aren't just for venture-backed companies either; they're relevant if you're the founder of a growing business that needs to evolve from scrappy, founder-led leadership to making major leaps in performance.

(This is Part 2. If you missed Part 1 on Series A → B, read it here.)

What Series B to Series C Feels Like

Series B is another test, a different kind of proving ground. The scrappiness that got your startup from zero to Series A, or your high-growth business to substantial annual revenue, is no longer enough.

You're not proving the business can work anymore; you're proving it can scale and operate reliably and efficiently without running off the rails. You need to do this with rigor without sacrificing speed. The stakes rise as customer numbers and expectations increase and the number of team members swells. If you have a Board of Directors or investors, they're demanding proof you're on top of things at a whole different level.

This isn't easy, in large part because the practices, habits, and ways of working that served the company so well through Series A may be becoming liabilities at Series B, which can feel disorienting. Being creative and scrappy isn't always enough anymore. Sustainable process-building feels different.

Leadership issues and people management are more stressful than ever. Delegating significant responsibilities to new leaders is an emotional test. Unnerving. Functional leaders are popping up and (hopefully) stepping up. Trusting and supporting new leaders while holding them to high standards is a delicate balance. Meanwhile, existing and new team members may be nursing bruised egos if they were passed over for a new senior role or managed, or they don’t get the exact title they were expecting.

For the first time, company operations take center stage, and ops is in the hot seat. Can they handle increasing complexity, rising expectations, and higher volume? Operational issues can snowball into an avalanche. Some teams are entering the Series B phase with weak systems that need upgrading. Others arrive with no real systems at all, having punted on operational investments after Series A. For the latter, it can be a brutal awakening.

Unexpected challenges arise at this stage, too. It could be growth concerns, team misalignment, or broken systems. Things that can create friction or stall progress. The issues may be different from Series A, but they are just as critical to overcome.

Finally, resource management is still in sharp focus. It's not just about growth. More parts of the business demand investment. So you need to decide what to invest in and when across the company to optimize revenue and keep the business humming. You can't succeed on the growth front if the rest of the system seizes.

Top Imperatives

Series B demands a shift: from chasing growth at all costs to building repeatable, sustainable growth that can scale without breaking the business. Companies can't simply continue doing what worked before; they must evolve their DNA to meet new demands. Embrace this reality.
Be deliberate about who belongs at the decision-making table with the CEO and COO. Your operational rhythm, how your team communicates, aligns (or not), and executes, will be tested hard. Scrutinize it for fractures. Line up the functions and teams behind this group.
Understand that you're building complete functions now. Structure and build a world-class team from the existing bench and new hires, believing in people, but not overbelieving, and drawing in newcomers who help, not hurt. You may need to correct Series A missteps. Some of your early stars may struggle in this new version of the company. They haven't failed, but needs have changed.

As founder and CEO, you've been out of the weeds for a while by now. Your COO has also begun to pivot in their role, and this will continue. They need to be more focused on prioritization, alignment, and accountability. They're no longer the single source of truth or the person closest to every operational detail.

Layers of leadership and cross-functional dependencies can create bottlenecks. You need to deliberately balance speed with alignment. Too much time spent on getting alignment, and decisions stall; too little, and the organization fails to make progress on what it’s decided.

Just as you were in the prior period, be honest about who fits in, and make the tough calls when they don't (with care and consideration). Putting the wrong people into the wrong roles may not cost you the business at this point, but it will come at a cost.

Triage broken processes and then revamp, rebuild, or build. Did you invest, soon enough, after your Series A, in critical systems you need now? Series B is when cracks stop being theoretical and start costing you real time and money. Avoid crashing out completely. Remember you're building for today and tomorrow.
Lean into data-informed decisions, but don't lose your agile instincts. The new systems and processes you're implementing are generating a vast amount of data. You need that to get your arms around what's happening with a business of this size, but don't let it drag you down; remember that you still need to be moving quickly.

Finally, be prepared for Board expectations shift from a grand narrative delivered by the founder to hard metrics during this period. You can't just tell the story anymore. You have to show measurable, data-backed results. The Board will be looking more carefully than ever at those gorgeous financials prepared by your first, top-notch VP of Finance. Resource decisions are about growth and efficiency now. Can you show that you are scaling without overspending?

If you're strategizing your next phase of growth at your founder-led business, I'd love to discuss your plans.

Read Part 1: Series A Is a Reckoning: Operator Imperatives for Getting to Series B

John Gauch 2025-07-30 John Gauch 2025-07-30

Journey of a Founder: Series A Is a Reckoning—Operator Imperatives for Getting to Series B

The Journey of a Founder series continues. You’ve raised a Series A. You’ve got early traction and capital to grow. But now the real work begins. What does it feel like to lead a company through this phase, and what actually helps you reach Series B? In this founder/operator roundtable, we explore what happens after the early wins, from hiring and trust-building to evolving your founder role and avoiding the ops pitfalls that can sink momentum. This is the messy middle, what I sometimes call “the reckoning.”

Event 1—Part 1: Hosted by John Gauch and Jimmy Malik.

Illustration showing startup event title and participants John Gauch Jimmy Malik Alice Nawfal and Justin Etkin for part 1 blog post

The roundtable video recording isn't available publicly; however, I have summarized some of the top insights for you here. I also recommend checking out the OG if you're a company founder, co-founder, or operator at a high-growth business looking for a like-minded community of peers.

We don't cover everything you need to know to run a business, but we cover a lot of ground. Enjoy.

Introduction

Scaling a startup from Series A to Series C is full of tough choices, shifting priorities, and relentless tests of leadership. What worked at Series A can fall apart at Series B, or later, in the face of increasing demands for growth, structure, and disciplined execution.

(This is Part 1. If you're looking for Part 2 on Series B → C, read it here.)

What Series A to Series B Feels Like

You've shown notable progress with the business. However, it's not yet clear you're on a reliably upward trajectory. There's going to be a lot more fight before you can declare victory (or defeat). Founder-financed companies often find themselves in a similar spot after they've proven their business works when there's potential and the path forward isn't obvious.

I see this period as a reckoning.

The basics that got you here still matter: understanding customers, testing assumptions, making thoughtful decisions, hiring smartly. Capital in the bank doesn't change that; if anything, it raises the bar. What are you going to do with that money?

At the same time, the work itself shifts. The breadth of problems, the pace of decisions, and the complexity of the business all spike. One hour, you're deep in the weeds fixing a broken operational process; the next, you're selling a senior leader you want to hire on your vision. This context switching is relentless. And because the data you wish you had doesn't exist yet, you need to rely on gut feel over hard knowledge more than you like.

This stage also brings a psychological shift: Trust becomes an increasingly valuable currency. The only way you, the founder, can share the management burden with teammates is if you have trust in them and the way you work together. To reach this point, a high-performing company has likely tapped an operating partner to the CEO, allowing the CEO to promote the company vision and focus on strategy and top initiatives only they can lead. If this hasn't happened yet, and you want the business to continue to move forward in leaps and bounds, it's time.

Likely, you're gearing up to hire for other roles, too. In addition to filling staff roles to keep up with growth, you may be bringing on more experienced people who know more than you do in their area of expertise. That's the point. But it can still feel jarring when you're ready to make your first full-time finance hire, for instance, and you realize how much more they know than you do. It's humbling.

Meanwhile, your operational foundation gets stress-tested: finance, legal, HR, and other business ops. Building operations to date has been iterative, making trade-offs and putting together "good enough" processes to serve your current and near-term future needs. Systems or processes you justifiably deprioritized before might cost you time, money, and goodwill now. You may need to revamp what you had prioritized and put into place earlier, and quickly catch up on things you ignored or hacked together … or risk dragging down the business.

In this period, as well, unexpected and hairy challenges lurk. Every company has its version. The business is not entirely settled. You're confronting unknowns as well as potentially disruptive events in the external environment, like a shift in market demand. There's always something material still to figure out.

Was product‑market fit (PMF) real or a fleeting bump?

Is the market big enough to support your scale objectives, or you we about to hit a wall?
Are you ready for the larger customers and new segments you’re chasing?

One thing that's not unique to this period is the careful decision-making required around how to use your resources: Remember that cash in the bank? For a venture-backed concern, this is your latest round. For a high-growth business, it's your accumulated war chest. You'll need to make deliberate decisions between extending runway, investing in critical infrastructure, and accelerating growth.

Series A is about continuing to refine the business and building certainty while everything—your business model, your market, your product, your processes, your team, and you—is being stress‑tested. It's exciting. It's demanding. It's a trial that you need to survive to build and sustain a successful business that has a big impact on the world.

Read also: Journey of a Founder: A Startup Story

Top Imperatives

Remain customer-focused and dialed into the problem you solve for them. Stay curious. Treat PMF as a moving target. There may be a difference between the early signs of PMF (what gets you to a Series A) and the durable, scalable PMF you need to reach Series B and beyond.
Shift your time, as founder, from the early days, when you did it all. Ideally, you did that before now. Less time in the weeds, more big-picture leadership. You can't solve every problem.

As the founder, you need to reduce your information advantage by spreading what you know among the team. (It can feel scary.) The quality of your operational rhythm dictates how comfortable you may be staying out of the weeds. Bi-directional processes giving all parties the information they need will tell the founder where the team is headed. If that's the right direction, you'll be able to focus confidently on your uniue founder’s agenda. Low trust resulting from poor hires or operational deficiencies is often what leads to micromanagement. When this is all working perfectly, it can still feel stressful, since you aren't as close to the details of the business anymore.

Accept that your team is in a period of flux. You still need standout generalists, and you're also bringing on subject matter experts and possibly introducing different levels of seniority. It's going to get a bit messy. Don't let your ego get in the way of hiring people who outclass you. Be careful: It's tempting to over-title early hires or promote generalists too quickly.

The company may be transforming itself every six months. Don't let your leadership approach or the team fall behind. Pick a frequency (quarterly, for example) and conduct a holistic check-in on the current business needs and how you and your team is aligned.

What's working well?
What's not working?
What's missing?
Who can step in or step it up?
How do you fill the gaps?

Suppose someone isn’t scaling to match business needs. They may need additional support, or if the situation can’t be improved, you may need to n that case, acting sooner may feel uncomfortable than later, but it may be the right move.

Prioritize like your life depends on it. The team can't do everything that needs to be done either. Be explicit about what matters most right now. Consciously pick what you're going to knock out of the park, what's going to get midling attention, and what's less important. Be explicit about it. Decide how to sequence initiatives.
Keep ops lightweight but strong enough not to break. The startup debt that hurts the most isn't always engineering. It may be in finance, customer success, or another area. Stay alert. Invest in the key areas. Expect many of the ways you do things now will break, and you'll need to patch them up or replace them later.

Finally, avoid this misstep: Growth is the ultimate imperative, but so is avoiding an existential crisis originating from the failure of the company's operations. Ask yourself: What do we need to be working on today that might not have an immediate impact but will be critical soon? Some improvements have long lead times. Plan the rebuild before events make change a crisis or impossible.

If you're in this stretch of business building (i.e., wrestling with growth, hiring, patchingor rewiting operations), I'm always up for a conversation.

Read Part 2: Series B to Series C—Scaling Challenges and Leadership Imperatives

John Gauch 2025-03-23 John Gauch 2025-03-23

Journey of a Founder: A Startup Story

Every startup faces pivotal moments—turning an idea into a product, finding early customers, securing funding, and scaling successfully. But what challenges arise at each stage, and how do you navigate them? Check out a recording or transcript of our roundtable with two experienced founders. This is an online event where we break down the founder’s journey from Inception to Series A—exploring key milestones, common challenges, and actionable strategies to move forward.

Event 1: Hosted by: John Gauch and Jimmy Malik.

Welcome - I’m a hands-on startup fractional COO. I serve as an operating partner to founders supporting growth and operations. Over 20+ years, I have worked on dozens of startups (Synervoz, FreshAhead, Axiom, Spartan, IAN), helping build one high-impact business to exceed $100M in revenue and a second to (so far) nearly reach that rare milestone.

Introduction

A founder roundtable on scaling from inception through Series A

In this live discussion that I co-hosted with fellow operator Jimmy Malik alongside founders David Zamarin (Detrapel) and Zak Allen (Flyhomes, Hearth), we explore the real challenges of building a startup. We cover validating your product, raising seed capital, building early teams, achieving product market fit, and sustaining momentum into Series A, with candid founder stories, lessons learned, and tactical advice you can apply right away.

This is a lightly edited transcript from our roundtable, a live startup event.

(This is the first in a two-event series. To learn about scaling from Series A to B and from Series B to C and beyond, see this event recap.)

The timestamps in the transcript synchronize with this edited audio of the event.

John: [00:00:00] Let's get started with some intros. Beginning with myself, I'm John Gauch, a five-year startup fractional COO for companies like Feldspar, FreshAhead, and Synervoz. I'm an occasional sales coach and mentor. Over 20+ years, I've applied my growth and operation skills to help dozens of startups like Axiom in the legal space and Spartan in consumer. I started my career as a tech lawyer in New York City. I developed myself in business roles after that. So far I've been lucky enough to help build one high-impact startup to nearly a hundred million dollars in revenue and a second to exceed that mark. I love serving founders through my work and I'm excited to be here. With that, I want to turn things over to Jimmy.

Jimmy: Great. Thanks, John. Hey, everyone. Jimmy Malik. I'm an operational strategist and growth leader, so I specialize in helping founders develop and implement operational strategies to drive scalability and sustainable growth. [00:01:00] I've worked across multiple industries, government, finance, healthcare, technology. I work with startups now to streamline execution, optimize their resources, navigate the complexities that they face in scaling their organizations. One of the things that I feel drives success across startups is those early hires that help you cement the culture and create an atmosphere that entrusts your values and your mission leading to your scalable execution. I'll turn it over to our founders. Why don't we start with David?

David: Hi, everyone. My name is David Zamarin. I'm the founder and CEO of a company called Detrapel, which is the parent company of three brands, called ProofPlus, Impermea Materials, and Detrapel Solutions. It's a company that I've been running for over 11 years. I started when I was 15 years old and the company has grown quite a bit. [00:02:00] So you'll get to hear a little bit about that. We've been on things like Shark Tank in the past. All the way through scaling up the business and now being a very large industrial company.

Zak: Awesome. I'll go next. Hi everyone. I'm Zak Allen. My background is at the intersection of real estate and software. I was early at Flyhomes and, as well as Hearth, building up those companies from zero all the way through Series B, leading the tech and engineering efforts there. I also co-founded a company called Homemade, and I'm working on a new venture as well. But based in Austin and I love the intersection of the kind of physical built world with the software world as well.

Inception to Seed

Jimmy: All right. Thank you guys. So I'll kick us off here into our actual discussion. And as David mentioned, this is more of a dialogue discussion where we're not gonna—it's not death by PowerPoint or anything like that. We do have a few slides just to help narrate and summarize some of the key points that we're making as well as our founders. [00:03:00] So let's just get into it right.

So, as many of you can probably attest, the beginning of the journey of being a founder is exhilarating, right? The moment when inspiration might strike when you first sketch out your idea, when you share it with someone who gets it. You fast forward a few months, and suddenly, things are starting to fall in place. You've validated the problem, maybe even built out a prototype, and attracted some early believers. And then the big moment. You raise that first, your first round of funding. It feels like a win, which it is. But there's the, here's the thing, right? The funding just isn't the finish line. It's the starting gun. And this is where the real work begins. The shift from, "I have an idea" to "I'm building a company." And that's what you're, that's what we're going to dive into now. What it actually means, between the inception and seed, and how founders navigate the uncertainty of this phase.

So the early days are really more about the excitement of [00:04:00] funding. In this phase, what we call inception to seed is where the foundation is laid, where you start asking and answering some really critical questions, such as have we truly identified a problem worth solving? Are we building the right solution? And does the market opportunity align with the long-term vision?

So this is where you may go from "this could work" to "this is working" or "it's not working." At this stage, there are three core areas. So John and I, working with founders, have distilled this down to three core areas, which we think are really important for this phase: validating the problem and refining the solution. This means getting out there and talking to real users, stress-testing your assumptions, and making sure you're solving something people genuinely need. You're also building an early product, which might be a prototype, an MVP, in some cases, even a well [00:05:00] structured conversation or, excuse me, a well-structured pitch that gets people excited, and you're also figuring out your early business model, right? Can this actually be monetized? Even if this is a need, are people willing to pay for this? Is there real demand? Are there others, competitors, others that have figured out how to do it better?

As you might guess, none of this happens in a straight line. It goes all over the place. You take detours. You may even hit some dead ends, and then you'll have some breakthroughs. All right.

So some of the biggest hurdles that founders face in this stage I would say are validation versus reality. So how do you know you're solving a problem that people will pay for building credibility? Investors, early employees, early customers. How do you get them on board and the first hires? As I was saying, the first hire is you're building a team. There's no company culture yet. So how do you find the right people when your startup is still more, a little more or less still a vision, [00:06:00] right? You don't want to, you don't want to start hiring your friends.

And then, the bridge.

The bridge is what we call what you need to do to get from the initial stage into the next stage. Moving from inception to the actual seed, it's about building momentum, right? Founders who win here lean heavily into their customer discovery. So constantly testing, iterating, and finding a product based on real feedback.

And they show early signs of traction. Whether that's increased user growth, revenue, or just strong engagement, even if it is still scrappy. And they're able to craft a strategic narrative, right? What a compelling story that investors, hires, and customers can rally behind.

And I can't stress this enough: where I've seen founders and startups where they have an amazing idea to solve a critical problem. But they can't tell a good story. So it leaves customers and investors scratching their heads in terms of what is the actual outcome of something like [00:07:00] this.

Now rather than just talking in theory, let's bring in, let's talk to our founders and see what they think. Dave, let's start with you. How do you navigate this phase, and what are some of the biggest hurdles in validating your problem and convincing investors you're onto something here?

Founder Experiences: Building a Customer Trust System

David: So it's a lot harder said than or easier said than done. I think the biggest thing that most investors will look for, whether that's an institutional fund, a CVC or corporate venture capital arm, or an angel investor in the early stage, is primarily they're focused on your team. The second thing they're focused on is whether or not you've found product market fit, and in the earlier stages, it's pretty easy to assume that you have not just yet, and that's okay.

What they're looking for and what you as a founder need to be obsessed with is validating that you've built the right product that will address multiple needs across multiple customers. [00:08:00] And the easiest way to do that is to have an infinite feedback loop with your customers.

As you're building, you have to get rapid prototyping, rapid feedback from your customers in real time, build a product that would solve their needs, then take that to another customer, maybe simultaneously, and see if those needs are identical. And if not, that's okay. See how you can blend those two.

And as you're getting all of this feedback, you're also building a trust system with these customers, who then could also advocate for you when it comes time to do due diligence in your fundraising, and you will be asked for customer attestations.

Those are the typical early-stage things that I think are often said, and most people would say that they're doing that or they have done that.

The truth is that you never have enough because the more people you have who have used or have put feedback into the product will be those early adopters who can speak for you and speak towards the technology and how much they're willing to pay for it [00:09:00] and essentially define the market size for you and for the investors when they're doing their diligence. That's what I would recommend.

Zak: Just to expand on that, that's great foundation, I think in order to get those early adopters, you can't be afraid of launching too early. There's a saying where if you're not embarrassed by the first product that you launched, then you've launched too late.

And in theory, you could be building your lead list, trying to see what the ideal customer is and spending six months just building something. But if you're in, if you're doing that in isolation, then you're not actually proving you're doing anything. You're not actually proving that demand. You need to launch as early as possible. Get customer feedback. Odds are that the actual product that you end up getting traction on is a couple of pivots away from that first version that you go with.

So getting customer feedback and what Dave was saying around, having their, that customer trust and almost like building like an initial early adopter, like an advisory panel of customers, is super key here [00:10:00] because a lot of VCs and a lot of investors will directly speak to those customers to get their take on the product or their early versions of the product.

That's super key.

One strategy and this is coming a little bit more from the software side of things is design partnerships are is a really great asset on this front. To prove demand for something before you've actually built something.

What that entails is you pick an ideal customer that you want to work with. You approach them with this like design partnership agreement type document. And what that basically says is, hey, if we build you this in the future, will you pay for it in the future? And it's a nice kind of letter of intent to get them to solidify what types of features that they would want to be included as part of the MVP.

And there you go, there's your product roadmap. Design partnerships are a great way for you to validate your product roadmap and really show investors that you have some demand for the type of [00:11:00] product that you're going to build.

Yeah, I think iterating fast and keeping close with customers are the really big takeaways at this stage.

Q&A: The Criticality of Storytelling

Jimmy: Awesome. Thanks, guys. John, do we have any questions?

John: Yeah, we had some questions from folks when they registered. Pulling people into the organization, the right people, talented people, can be critical. Can you speak to what it took to bring someone who ended up being extremely valuable to you and your work onto your team? How did get the first couple of people who made a really big difference?

Zak: I think on this part this is a little bit where the storytelling comes into play, especially at this stage. A lot of times you can't rely on metrics or the amount of revenue that you had in the past six months because you didn't even exist six months ago. You really have to be a good storyteller.

And this is a key here, too, on the sales motion is it's you don't want to hire a salesperson too early. A lot of your [00:12:00] sales should be done by the founders, and you're basically practicing that sales motion both for your customers and for your early employees as well.

Really having a great story and a mission to align. You're not, especially if cash is limited, you're not going to be able to compete with the large tech companies in terms of salary or base comp or anything like that. So you're going to have to sell the story and sell the mission. That's something that you'll need to practice a ton in order to get right.

John: Yeah, that totally makes sense. Do you want to jump in with a thought there, David, or I have other questions too.

David: No, I think Zak hit the nail on the head.

John: Okay, so here's one that may be hard to answer. But what's something that you did, or you've seen people do, during this phase in your business's growth that like was a really bad idea. What was a mistake you made, time you spent, a decision you made, what was something that in hindsight you say, "Oh my God I hope no one ever does what I just did."

Zak: I've one that comes to mind right away. At Hearth, we hired a [00:13:00] customer success rep before we had any customers, and so unfortunately, when we had zero customers after, you know, trying to launch and get this thing running for about a month or so, that customer success rep had nothing to do. I think, basically, pre-launch or assuming that you're going to have some sort of traction with the products for your launch, you never know until you launch or put it out there.

That's what going back to my first point about just launching as early as possible. So you have at least some data. That's something when you're saying that early mistake that I hope everyone avoids. Definitely don't hire a customer success person or rep before you have customers.

John: Thanks, Zak. David, did something jump out at you?

David: Yeah. I'll talk to bringing on additional people to the team. Not necessarily employees, but more so co-founders or senior staff, who will have [00:14:00] a larger equity position than maybe others. My opinion on this comes from a few battle scars.

I'm a solo founder. I was a teenage solo founder. I've had other companies as well where I had co-founders. The truth is when you're looking for additional people to join your team, you're looking for people that can move the needle and complement your skill set. And I think, at least for me, earlier on, especially when you start digging into the VC statistics, and you're part of all these accelerators, and everyone else has a co-founder, it's very easy to start thinking about the fact that most startups that are getting funded have multiple founders and you have a whole team.

And there are a lot of positives to having a co-founder, but one of the mistakes that I lived through was trying to constantly bring on additional people to help me. And I still do this to this day, obviously, and we have a team in place, but I was very desperate early on to [00:15:00] find team members that had as much passion as I did, were willing to put in the amount of work and time and effort that I was.

And that's just not really realistic.

In the beginning. It's very easy to just throw away equity. It's very easy to just say, okay, I'm not taking the salary. I've got a hundred percent of this company, or I have a co-founder, I want to give them 30 something percent of the company or 25 percent or 50 percent. And that really comes back to bite you. Now, I never added a co-founder, but there were multiple instances where I was about to add a co-founder or about to add an advisor or a C-suite and gave them some sort of equity or was about to give them equity. And there are a number of ways you can curb your risk, but the thing that I found out that was probably one of the biggest things that I was, for lack of better terms, insecure about was the fact that I was a solo founder. And I knew as a teenage founder to this day, right, I don't believe I'm [00:16:00] the smartest person in the room. In fact, I don't want to be the smartest person in the room. And so in that constant seek for someone who could help me run the business, who had the gray hairs, who had the experience, I was constantly eager to bring people on.

There are a number of things that you can mention about what not to do and what to look for in those types of people that you're bringing on. But before you even get there, my biggest advice when it comes to this is don't rush to try to add on team members. It's okay to be a one-man show or maybe a two-person team or a three-person team. And it's okay to have interns or associates or junior people that can help lift some of the weight off of your back.

In no way, shape or form, you should be finding a co-founder or looking for a co-founder just for the sake of having a co-founder.

Seed to Series A

John: Awesome. Yeah. Thank you, David. So we're gonna jump on to the next phase of business [00:17:00] growth.

As a quick summary, stay close to the customer, get your story down, be really mindful about hiring or bringing on partners that could actually set you back, not push you forward.

What happens between Seed and Series A?

In this period, to eventually reach your series A, you need to deliver on some of the promises from the earlier phase. This means achieving product market fit and showing a clear shift in your growth curve.

So what's product market fit? One cheeky answer would be, if you're asking, you don't have it. When I've seen it happen, I've observed that growth is driven by one or two sales marketing motions, one or two primary motions. And, it's systematic. It's becoming systematic and repeatable. Growth is becoming more systematic and repeatable. It's almost mathematical. If you do X, Y, and [00:18:00] Z, then you reliably get output: more sales output.

The iterative learning continues in this phase, but I'd say the stakes are even higher. You need to figure out how to sell and market your product at scale while refining it.

A powerful technique for smart testing, this is getting a little tactical, is explicitly writing down the assumptions you're making. For example, one company I work with is testing outbound messaging right now, and they're assuming their customers are prioritizing coding speed. Getting through their coding faster. If correct, the response rates to the outbound messaging will beat a previous campaign that focused on their product quality over speed. So what I'm suggesting with this quick tactic is literally like going to the trouble of writing down your assumptions and then revisiting them when you're looking at your results.

At [00:19:00] this stage, you must confirm with sales evidence that you've found a large number of prospective customers struggling to make progress in a situation, in a specific situation, and that your product is the solution.

Unless you just luck out, this is going to take quantitative and qualitative customer data, things like interviews. The customer focus from the prior phase absolutely continues in this one.

And if I had to boil down business success to one thing, it might be understanding your customer's lives. That's true of every phase.

When you're increasingly successful with your sales and marketing and product experiments, don't lift your head up to see that every other part of your world is falling apart.

I take to heart David's comment that you don't want to be bringing on people too early but don't bring them on too late, either. Try to find the sweet spot. [00:20:00] You may need to grow your team at some point. And hiring the wrong person in this phase also, either the wrong person because of role, which Zak spoke to not needing someone in a certain role at all, or cultural fit or fit with you can really set you back many months.

Be intentional about what you stand for and what qualities matter in hires. And remember, not everyone needs to be full-time. There are a lot of flexible models for bringing on support these days. So this caution about raising your head to find things have gone awry applies to things like HR, legal, financial management, other ops, a complete lack of attention to these areas can cost you more time and money than doing the basics right to start.

And I'm not talking about perfection.

I'm just talking about good enough. Just make sure you're paying some attention to these [00:21:00] operational matters. Things like payroll-related snafus or neglecting confidentiality agreements and IP assignments: these can be huge nuisances, later when your business is growing.

By the end of this phase, there's still room for business model tweaks. However, it should be clear what problem you solve, what resources you need to deliver your solution and whether that's financially viable at the scale you're looking for. Showing hockey stick revenue isn't going to be enough if you're lucky enough to have gotten that far. Investors want proof that you can scale profitably with reliable customer acquisition and sustainable economics, even if you're still burning cash at the present moment.

So to raise your series A in the next phase, you're going to need to demonstrate you've figured all this out and that, and on top of that, that you can systematically grow the business up to a hundred times from where you are at the [00:22:00] end of this phase of your business growth.

With that, as we did for the last phase, Zak, why don't we start with you? Could you share some of your personal personal experiences or insights? Applicable to the Seed to Series A stage.

Founder Experiences: Tracking and Testing Your Assumptions

Zak: Yeah, for sure. I think there are a couple of different points I want to hit on. John, you were mentioning a bit about starting to capture data and write down assumptions and learn from different tests. I think. At this stage, it's crucial now that data is starting to pull in about usage, customers, things like that, that a constant testing and data-driven culture is built up within the organization, whether it's right, running A/B tests on a particular landing page as part of a sales motion, or running different tweaks or tests within the product itself to make tweaks there.

And you're going to start off with small numbers. You're not going to have statistical significance on these tests at [00:23:00] first, but you're basically building that muscle and then keeping track. And going back to the writing things down, so you never forget them, write down what tests you're running, what assumptions you have prior to the test and the results of that test.

You're basically building up this directory of all the past tests that have been run. You'd be surprised, if you keep that record over the course of three years, how many times a previous idea that you tested will come up as a new idea in some meeting.

You go back to it, you might have different numbers of users that you have 10 times the amount of users. So maybe you'll try it again, but at least that'll be the new assumption for that next test.

Transitioning this into the types of people you want to bring into the company, you want that hungry kind of culture fit type people that are data-driven. When it's chalked up between a kind of hungry person versus a so-called industry expert at this stage, you might be drawn towards the industry expert. But you're trying to disrupt the industry that [00:24:00] expert is an expert in. You might want to bring them on as an advisor and take a little bit of their expertise, but you don't want to rely and go with, "Oh, this is the way it's always been done. So let's just do it this way." I think if you're trying to disrupt an industry, you want to take the best parts of advice from those experts, but don't look at them as the source of truth as to how things should be done.

One kind of anecdote on this slight pivot and testing data-driven culture: our first kind of customer that we were marketing to was homeowners for home improvement loans. We basically were trying to match up homeowners with different home improvement loans and projects and things like that. We made one slight tweak, not to the product, but to the actual end customer that we were doing the initial marketing to. We ended up switching gears towards and trying out this as a test: "Hey, why don't we market this product to home improvement contractors because when they're in the house of a homeowner giving a bid that homeowner is a very high [00:25:00] intent to potentially take out a loan for a home improvement project."

That's just a slight tweak. We didn't change the product. We just pivoted slightly who the end customer is That allowed us to get more of a pull for our product market fit as opposed to a push in terms of all the campaigns that we were running. You still want that testing culture. When you start to feel like a pull from your customers, that's, for me, my sign of product-market fit that's starting to appear there.

John: David, did you wanna jump in?

David: The only thing I would add, because Zak once again gave a pretty comprehensive overview, the only thing I would add in or double down on is simply the fact that at any stage, really, and in my opinion, at least as a Series B company and prior, your main goal is to hire A-plus players.

We still do this today.

I was talking about it this morning. We'll, for the foreseeable future, continue to hire this way. There's something to be said about hiring people who [00:26:00] have industry weight, but the truth is, you want to hire for attitude, not aptitude because you can teach the aptitude portion of it, fairly straightforward.

And the attitude is something that you can't teach. So if you have the choice between someone who has little to no experience in the industry versus someone who has a ton of experience in the industry, but the difference is the person who has a ton of experience is a C-suite, or wants to be like a C-suite, and does not want to really do work and wants to build a team and have his team do the work and he just plays chess master. In a small startup and even in a midsize startup, it's very unlikely that is going to be beneficial to your company because, as you're trying to build, your main priority should be to execute and make mistakes as quickly as possible and then reiterate and make those same actions again.

And hopefully, this time, the second time around, you're not making mistakes.

So in order to do that, you need less time thinking, strategizing and sitting there and pondering about what [00:27:00] you could or should do, but rather, you should take the person who's just willing to put the pedal to the metal. And, honestly, just try to get as many, wins as possible. Whether or not they're 100 percent accurate and doing the right thing, I think, is secondary.

Let your team make mistakes, let them go ahead and learn on their own. My opinion is that is a much better approach. Someone who's obsessed with what they're doing and not necessarily knowledgeable about it is far more dangerous than someone who is incredibly knowledgeable but does not want to actually put in the effort to make the needle move.

And that, believe it or not, is a much more common occurrence than you would think.

John: I know one of the things we talked about back in the day a little bit, David, was just like, yeah, hiring a salesperson. This wouldn't be true in every case, but there could be a case where that industry expert in the incumbent culture and the incumbent model is actually really a bad fit, for someone who's trying to change everything.

David: [00:28:00] Yeah, Zak said it, right? You're trying to disrupt the industry. So why would you hire a person from the industry? There are benefits to doing that, and in certain positions, it makes sense to do that, but in the grand scheme of things, you will oftentimes, more often than not, find that the person who's in the industry, who's been there for 10, 20, 30, 40 years, is likely going to come in with the same ideas that have been done for the last 10, 20, 30, and 40 years. And that's not what you're doing. If you're trying to be different, And building a team that way and building a company that's revolutionary, you will need revolutionary approaches.

Q&A: Making Critical Hires

Jimmy: Awesome. One question that we received from our attendees was what are the most critical roles to hire and when during this phase, and is a technical founder critical, or can you rely on an outside dev?

Zak: I think it really depends on the type of company you're building. I guess the answer is a bit nuanced in that sense. Maybe one distinction that could be helpful is there are, [00:29:00] within kind of the tech or kind of software ecosystem, there are tech companies, and then there are tech-enabled companies. And so if you are a technical company you definitely need a technical co-founder.

But if it's a tech-enabled type services business that you're layering tech on top of or something of that nature, then you don't maybe fully need that technical co-founder. It really depends on the business.

But I guess my more general advice is to try within your best ability to do any and all roles and wear as many hats as possible. And you should be at least getting a first stab at the role that you're trying to hire for yourself. So you should be trying your best. Obviously, it's a little bit harder if you don't know how to code, but definitely, at least for other types of roles, marketing and sales, you got to wear those hats and try it out yourself. Then only when you're completely booked time capacity-wise do you then outsource to a [00:30:00] person?

Jimmy: David, any additional thoughts on that question from you?

David: No, I think you have to have some knowledge about almost every function as a founding team. And the truth is under 10 people, even under 15, every person in the company is going to have to wear multiple hats.

As a founder, especially if you're earlier stage, your goal should be to be dangerous enough to understand what anyone else tells you. You don't have to be an expert. For example, you don't have to be an expert software developer. I have a physical goods, industrial enterprise company in the advanced material space.

So it has nothing to do with coding. But because in the early stages, we were going through so many iterations of websites, and we want it to be that new age startupy company, and we want to have a better than usual website, I learned how to code just enough so that I could make modifications, basic things, on my WordPress site.

That isn't always necessary, [00:31:00] but I think, the more that you can do that, it does two things. One, it makes it a lot more scrappy and resourceful as a company for you as a founder and for all your team. Two, it also makes sure and gives you some schmuck insurance to make sure that you're not being told one thing that isn't, and you can really validate.

David: It's like for anyone who's worked on their home before and made home improvements. If you've done a replacement of the floor, and you know what effort goes into, let's say, resanding hardwood floor and an expert comes in, a flooring expert comes in and tells you that it's going to cost 25,000 to redo your floors, you can weigh the options and understand, okay, is that really worth it?

Because I, if I do this myself, I have to do X, Y, and Z and sure I might save 25,000, but is it really worth it?

It's the same concept. If you know what it takes to do sales. As hard as that is, especially if you're not an extroverted person who enjoys doing cold calls or meeting people or whatever the case may be for your [00:32:00] specific sales process. If you don't enjoy that particularly, you'll value it more when you find the right salesperson.

It also will mean that when you find someone else who doesn't really scream that perfect fit, who's a great salesperson, that you're not going to rush to hire them as one of your first few hires, just because it was one of the first few people that you interviewed and you could find, right?

It gives you that callousness that allows you to then say, "Okay, I know what it takes. I know what kind of personality you need, I know what type of metrics I need to hit, is this person the right fit, and is what they're telling me actually going to work."

Series A and Beyond

Jimmy: I get you that makes perfect sense. We'll continue to move, and then we'll leave a few minutes more for any additional questions that anyone has. I'll just give an overview here, and then we'll again hear from Zak and David on more specific examples.

By the time you reach a Series A, things start to look different. You've proven that your customers want what you're building. [00:33:00] You've secured funding, you built a team that believes in the mission. Perhaps things start to shift here in terms of scaling, right? And so scaling isn't just doing more, it's doing it better, faster and at scale.

So the scrappy founder-led execution that got you here won't get you there.

At this point, you're no longer building a product. You're really building a company. And the focus is now more on repeatable growth. So instead of testing the waters, you're now turning early traction into a scalable operational engine.

Three shifts here that I'll outline. So going from a founder-led hustle to scalable execution, right? You need systems processes and a leadership team that can operate without you having to make every call.

And then earlier going from early product market fit, now, you're going to more sustainable growth, finding repeatable go-to-market strategies, refining your sales process, [00:34:00] ensuring customers don't just convert, but they stay.

Also, going from a small, nimble team to a structured organization. So teams expand, roles specialize, and cross-functional collaboration becomes a necessity.

Some of the challenges right here are more about operational growing pains, so more teams, more customers, more evolving parts. Suddenly something that was messy has gotten just messier and misaligned. The founder role evolves, and so up to now you may have been involved in everything in the weeds, leading sales, making product calls. Now you're letting go of some of that and starting to build a leadership team that can execute without you being involved in everything.

And then expanding without losing focus. Do you go deeper into your existing markets? Or do you expand into new verticals? That's a question that startups really start to think about at this phase. So growing too fast can kill your momentum. Moving too slow can [00:35:00] stall you, and competitors can sweep in and get that other part of the market.

Here, the bridge really is about building those strong cross-functional teams. Sales and marketing and product have to be aligned, they have to be on the same page. Sales can't be telling customers one thing. Product is off, building, building something completely different.

Those silos really start to stunt your growth as an organization. You have to operationalize your culture. That really means that the values and the mission that you had your early employees and customers behind, now, you have to do that at scale.

So, really codifying your culture into your hiring, into your onboarding and leadership training, so then the culture doesn't just become a billboard.

And then prioritizing the product roadmap, right? What got you early traction may not be what carries you forward. So your product strategy has to evolve with the company.

Let's again open it up to David and Zak. [00:36:00] And maybe, David, I know you had chuckled. We can start with you and get your thoughts on, this phase.

Founder Experiences: Don’t Ignore Culture

David: Yeah, I think the first thing, based on my experience, is everything that you think you're going to do, everything that you put in your business plan or your conceptual ideation phases in the very beginning, is all wrong.

That's the only thing that you can be 100 percent sure of is that you're going to be wrong. That's okay. In fact, that's a good thing. Your company needs to evolve, and your culture will evolve over time.

I think it's super important that when you're hiring, culture has to be super aligned. That's not that simple to do. I think when you get bigger, when your company starts to grow, when you start bringing on people, you'll start to realize that culture is a lot more complicated than [00:37:00] here are my mission, vision and core value statements, and everyone should adhere to these.

It's far more complex than that, and it's also far more important than just that because when things get really tough, that's when culture really matters. That's not something that most people talk about. The culture isn't important because it's all kumbayas sit in a circle. We're all going to have fun and build this great thing. That's not why it matters.

It matters when you've got a customer who's calling you at three in the morning because you have a major blow-up in their system, whether that's software or physical goods. Especially if you're in enterprise sales, you're talking seven, eight-figure deals at a time that take years to build and just one screw-up to lose forever.

Even for small businesses, it's the same. It's the truth. Like we're going through a CRM shift right now, and it's all because one mistake that our CRM made. It's the case across the board when anyone is dissatisfied. They're far quicker making decisions to eliminate that solution that they're currently [00:38:00] using for something else.

That's when culture matters the most. When these times that are incredibly difficult, and they will happen, no matter what company you are running, there will be certain disagreements. There will be issues that come up, and culture matters then the most because that's when people will step up, provide solutions, and really act like they're owners of the company and care for the company like it's their own. That's the biggest thing that you want out of a good culture.

It's not the fact that you want to enjoy coming to work every day. That's important too. Don't get me wrong. But the truth is, when everything's gloomy and not fantastic, that's when times get really difficult as a founder, especially if you're a solo founder because you've got no one else to go to. That's when you need people to step up and bring a whole new approach.

But if they're not interested, if they're just in this for a paycheck, and they're used to the status quo, and it's just a company that they're at. And sure, they [00:39:00] align with your mission and vision, and they think it's cool, but it's not the forefront of their mind. They're going to waiver. And you're not going to get the level of output and dedication that you might be looking for out of an employee.

Zak: Just to double down on how important culture is.

I think the big competitive advantage that you'll have at this stage is that you're still lean, you're still coming after the A and the Seed, facing incumbents in the industry that are bogged down with processes. They're bogged down with meetings. And so trying to keep that lean mentality for as long as you can is super important here.

I liken culture to this concept where a good culture replaces like a few different processes here and there. For example, if you just have a strict 9 to 5 policy, and that's in someone's mind when they receive a phone call at 6 p.m., there's an "if statement" in their head, computer science person nerds thinking, "If statements" here. But if there's a [00:40:00] process that says employees only work from 9 to 5, then that person's not going to pick up the phone. Whereas if the culture is if customers are important, you pick up that call, you don't need a process or a rule there that it's nine to five. You just trust that people are going to do the best thing for the company.

One great book on this front is the Netflix one, No Rules Rules, where it's takes it to the extreme, where if you're just so bought in on this culture, you actually don't need to approve spends for employees who are going to travel. They know they're not going to take first-class tickets because that's going to negatively affect the company.

I think the more you emphasize culture here you can prolong the time at which you need to grow up as a company. You maintain that startup culture and really are able to continue to have that trust in your other teammates.

One other kind of quick anecdote here that I emphasized as our team grew is make sure every single employee, as you start to create different layers and the org structure starts to [00:41:00] grow, make sure for every task, every single person knows the why behind why they're doing that task. They're not just a robot picking up this task because it's in Asana or Jira or whatnot. They need to answer, Why are you working on this? Why is this important to the company? That just reinforces that culture that they're all moving towards the same collective vision there. Yeah, just another double-down on how important culture is at this stage.

Q&A: Is any Investor a Good Investor?

John: So one of the questions was, What should you work hard to protect that may get lost in transition from Seed to later stages, and I think part of the answer is culture. If you get it wrong earlier, it's going to come back to bite you now, and you probably need to work hard, I'm inferring from what you both shared, you need to work hard to keep it so it doesn't get lost as you grow.

Another question is, and this may be applicable to any stage, the final question [00:42:00] from the chat and the pre-questions, is is any investor a good investor or do the investors matter?

Zak: Anyone want to take it?

David: Yeah, of course, investors matter.

That's a tough question for any founder to answer because, on one hand, in most cases, you want, in an ideal world, you don't have investors, and you bootstrap it. You build a nice medium sized business, you exit or hire. That's not super realistic for most companies. That's okay.

As a result, investors matter in any event, because even towards the end of let's say a middle-sized business, most of the companies that you're going to be working with in an M&A transaction, whether those are M&A brokers, whether those are private equity groups, whatever the case may be, all of them will speak the same language as the investors do.

So, [00:43:00] even if you don't plan on raising venture capital or angel money, what's important about investors is how they think. Because most of them are just the same Patagonia vest-wearing bros from college that have a lot of merit and a lot of financial backing.

But the best part about it all is that it's copy and paste with most of them. You can pretty much, 50 percent hit or miss, take one group of investors and apply that same level of logic to the other group. Or if they're polar opposite, then they're going to find their own groups. They all flock together. Like it's the biggest conundrum in investing in the startup world, where FOMO is the biggest thing that you can create as a startup when you're raising capital.

The main reason is just simply because they all act and think the same. Or if there are some that are leading the charge and are opposingly different, that's great. They have their own clique as well that's just like them too. So the reason why all that matters is simply that they're a great resource, and [00:44:00] they're phenomenal, even if you don't want the capital from them, in helping you navigate what a transaction might look like if you're looking for acquisition. Now, if you're not looking for an acquisition, if this is like a mom-and-pop business that you want to run, a family business, that you pass, that you plan on passing down, then yeah, of course, then do whatever you think your small business needs. That's the way to do it.

But if you're in any other case where you are raising capital, or you're even considering potentially bootstrapping, the investors are important, and they're not important because they're just writing the check for you. They're important because they'll have governance and control. And you don't want to, you want to play a fine line, right? You want to make sure that your investors are on your team, but you still have the autonomy to run the business how you want to run it. Just be aware that if you make enough mistakes, you're replaceable.

That's all.

Zak: One thing, one thing I'll add to that is Investors also come with their own Rolodexes. And so [00:45:00] that's one thing to optimize for as well. So for instance, if you're starting a company in a niche space where there's only kind of four major VCs that operate in that space, well, talk to them because not only could they give you funding, but they could also introduce you to their portfolio companies that end up being your first 10 customers.

That's just something to keep in mind as well. You might have two offers from two different VCs, but there's a lot more that's behind that money that could be of an advantage to you. So one, one quick note to add there.

Conclusion

John: Yeah. Hey, Jimmy, do you have anything to add? And then we can, we do have a takeaway and a few things to share before the end of the call here.

Jimmy: Yeah, just want to say that thanks to everyone who was able to make it, and we'll definitely send out the summary of this chat to everyone who registered. So, if you join late, you'll be able to get some of the earlier key points.

John: Zak, you came off mute there.

Zak: Yeah, I came off mute. [00:46:00] One final thought is people are a lot more willing to help, so long as you ask. If you need advice on something or whatnot, you gotta ask first, but you'd be surprised how much people are willing to help, even if it's just their own two cents on something.

It's better than nothing.

David: That was my exact, that's exactly why I came off mute as well.

John: Awesome. David, Zak, thank you so much. We really appreciate you sharing.

And Jimmy, it's been a pleasure. I think we're good. Thanks.

Jimmy: Thanks. We'll send out a note on part two of this series in a couple of weeks.

Please reach out with feedback about the event.

Read Part 1 of the second event in the series: Series A Is a Reckoning: Operator Imperatives for Getting to Series B

John Gauch 2024-01-02 John Gauch 2024-01-02

50 Top Apps, SaaS Solutions, Services and Sites for Startups

Startup CEOs and founders are very demanding when it comes to the tech they use to run their businesses. They have high expectations. They should, too. See how this list of apps, SaaS solutions, services, and sites lines up with your tech stack and hopefully get some new ideas for what to add or switch.

Updated May 30, 2025, including the AI apps everyone should be using or experimenting with.

Image for blog post about list of top tech for startups — Photo by Magda Ehlers from Pexels.

I hope you find this list helpful - I'm John Gauch, a consultant with extensive experience in business operations and growth. I specialize in helping startups implement both strategies effectively. As a fractional COO, I work with founders and CEOs through each step, tailoring solutions to your unique needs and objectives.

Updated May 30, 2025.

What started as a list of 50 startup apps has grown well past that figure, and I’ll keep adding to it.

I personally don’t find those lists or infographics of every possible option for a problem super useful. I don’t need another time-sucking To Do, to evaluate all of the choices. I want to know what’s a reasonably safe bet, get started with it and turn back to the business of growing my company.

With regard to each product on my list, I've either used it, and I recommend it, or someone I know and trust has used it, and they recommended it to me. The list is biased toward Seed to Series A companies because that’s where I spend most of my time, although it includes some products for brand-new companies (drawn from the venture studio work I do).

That said, feedback is invited—if you feel like something should be added, or if you have used one of the products and had a negative experience. Email me and let me know.

I don’t mention project management tools (e.g., Asana, ClickUp, Monday, Trello) because everyone seems to have a favorite, and they all seem reasonably decent. I use Trello for my personal task tracking. I wouldn’t spin too long trying to ascertain which one of them is “best.”

Again, if your choice of a new web app (etc.) to add to your startup’s tech stack is not going to make or break your business, don’t over-index on it. Do some quick research. Get together a couple or a few ideas. Do a brief analysis. Pick one and turn back to the activities that are going to be far more impactful on your organization and its success.

That’s the benefit of having a list like this. I hope it helps.

Top Startup Tools

Product	Description	Other Options
1Password	Password management and security
Ahrefs	Ahrefs for SEO analysis and backlinks; AlsoAsked for keyword analysis on competitors and search term difficulty	Semrush	Also Asked
Airtable	Collaborative work management
Amazon AWS	Cloud computing
Apollo	List building from search critera. Send sequences. Consider checking out new kind on the block Unify. Fiber AI is the same idea but for recruiting	Unify	Fiber AI
Arc Tech	Treasury services
Bill.com	Billing and financial automation
Brandpad	Brand development and management
Brixx	Financial forecasting and planning software
Carta	Equity management and valuation, but watch the latest news about them	Pulley
ChatGPT	ChatGPT remains my go-to GAI tool. I list Perplexity but have heard mix reports recently	Claude	Perplexity
Clay	Import lists and enrich them (more options than Apollo). Consider also checking out newcomer Unify	Unify
Clerky	Legal and compliance solutions (company setup)
Clockify	Time tracking
DailyBot	Slack stand-ups
Deel	Global payroll and compliance. Deel is an EOR that recently purchased a PEO
DocSend	Document sharing and tracking (for a fundraising, DocSend + Dropbox or Google Drive + Google Sheets for tracking)
Docusign	Electronic contracts
Fathom	AI notetakers	Granola.ai	Fellow.app
Expensify	Expense management and tracking	Tentative: Float (Canada)
Figma	Design and prototyping
Flowster	Workflow automation and processes
Freshworks	Customer engagement and support software	Zendesk
GitHub	Software Engineering version control and collaborative software
Google Analytics	Website analysis	Hotjar
Google Workspace	Collaboration and productivity tools (email, storage, etc.)	Dropbox (storage only)
Grammarly	Communication assistant including AI support
Greenhouse	Recruiting and applicant tracking	Breezy	Recruitee
Guideline	401(k) providers	Human Interest
Gumloop	AI-driven workflows; AI agents/operators	Lindy AI
Gusto	Payroll, benefits, and HR services	Humi (Canada)	Rippling
Hubspot	Customer relations management (CRM). To include LinkedIn in your sequences, try Dripify	Dripify
Indinero	Bookkeeping service. The Bench recommendation is tentative	Bench
Intercom	Customer messaging and support
Jenkins	Open-source automation server for continuous integration and delivery (CI/CD)
KnowBe4	Security traininig
Linear	Issue tracking and project management
Loom	Video messaging
Luma	Event registration and management
Mercury	Banking for startups and businesses. Consider Mercury credit card too	Bluevine
Microsoft Azure	Cloud computing platform
Microsoft 365	Productivity apps (still use them as good as Google is)
Miro	Online collaborative whiteboard	Excalidraw
NeverBounce	Stand-alone email deliverability solution
Newfront	Insurance brokerage	Founder Shield
Notion	Collaborative workspace for your organization, with built-in AI support
Okta	Identity and access management
PaperStreet	Investor updates
Pave	Compensation information for startups
PitchBook	Data and research for private investments
Quickbooks	Cloud accounting software. Also hearing increasingly about Campfire in this category	Xero
Rippling	HR PEO	Justworks
Ramp	Corporate card and services. Brex may not be an option for smaller startups	American Express	Brex
Scribe	Creation of SOPs and internal documentation
Secureframe	Compliance and security automation
Segment	Customer data platform
Secureframe	Compliance and security automation
Slack	Team messaging
Stripe	Online payment processing and business tools
Supernormal	AI tool for meetings
User Interviews	Customer research
VPM	Virtual mailbox
Vouch	Business insurance. Also Embroker	Zen Insurance (Canada)	Hiscox
Voxer	Team audio messaging
Webflow	Website design and development
WeWork	Co-working (in bankruptcy but still operating)
Wise	Foreign exchange
Wordsmith	I am looking at these AI legal tools now	Pincites
Yubico	Hardware security keys
Zoom	Video conferencing

While the companies aren’t vetted, another interesting place to search for potentially valuable services is the Y Combinator community of companies.

If you’re a startup CEO or founder, and you feel it would be interesting to chat, I’d love to connect. Learn about my services and please reach out.

John Gauch 2023-09-12 John Gauch 2023-09-12

How to Learn Jobs to be Done

Find out how to get started with Jobs to be Done, do your first JTBD interviews, get colleagues on board with the concept, and deepen your outstanding of the framework, methods and tools--to start and grow a business and align a team.

Photo representing someone navigating their Jobs to be Done learning journey — Photo by Leah Kelley from Pexels.

In case this is your first time visiting - I'm John Gauch, a consultant with extensive experience in business operations and growth planning. I specialize in helping startups implement strategies effectively in both areas. In my work as a fractional COO, I work with founders and CEOs through each step of the process, tailoring solutions to fit your unique needs and objectives.

Creating and sustaining a successful business entails doing countless things right. Knowing the Job to be Done (JTBD) of your customers and how your product helps them may not make it easier to start and grow a company, but it will make what you should be doing more obvious--and less subject to guesswork.

Co-architected by Clayton Christensen and Bob Moesta, a "Job to be Done" is the progress someone is trying to make in a struggling situation. Putting the JTBD framework to use effectively requires a commitment to understanding people's lives.

It is less about, "How do I make people want my product?" More about, "How do I make a product people want?"
It is less about, "How do I 'sell' more of my product?" More about, "How do I help people make the progress they are seeking?"

Applying the JTBD framework tells us why people pull your product into their lives, how to communicate with them compellingly, and how to satisfy them after they make a purchase. It can also tell us whether a brand new product idea is likely to work or not. In a May 2012 interview with Horace Dediu, Christensen contemplated: "10 years down the road, people will look back at my research, and they might say this idea of Jobs to be Done is a bigger idea than was 'disruption'," the theory that initially brought Christensen to the business world's attention.

Today, people around the globe put JTBD to use at companies of all sizes across industries.

Not only will applying JTBD and the associated mindset help you grow a business and innovate. When combined with practices and tools such as customer experience mapping and complementary metrics, leaders can articulate a clearer vision, dial in the organization's value proposition, align the team, and develop accountability among team members.

To learn all about JTBD, and how do do and use customer interviews, read my series of posts on the topic at Medium.

If you’re a startup CEO or founder, and you feel it would be interesting to chat, I’d love to connect. Learn about my services and please reach out.

This blog post appeared originally on LinkedIn.

John Gauch 2023-08-29 John Gauch 2023-08-29

Estimating Product Market Opportunity

I often scratch my head trying to understand the market opportunity described in many startup investor presentations. I’m not saying it’s easy to measure by any means, and in this post I lay out an alternative way to to think about and calculate this popular figure.

Image showing common desk tools representing the analysis required to determine a product's market opportunity — Photo by Karolina Grabowska from Pexels.

First time here? I'm John Gauch, a consultant with extensive experience in business operations and growth planning. I specialize in helping startups implement strategies effectively in both areas. In my work as a fractional COO, I work with founders and CEOs through each step of the process, tailoring solutions to fit your unique needs and objectives.

TAM (Total Addressable / Available Market), SAM (Serviceable Available Market) and SOM (Service Obtainable Market) are popular conventions that we all see in investor pitch decks.

TAM can loosely categorize opportunity scale (large, medium, small), for example.

I am really interested in a figure sometimes captured in the SAM or SOM, but this is case by case depending on how people calculate them.

The market opportunity number I like to see is this:

Equation for alternative market opportunity calculation

Specifically excluded from the number:

I do not view this as a static figure. We can update it if/as our customer understanding changes. We can also handicap the number to reflect the likely prospects today, versus those experiencing barriers to purchase due to access, cost, skill or time, for instance.

I am not saying this is easy math or we can do it with absolute, scientific precision, but there is a ton of value in just trying. Calculating market opportunity in this way requires understanding:

the specific problem a product helps customers to solve
the situation when that problem arises
the better way customers are seeking

To uncover these often-hidden customer insights, we can use lean approaches, such as interviews, which go beyond what we can learn in a survey or focus group.

Read also: How to Learn Jobs to be Done

What we discover will inform a lot more than a market opportunity number. It will likely inform our strategy, product and marketing approach, helping us to build and scale our businesses.

If you’re a startup CEO or founder, and you feel it would be interesting to chat, I’d love to connect. Learn about my services and please reach out.

This blog post appeared originally on LinkedIn.