At my recent event, “The Other Side of the Exit: Is There Happiness Beyond the Deal?” Greg Head shared his perspective on what software founders face when building and exiting businesses. As someone who has spent decades in the software industry, Greg spoke candidly about the changing dynamics of entrepreneurship and the real choices founders can make beyond the push for rapid growth and large exits.

Rethinking Venture Capital

Greg started by addressing one of the biggest myths in the startup world: that venture capital (VC) is a must for success. “The myth of modern software is you need funding to do it,” Greg said. He pointed out that many founders believe funding is the only way to grow, but in reality, there are many alternatives that allow for growth without losing control. Greg has worked with numerous founders who have built and exited companies without massive funding, but their stories are less visible because they don’t fit the traditional narrative.

“VC funders are selling you their drug,” Greg noted. Founders often think they need to raise capital to succeed, but they don’t fully understand what it means to invite investors in and give up control of key decisions.

The Hidden Majority of Founders

Greg emphasized that the majority of founders are building solid businesses without the need for large amounts of funding. This “hidden majority” may not make headlines, but they are running businesses that are both profitable and fulfilling. “There are so many ways to do it,” Greg said. “You can grow fast, grow slow, be profitable or not. There’s no one-size-fits-all.”

His message was that founders don’t have to follow the same path as others in their industry. Whether they choose to bootstrap or raise money, what matters is finding the right approach for their specific business and goals. And the big secret is they often end up with more money in their pocket post-exit than they those who get VC funding.

The Cost of Control

Greg warned that founders who take on outside funding often don’t realize the extent to which they will lose control of their companies. “When you raise money, you’re inviting people into your house to tell you what to do,” he said. Investors can quickly become the primary focus, taking attention away from customers or employees.

This loss of control is especially clear when founders are preparing to exit their businesses. I shared the story of a client who felt completely overwhelmed by last-minute demands during the sale of his company. Greg explained that this is a common experience for founders who have outside investors. “That’s normal. Selling a company is one of the most stressful things a founder can do,” he said.

Bootstrapping as an Alternative

One of Greg’s central points was that bootstrapping is a viable and often preferable option for many founders. While bootstrapping comes with its own set of challenges, it allows founders to maintain control over their companies and grow at a sustainable pace. “Bootstrapping is hard, but so is raising money,” Greg said. “It’s just a different kind of hard.”

He also noted that the software industry has evolved in recent years. With the costs of building software decreasing significantly, founders have more opportunities to grow successful businesses without the need for external investment. This shift has given founders more control and more options than in the past.

Of course there is more external money than ever before as well, which means that the promises that investors make have become more and more extravagant.

Building for the Long Term

Greg encouraged founders to think beyond quick exits and to consider the long-term benefits of building sustainable companies. He noted that many founders feel pressured to sell because that’s what outside investors expect, but he urged founders to consider running their companies for the long term if it brings them personal fulfillment.

“What if you could keep running your company in a way that’s healthy and sustainable, without the pressure to sell it for $50 million or $100 million?” Greg asked. Many founders, he said, enjoy the process of building and running their businesses and shouldn’t feel forced to exit unless it aligns with their personal goals.

Opportunities in Niche Markets

Greg also highlighted the opportunities available in niche markets. He explained that 50% of software companies in North America now focus on vertical markets like real estate or healthcare. These businesses may not grow as fast as others, but they are often more sustainable and profitable in the long run.

“You no longer have to be one of the top three players in a huge category to succeed,” Greg said. “You can build a $5 million annual recurring revenue business in a niche and sell it for $25 million. That’s life-changing for most founders.”

The Unicorn Myth

Greg challenged the notion that every founder should aim to build a billion-dollar company. “Unicorns get all the headlines,” Greg said, “but 99% of VC-funded companies never come close to that.” He pointed out that most exits for tech founders fall in the $25 to $75 million range, far below the billion-dollar valuations often celebrated in the media.

“A lot of those billion-dollar companies leave the founder with far less wealth than they would have made selling a smaller company for $50 million,” Greg explained. His advice: focus on building something sustainable and meaningful, rather than chasing unicorn status.

Conclusion: Founders Have Options

Greg underscored a crucial message for founders: there is no one right way to build a company. Whether you choose to bootstrap or raise funds, whether you grow fast or slow, the key is to know your options and make decisions that align with your values and goals.

“Building a business is hard, but you can choose your own path,” Greg said. His insights remind founders that the ultimate goal isn’t just about scaling or selling—it’s about building something that works for them.

Does this resonate? If you are in the software world, feel free to reach out to me for an introduction to Greg or others in the space. And if you are a founder looking to connect to other founders, we’re building something there as well. Reach out to learn more.

As a founder, the journey to selling your company can be exhilarating. Many entrepreneurs work tirelessly with one in mind: an exit. The vision is simple — build something valuable, sell it, and reap the financial rewards. But what happens when the deal is done, and the dust settles? What do you do when you’ve won the game you were playing?

The Reality of Post-Exit Life

I recently spent two and a half uninterrupted days with a client who had just sold his company. He had many questions about what was next. This isn’t uncommon. In fact, it’s one of the most important conversations founders face after an exit. Before the sale, you’re laser-focused on growth, impact, and the ultimate transaction. But after the sale, a new question arises: What’s the next game you want to play?

For many founders, life after an exit is very different from what they imagined. The sense of fulfillment that they expect, for example, may not come. Instead, they may feel a sense of uncertainty or even emptiness. This disconnect is compounded by others around you who may not fully understand your experience. There aren’t many people who understand the letdown a founder can feel even after a big check.

There are often feelings of disappointment with the deal or frustrations with the new role in the acquiring company (as happened with my client). The reality of post-exit life can be much more complicated than expected. The money doesn’t change everything (or at least anything of importance), and the existential questions of path and purpose become more prominent than ever.

The First New Game: Embrace the Uncertainty

For the exiting founder, the first challenge is that there is often no clarity around what comes next. Maximize the earnest? Leave now to start something new? Quit everything for good? It’s easy to rush into the next project, but I encourage founders to embrace the uncertainty and use this time to explore, experiment, and be curious.

As I told my client, this is a period where you can afford to be unsure. You don’t have to wake up every morning knowing exactly what’s next. You’ve earned the space to try new things, to test out ideas, and to see what feels right. It’s about trusting the breadcrumbs that show up along the way and seeing where they might lead.

I had been wanting to go out on my own as a coach and trusted advisor for many years, but when I was first laid off from my corporate job in 2016 I kept chasing consulting gigs, thinking that I wasn’t prepared to make a full-time living from coaching.

The universe seemed to have a different opinion. Every time I went after consulting work, I got a hard “no.” But people seemed really happy to have coaching conversations with me, even though it took awhile before people started being willing to pay me. By trusting the flow, and being patient, I created a business coaching founders, even though I had never been a founder myself. But each of my clients, like me, had a spiritual openness and a history of seeing the world differently than most of the people around them.

Be patient, be yourself, and your path will unfold.

Another Game: The Joy and Purpose Game

One of my favorite questions of an exited founder is, “What do you want when you don’t need anything?”

For most people, life is more about wants than needs but they have created it in a way that a certain amount of income, a certain position, a certain lifestyle feel like absolute needs.

But for the founder, that illusion is shattered in one transaction.

Finally, they are able to see many of the possibilities that they missed while they were missing their business. And whether it is giving back, deepening relationships, exploring hobbies, or even building another business, the founder can create what is next much more intentionally, and finally live the life of joy and purpose that they thought they might get playing the founder game.

Can You Relate?

Does this resonate?

If you’re in the same position, where you’re asking, “What now?” after your exit, know that you’re not alone. It’s a time of immense opportunity but also one of uncertainty. The key is to trust yourself and allow the space to see what evolves.

And if you’re looking for a community of like-minded founders who are navigating this same question, I’m building something for exactly that. Whether you’ve had one exit or five, this is a conversation that matters.

If this resonates with you, reach out. I’m putting together a community for founders who are in this phase of their journey — exploring, experimenting, and figuring out the next big thing. Whether we have a short conversation now or I just keep you posted on what I’m putting together, I would love to make sure that you know where you can go when the time is right.

When Townsend Wardlaw agreed to be part of my event, “The Other Side of the Exit,” he confessed that his own exit had been “less than spectacular.”

But that didn’t stop him from trying.

And it didn’t stop him from trying again.

And it didn’t stop him from building a business where today, he advises other founders on how to do better in their exit than he did.

You see, Townsend sees that the first million of revenue can seem impossible. That the second million can make the plan seem workable.

But then, you have to start thinking differently. You have to start building a team that can scale what you simply can’t do on your own.

On the other side of that is magic.

Townsend is creating a community for founders who are, in his words, “crazy enough to start something.”

It could include you. And you would get access to a group of people who have been at every step of that founder journey — start-up to sale and beyond.

Let me know and I can arrange an introduction.