The Other Side of the Exit: Greg Head on New Ways of Building a Software Company

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.

#founder #saas #softwareunicorn #exit