Why I Started Boundless

First, Thank You Alpine

After 15 wonderful, challenging, and rewarding years, December 31st, 2020 marked my last day with Alpine Investors. While I cannot claim I knew what I was doing in my early years, I was the willing (and grateful) guinea pig for many Alpine “firsts.”

I began as an Alpine summer intern in 2005, then became the first full time analyst in 2006 (when the mere 10 of us could stay in one home for our offsites). In 2014, I was fortunate to become the first CEO-in-Training (“CIT” -- there are now over 50!), was the first CIT to become a CEO, and the first to lead an Alpine business to exit. I’ve served in full time roles with five different Alpine companies, from Biz Dev Manager to Head of Product to CEO.

I hold so many of the Alpine values and principles dear to my heart, and I owe a great debt of gratitude to the Alpine partners and the broader ecosystem for supporting me on my journey. I am a proud alum and look forward to a lifelong relationship with the firm. I will forever bleed Alpine blue.

Why I Started Boundless

Boundless is a venture studio that builds industry-specific SaaS companies from scratch. We focus on niche services markets with acute pain points that could use better software to be more efficient and, in turn, to better serve their customers.?

Unlike a VC firm, Boundless ideates and builds its own companies, as opposed to investing in other people’s startups. We are structured as a holding company, not a fund, launching sub-companies underneath the Boundless umbrella. We hire a diverse array of aspiring entrepreneurs to build and lead our companies. We provide active mentorship, coaching, community, and technology leadership. And we empower these extraordinary leaders with our dedicated network of engineers, designers, and growth marketers to help them win. We handle HR, legal, finance, and all the back office functions to help them focus on building great businesses. Our goal is to launch 100 companies over the next 10 years.??

There are five main factors that have led me to launch Boundless.

Factor #1: Bootstrapping is alive and well, despite the VC narrative in the media about “blitzscaling.”

Traditional venture capital serves a very important purpose in stimulating innovation and building the next generation of Fortune 500 companies. Many companies need substantial capital to build a substantial business, and aim to do so as quickly as possible.?

If you read TechCrunch, VC blogs, and other sources of startup news, there’s not a lot of love given to bootstrapping. It’s unsexy. The narrative is around “blitzscaling,” raising and burning through tens of millions of dollars, striving to be the next $20 billion IPO. If you’re not the next Slack or Facebook, you’re not interesting.?

For the last 2.5 years, I have served as President of ASG, a vertical SaaS holding company that has acquired over 30 companies. Twenty-seven of them were bootstrapped almost entirely by the founders. And these are great, profitable, growing companies. When you focus on distinct niches and treat the operating expenses like your own cash – which is easier to do when it actually is! – it’s amazing what you can accomplish.?

I’ve lived through dozens of exits now, and know plenty of scrappy bootstrapped founders who became decamillionaires through achievable exits. They didn’t build the next unicorn -- they were hyper equity efficient and built thriving, enduring companies.

Bootstrapping is the ethos we espouse at Boundless.

Factor #2: Recurring revenue coupled with niche vertical SaaS is a powerful combination.

Prior to ASG, I ran a consumer business -- YouCaring. It was an amazing, social-good crowdfunding company that we grew from 3 to over 50 people (and revenue and EBITDA along with it) before selling to GoFundMe. We also operated in a market that forced us to rebuild our customer base every day, as old fundraisers tapered off and new ones started.?

With mission critical SaaS that targets specific industries, and a predominantly recurring revenue model, you can build incredibly sticky and valuable companies that experience a compounding effect as they grow. And while you often serve a smaller addressable market when you target one specific industry, you also disproportionately shrink your list of competitors, you can tailor your required feature set to be exactly what the customers need, and you can refine your go-to-market strategy in ways that tee you up for hyper-efficient growth. Focus is a force multiplier, a magical compounder. And thus, we believe industry-specific software will continue to be a winning strategy.

Factor #3: There is $1.5 trillion of private equity dry powder out there.

From 2000 through 2020, the private equity market has gone from just under $300 billion in “dry powder” (idle cash, ready to be invested), to nearly $1.5 trillion. The number of firms chasing deals has more than doubled as well in the past decade. The buyout world is increasingly competitive, and buyers are swimming farther downstream to acquire smaller and smaller companies. Thus a rich buyer universe exists for growing and profitable SaaS companies. If you can build a solid business, it is going to be a builder’s and seller’s market for years to come.

Factor #4: There’s a massive talent pool of “missed opportunity entrepreneurs.”

An example I love on this point is that at Stanford’s Graduate School of Business, roughly 40% of students come in saying they want to be an entrepreneur, yet only 10% actually start a company upon graduating. Why is that? It comes down to five key obstacles:

1. They don’t have “the idea”
2. They can’t afford to take a massive pay cut
3. They don’t want to fundraise for 6+ months
4. They fear failure
5. They fear being an island and missing the camaraderie of a cohort

Boundless is the antidote to these obstacles. We have a proven system for ideating internally, vetting those ideas, and bringing them to life. We have committed capital. We partner with dedicated leaders who want to co-found these businesses with us. Much more to come on this. If this gets you fired up, ping us at [email protected].

Factor #5: The personal one... I simply miss building, I miss creating, and I want to fulfill my professional dream of founding an enterprise that can outlive me.

ASG was an incredible personal experience for me, working with awesome founders, CEOs, a winning team and culture, and a strategy that will continue to yield outsized returns for years to come. After traveling through ASG, I found myself wanting to be earlier stage, to move from building companies post-acquisition -- and much later in their lifecycle -- to the very hardest part of business, which is taking an idea and actually turning it into something.?

I get to breathe life into a new business model, recruit and work with wildly talented leaders, address real pain points in overlooked industries, innovate rapidly, and do so at scale across dozens of companies over time. This will be hard, we will fail plenty, we will have bad days, months, and likely years, but that’s what I’m signing up for.

Above all, the most important factor in one's success is who you surround yourself with. I feel incredibly fortunate and proud to work with my co-founder and President, Khalil Fuller; our brilliant CTO, Sang Venkatraman; and our brave first CEO, Kyle Clements. I love embarking on this adventure with you all.

Thank you to everyone who has supported us on this journey so far. We are grateful to have investors and advisors like Mark Strauch, Partner at Alpine Investors; Dave Glazer, CFO at Palantir; Freddy Kerrest, Executive Vice Chairman, Chief Operating Officer, and Co-Founder of Okta; Suzanne McKechnie Klahr, founder and former CEO of BUILD.org; Jesse Wedler, Partner at Capital G; and many more. For Boundless to work, we’ll need to stand on the shoulders of giants, and we couldn’t ask for better giants. So thank you for your time, generosity, and support.

And now, back to building.

To our Boundless future,

Dan