Bootstrapping vs VC – a Founder’s Comparison

How does a bootstrapped exit compare to a VC exit, from a founder’s perspective?

TL;DR A VC-backed company will have to exit for 4-10x the valuation of a bootstrapped company, if the founders are to have an equivalent payout.

The above infographic (click to see the full version) does an excellent job illustrating the general stages of the startup company life cycle, except that most end in failure or acquisition rather than IPO. The percentages on the original graphic are dated and I’ve updated them above. The general point remains – each capital raise reduces founder equity in return for powering future growth. But the actual math matters – let’s take a look at some sharper numbers:

  • A typical VC-backed startup goes through four rounds prior to exit, where founders’ equity is reduced by 15, 25, 25, and 25%, with another 5 points lost to the options pool shuffle, advisors, board members, and other hangers-on. The four rounds are the seed round, Series A, B, and C.
  • The options pool shuffle is a clever trick VCs employ to capture a bit more equity. Advisors and board members often command 0.5 to 1% of the company each as well.
  • The compound impact of this at exit: founders’ + employees’ equity at exit totals 30% (a range of 20-40%). If we assume 2% in exit transaction fees and 8% fully diluted to employees, that’s 20% to the founders at exit.
  • Using the same assumptions, a 100% bootstrapped company has only the final 10% in exit transaction fees and employee compensation, leaving 90% to the founders.
  • The math above is daunting: 90% vs 20%! This tells us that founders should go the traditional VC route if they believe that it will enable them to exit at least 4-5x larger than the size of a bootstrapped exit. I’ve validated these basic numbers in conversations with a number of founders, and while the particulars will vary, the general guidance holds. Many founders give up too much, and end up as low as 5% at exit.
  • This assumes that your company can get somewhere without funding, which may not be realistic.
  • Bootstrappers trade time for money to an extent, if growth is ever constrained by lack of funding.
  • When choosing whether (or how much) to raise, consider your total addressable market. If you’re in a profitable niche, bootstrapping may be optimal. If your TAM is greater than $10B, go raise money.
  • There’s an intermediate option – raise, but raise wisely. Bootstrap your MVP, raise after you’ve got something repeatable, and raise all you can that one time. If (and when) I do it again, I’ll strongly consider this option.

Here’s a sample of Real-Life Exits:

  • GrubHub founders Mike Evans and Matt Maloney each held about 2.6% of GRUB at IPO – this degree of dilution is unfortunately common.
  • At the other extreme, David Barrett owned 47.7% of Expensify at IPO – proving that with judicious use of capital, dilution doesn’t have to be extreme.
  • The founders of Toast (TOST) collectively owned about 17% of the company at IPO. This was worth $5.1B at IPO, but has fallen 70% since, with share lockups preventing a true exit.
  • Mailchimp was the king of bootstrapped startups, going from 0 to $12.3B at acquisition, and succeeding in a space while competing against startups equipped with $100M+ in funding. Had the Mailchimp founders’ ownership been similar to Toast, Mailchimp would have had to sell for $74B to net the same founder outcome!
  • Private exit data is harder to come by, but Riskalyze saw the founder and CEO holding roughly 16% at exit to private equity (this was not a complete exit, as the PE firm bought a majority stake but kept the team onboard).


Why HiddenLevers Never Raised Capital

When I started HiddenLevers and roped in my cofounder Raj in late 2009, we talked about what success looked like. We thought success would be running the company for a year and selling it for … two million. We thought we could demo our cool new portfolio stress testing technology to major brokerages and just have one of them snap it up! Naive – but also a comical underestimate of the value we could create.

It took us about a year to reach a semblance of product market fit, which occurred when we found the RIA space – independent financial advisors understood the value of using HiddenLevers for their end clients. Over the course of 2010 we had been researching addressable markets, and one thing I’m proud of is the quality of the TAM modeling we did at that time. A decade later it was still essentially accurate – we were in a highly profitable niche space, with several hundred million in total addressable market for the financial advisory space. Here’s the spreadsheet from September 2010 – row 12 is where the business ended up thriving.

We looked at that TAM and worked top down and bottom up – from the bottoms-up perspective, we set a make or break goal of 100 clients by July 4th 2011 or we would fail fast and shut down. From the top down perspective, I calculated – what kind of business value results from capturing one percent of this audience?

Looking at the business from both perspectives, a few things became clear:

  1. We were able to use trade shows, email marketing, adwords, and press coverage to grow profitably, and it wasn’t clear that investor capital solved a problem – we had free cash flow to reinvest.
  2. If we did raise capital, the scale of our addressable market damaged our chances of a successful founder exit – diluting your stake works if it’s in pursuit of a massive market, but poorly in a niche.
  3. Successful expansion outside our niche might require capital, but growth within it did not.

In 2020 we reached an inflection point – to sustain our growth, perhaps it was time to finally raise a round so that we could expand upmarket, build out an enterprise sales team, etc? It was this inflection point that caused us to reach out to the M+A market – the early growth phase of the company was complete, and we felt that it was better to join forces with a more mature organization than to try to build that organization ourselves.

For a business like HiddenLevers, bootstrapping fit perfectly. The math I outlined up top held up well, and it’s quite possible that taking capital would have actually hurt our exit outcome. But if I ever try to build something to conquer a big market (over $10B TAM), I’ll do it the “normal” way – with investors.

A Better Capital Gains Tax

Taxes on long-term capital gains have fluctuated in recent years, with rates as low as 0% (for lower income groups) and as high as 28%. At the end of 2010 capital gains rates will likely revert to 20% after being at 15% for several years. While long-term term capital gains enjoy a tax break, short term capital gains (on positions held less than one year) have long been taxed at marginal income tax rates. While dividends have more recently been accorded the same tax breaks as capital gains, interest payments continue to be taxed as marginal income.

Capital gains tax breaks are designed to encourage investors to invest in the economy for the long term, thereby promoting economic growth. As currently structured, the capital gains tax break doesn’t really achieve this, as it simply rewards investors that hold a position for more than one year. The law does not distinguish between investments in startups or IPOs and in purchases of existing equity shares. With regard to real estate, the law encourages the tax-free flipping of properties via 1031 transactions, but does not reward investors who improve their properties.

Rather than subsidizing investments in existing shares and property, shouldn’t capital gains tax breaks attempt to promote new investments? This could be easily accomplished by lowering the capital gains tax rate to 0% for all new capital investments, irrespective of investment duration. A new capital investment could be defined as an investment in which the target company directly receives the proceeds of the investment. Investments in IPOs, secondary offerings, startup companies (including angels and VCs), and real property improvements would qualify, while purchasing of existing shares and real estate would not.

A 0% tax rate on new investments would incentivize real investment in the economy, rather than encouraging simple tax-related shuffling of existing investments. In order to offset deficit impacts, traditional capital gains tax breaks could be reduced or eliminated. Moving to a system in which new investment is incentivized would tip American finance away from the casino mentality of recent years, and back towards its original purpose: investing in promising companies for profit.