How Long Should You Bootstrap?

With as little as it costs to get a software startup off the ground these days, many entrepreneurs start off as what we call “bootstrappers” rather than fundraisers.  There’s nothing wrong with that approach but staying in the bootstrapped mode for too long can carry some consequences.  This article explores that further.

What exactly is bootstrapping?

I don’t know what the dictionary says but, to me, bootstrapping is using existing or personally available resources to fund your venture.  In other words, not raising money from third parties.

  • Living off your savings account so you can work full-time on your startup venture is bootstrapping
  • Borrowing against your 401K retirement account to pay your bills while working full-time on your startup venture is not usually recommended, but is bootstrapping
  • Working on your startup venture during nights and weekends while maintaining another job to pay your bills is bootstrapping
  • Selling your car, leasing out your garage apartment and auctioning off the valuable comic book collection you’ve been holding for 10 years is bootstrapping
  • Secretly selling your spouse’s car and auctioning off their family heirloom paintings with sentimental value might cause a divorce, but is bootstrapping
  • Convincing others to work on your venture for no cash compensation while combining with any of the above options is bad ass ninja bootstrapping
  • Borrowing money or taking an equity investment from your friend, family member, bank or angel investor is not bootstrapping

OK, you get the idea.

Benefits of bootstrapping

Many of the successful entrepreneurs that I respect the most are consummate and repeat bootstrappers.  In fact, they take great pride in letting you know they’re a bootstrapper.  If you look, you’ll find them in your own community.

Before we talk about how long to bootstrap, let’s review some of the biggest benefits of bootstrapping.  Some of you will be able to skip the bootstrap phase altogether for one reason or another, and that’s great.  But you’ll miss out on at least some of the benefits listed below.

  1. No investors telling you what to do, giving you a hard time about the decisions you’re making or asking for a bunch of updates
  2. Hyper-focus on making rapid and sufficient progress to either be able to get funded and/or start bringing in revenue from product sales
  3. Detailed understanding of exactly where every dollar is being spent and it’s specific value to the mission
  4. Fosters maximum creativity, flexibility and instincts for survival
  5. Forces finding and attracting other team members that have genuine passion for the problem being solved (versus those looking for a paycheck)
  6. Many future investor prospects will be impressed by your passion and personal commitment to the venture as evidenced through your bootstrapping
  7. No dilution – you and your co-founders get to divvy up 100% of the equity

There’s a reason that I put the dilution benefit last.  Please don’t bootstrap just to avoid dilution.  If your business venture is best developed and grown by taking on early investment, you will be happier and richer if you do so.  One of my favorite sayings is “optimize for growth, not dilution”.  You would much rather have a single digit equity stake in a venture that eventually exits for $1B than double-digit equity in a venture that crashes and burns or exits for $2M, $10M or even $50M.

How long should you bootstrap?

To answer this question, I’m going to set aside ventures that are intended to organically reach a cash flow positive or profitable position and become sustainable on their own.  Instead, I want to talk about the more traditional tech startup scenario of pursuing multiple rounds of funding capital over time.

I usually recommend bootstrapping just long enough to gain sufficient evidence that your solution is Desirable, which means your target customer wants it bad enough that they’re willing to pay for it.  It’s also beneficial if you’re able to prove that the product you’re building is Feasible, which means that it can be built and can deliver the intended benefit.  That doesn’t mean you have a v1.0 product ready to launch but rather have enough proof that there’s minimal “technical risk”.

For additional reference, the graphic above shows the stages of the new business viability lifecycle.

With both desirability and feasibility validated (or mostly validated), you still have a long way to go before you’ve grown a great company that’s both scalable and sustainable, but you are considerably less risky than before desirability and feasibility were validated.  And that means you’re ready to pursue a pre-seed or seed round of funding.  There are dozens of reasons why you still might not be successful getting funded but that’s a topic for a different article (in fact, see “Having Trouble Raising Money?” and “Using Verbal Commits to Secure Your First Investors“).

To help with ideas for validating desirability, do some research into Design Thinking and search for a free video module I produced for my Founders Academy series called “Developing Your Idea” (it’s usually posted on the Home page or Videos page of this site).

Dangers of bootstrapping too long

From time to time I come across startups that have been in bootstrap mode for a seemingly long time.  You might be thinking that with all of the bootstrapping benefits I listed further above, why not stay in this mode as long as possible?  The most common issues with that approach are listed below:

  • Slow progress for too long – While in bootstrap mode your financial resources are limited enough that your progress is also limited.  If that goes on too long, you might be asked “How is it that you’ve been working on this for more than a year and only have ___ customers and ___ revenue?”  Investors like to connect many dots but when they connect yours over a long period of time the slope of the curve isn’t very interesting.
  • Mindset – The processes, culture and general mindset of bootstrappers is fairly different than those that are funded and swinging for the fence.  Staying in the bootstrap mode too long can cause the mindset to sink in to the point that investors are forced to wonder if you’ll be able to shift multiple gears directly into a fence-swinging mentality.
  • Assumptions – Investors can easily assume your business venture either went through a significant pivot, multiple pivots, a co-founder breakup, unsuccessful prior fundraising attempts, etc.  It’s even possible that some of these things are exactly true and caused the bootstrapping to last longer than intended but investors will often pile on additional negative or skeptical assumptions than whatever you choose to reveal.

Summary

As hopefully you’ve concluded, bootstrapping during the early days and until you’ve mostly demonstrated desirability and feasibility for your business venture can be a great thing.  But too much of a great thing can turn into a bad thing.

Compare notes with your co-founders and trusted advisors to have a general strategy and plan for your bootstrap phase.  And once you’re ready to take on seed investment, prepare for a change in mentality and get ready to go big.

Related Reading

Wait, there’s much more!!!

If you enjoyed this article, you’ll love what I cover in my video library called Founders Academy, which includes all of the key concepts and insights to help you dramatically increase your odds of success using topic-specific streaming video modules.  Click Here to Learn More

“Founders Academy is a must!  Gordon unlocked new value in concepts I thought I was already familiar with.” (startup founder)

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Author: Gordon Daugherty

Over the past 15 years Gordon has seen nearly 1,000 startup pitches, advised more than 200 entrepreneurs and been involved with raising over $45M in growth and venture capital. Throughout his 28 year career in high tech, serving twice as President and three times as CMO, Gordon has both an IPO and a $200M acquisition exit under his belt. Now his emphasis is purely focused on helping startups and early stage tech companies. Through his Shockwave Innovations advisory practice and as Managing Director for Austin’s Capital Factory startup accelerator, Gordon is an active angel investor, VC and startup advisor.

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