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The Entrepreneur’s new path of maximum optionality

“Bootstrap a lifestyle business, strap yourself in to the VC roller coaster, or take out a loan with a personal guarantee and risk losing everything if the business fails.”… For as long as I have been an entrepreneur this was pretty much the menu of options available to most founders of software companies. Before you even tested the business you had to commit to one path and hope you chose wisely. Choose incorrectly and you could kill an otherwise great idea by setting yourself down the wrong path. Raise VC for a business that tops out at $10m a year in revenue; you’re headed for zombie status or a forced acquihire. Carefully build a small profitable business; well you’re obviously not the kind of ambitious dent-in-the-universe founder VCs want to back, so get ready to burn through your savings. Good luck even getting your local bank to talk to you about a loan to start your new SaaS business; you’d be better off asking them to finance the 5th Taco Bell in town.

But recently, a proliferation of new tools and funding options are creating more pathways for entrepreneurs to build and fund software companies while maintaining flexibility and optionality. Let’s follow the path.

0/?You find a unique pain point and have an idea for a product that will solve it

What you don’t do is put together a pitch deck, finagle a multi-billion-dollar total addressable market and spend the next 6 months fundraising. You know that for all the new “pre-seed” funds popping up and all the talk about how “it’s never been easier to raise money” that fundraising on a pitch deck and an idea is a long, hard, time-consuming process that’s unlikely to be successful. Better to just get started on the business without asking investors’ permission. So you do…

1/?‍♀️Launch a minimum viable product and get your first customers

The path starts by just getting started. You work directly with your potential customers and validate that they actually have a problem and want to pay to solve it. Here your options have never been better.

  • You could start a consulting business first. Spin up a simple LLC with Stripe Atlas and use recurring invoicing tools like Harvest or Freshbooks and you have yourself a side-hustle consulting business. From there you can test if there is true willingness to pay in this market and learn more about what kind of product your customers would pay for.
  • Use no-code tools to stitch together a prototype of your product. You could use Makerpad to find the right combination of tools that let you build a software product without code. This could either be a duct taped version that actually does what it says on the label, or a “Wizard of Oz” version that looks and feels like software, but actually you are doing the heavy lifting by hand behind the scenes.
  • You could learn enough code to build the first version. Depending on your learning style, budget, and time, you might prefer coding bootcamps or online tutorial repositories (like Pluralsight or Egghead) or both. Starting with a product to build is the best way I know to stay motivated while learning to code. Even if the product fails, you will have learned a valuable skill.
  • You launch your MVP and get your first customers.

2/?$2-5k MRR (monthly recurring revenue): “rent money” and growing

Your product is live, people are paying for it. Those people stick around (retention) and more people continue signing up (growth). You’re in business now. Once you get to a few $1,000 in monthly revenue, “rent money” level, you have several options on how to proceed.

  • Continue to bootstrap the business on the side. If you can continue to balance a job or freelance work, you can run your business on the side and keep it growing until it generates a full-time income for you.
  • You could go “digital nomad” and move somewhere like Thailand, Bali or Budapest, with a very low cost of living and where your new product can support you full-time. This isn’t an option for many people with a mortgage or family to take care of, but for the right entrepreneur it can be a great way to cut your personal burn rate and keep your options open.
  • With this traction you could raise $50k-150k on a Shared Earnings Agreement (or SEAL) which would allow you to go full-time 1 on your business. A SEAL is designed to bring on investors who will back you early on and let you decide later whether you want to build a profitable sustainable business or a high-growth rocketship.
  • At this point you would likely have a great shot at joining your accelerator of choice. But know that most accelerators’ business model is predicated on getting as much of their cohort funded by VCs as possible. If pivoting the business to larger markets, focusing on short-term growth, and honing your pitch to maximize your raise on demo day isn’t what you want, either skip the accelerators or be very clear upfront that you aren’t sure you want to go down the VC path… yet or ever.

3/ ?$5-25k MRR: ramen profitable + team

You choose a path that gets you working on the business full-time. You start to get initial product-market-fit and feel like your product really solves a genuine pain point. You find a few channels of organic (ie free) growth and begin hiring your first team members. This gets you to “ramen profitable” where you can pay the founders a reasonable salary, at least to where you aren’t burning through your savings or the capital you raised. So what will you do to power the next phase of growth?

  • As always, you can stay bootstrapped, grow organically, hire slowly, and run a Calm Company. This is particularly good path if you have a product with high retention, good free sources of new customers, and you are focused on a niche without too many direct competitors.
  • But maybe you want to make a few key hires—a top tier marketer, the first person in outside sales, or a senior engineer to take the product to the next level—that current cashflow can’t support yet. New funds like Indie.vc and Earnest Capital 2 are ready to back companies at this stage that want to stay focused on building real, profitable, sustainable businesses. You could raise $100k-$500k to see if you can meaningfully change the growth of the business while still planning to return to profitability.
  • You might run some growth experiments, either with your own cashflow or the capital you raised from Earnest or Indie, and discover that there are a ton of ways to turn cash into growth for your business. Now might be a great time to raise a few million in a Seed / Series A venture round on much better terms than before you had this traction.

4/ ?$25- 100k MRR: maximum optionality

You continue growing the business with several proven channels for customer acquisition. You have a minimum awesome team in place that can ensure the product is the best in its class. Somewhere in here you hit or have line of sight to a $1m/year business with a diversified customer base and likely some nice profits. If you’ve gotten here without taking too much outside capital, you have navigated the path to maximum optionality because the number of options for taking your business from here are numerous. You could:

  • Keep funding your business with the most optimally formulated fuel that keeps you absolutely focused on building the best product you can: customer revenue.
  • Somewhere in this range, the traditional banking system3 will finally become helpful. You’ll be able to fairly easily access a $100k line of credit or $50k+ in credit card limits to alleviate any short-term cashflow constraints.
  • You may still want to bring on some more long-term aligned investors for a mix of patient capital, mentorship, and network. In which case the funds from #3 are still a good option, but you could also probably do a large enough raise that a priced equity round might make sense.
  • A huge array of specialized revenue-based financing lenders are now interested in your company. Folks like Lighter Capital, SaaS Capital, Bigfoot Capital, TIMIA Capital, and RevUp will lend upfront capital in exchange for a percentage of your monthly revenue. Unlike traditional banks, these funds do not require a personal guarantee. They are debt instruments and typically become really viable around $50k MRR when the business has become fairly proven and predictable.
  • You might also find that your business has a few “money machines” where you can plug money in and get more money out. Specialized funds like Clearbanc, which will finance your paid marketing budget (ie Facebook or Google ads), or Braavo, which will finance your receivables from app stores, are available.
  • ☝️All the options to this point are not mutually exclusive and can be layered on one another in whatever way makes the most sense for your business.
  • But also, at this point you could likely sell your business for a life-changing amount of money. You’ve kept most or all of the equity in the business. You likely don’t have a board that can block a sale or giant liquidation preferences that make a sale for a few million unattractive. Even if you don’t sell, knowing that you could at any time is a powerful source of freedom.
  • Or, you could look at your $1m/year business and realize at this point you are in or adjacent to a $1B market. You are a proven founder. Your product, sales, support teams are well-oiled and scaleable. You talk it over with the team and decide to shove all your chips in and raise a monster round of VC on far more attractive terms than you could have at the beginning of this process. You could, but you absolutely do not have to.

5/ ?To Rocket or Not

The beauty of all of these options is that most of them can be mixed and matched. Entrepreneurs now have far more choices and paths that allow them to test the market, grow their business and move forward with or without funding. The choice is up to you.

This is the entrepreneurs new path of maximum optionality.

  1. Disclosure: I am the founder of Earnest Capital, which created the Shared Earnings Agreement↩

  2. Again, full disclosure, I run Earnest Capital.↩

  3. at least in the US↩

We need a new default funding model for tech companies

There is definitively a small but growing trend of new forms of financing for early/mid-stage tech companies. As a founder and bootstrapper, I feel like I saw the opportunity before I understood why it was there. I wanted to lay out the simple macro framework for why I believe this is just the beginning of a huge shift in how we fund startups.

Premise 1: Almost all new companies are technology companies now

Anil Dash and many others argue that there is no “technology industry” and that the label is too big to be useful.

Almost all companies use tech in some way, just like almost all companies use electricity.

Premise 2: Most companies (tech or not) are not a fit for VC and don’t have alternative options.

And yet there is this totally out-sized relationship between tech companies, which most new companies are, and venture capital, which is definitionally not a fit for the vast majority of companies. So every founder building in software/web/tech thinks they should raise VC when in reality almost none of them should.

But what should they raise? What about debt.

My father took out a loan in the 70s to start his business. That’s how most of the small business entrepreneurs from that era got started. You took out a loan, bought property and equipment, started your business and if you failed the bank foreclosed on your building and equipment, and depending on the loan, maybe your house and personal assets. Seems pretty risky to me but at least it was a well-known pathway to capital for entrepreneurs starting new ventures.

The problem is most tech companies don’t have collateral and you simply can’t get a loan at the earliest stages.

We’ve seen a precipitous drop in new firm startup rates since the early 2000’s. I don’t think my theory here is fully explanatory, but I think part of the problem is the fact that there is no good default financing option for entrepreneurs.

Why it’s all happening now

How did we end up in this position? Jerry Neumann, argues persuasively in this post that we are now in the Deployment Age of the internet/web/mobile technology cycle. This is an application of Carlota Perez’s theories in Technological Revolutions and Financial Capital. This podcast is excellent and compelling that we are past the age of bubbles, crashes, and winner-take-all opportunities specifically in the internet/web/mobile sector. We now get to deploy all the new productivity gains of the web to a ton of new sectors in a much lower risk way.

 

During this phase, new kinds of capital are needed with a different risk-return profile. The easiest comparison for me to wrap my head around is this quote from the post describing the creation of tons of new forms of consumer credit starting in the 20s.

Venture capital, as we think of it, is primarily a feature of the current cycle. Other cycles had other funding mechanisms. E.g.:
The consumer boom of the 1920s was financed through a vast expansion of credit, with personal debt nearly doubling as a proportion of income. And since banks did not make consumer loans, new lending channels had to be created. These included installment sales finance companies (such as the General Motors Finance Company founded in 1919), retail installment lenders (particularly department stores), licensed consumer finance companies (such as the Beneficial Loan Company) and Morris Plan industrial banks4.

 

This is just the beginning

Thus we find ourselves in a moment when there is vast demand to fundamentally re-define the default form of capital for entrepreneurs. It’s an exciting opportunity and a great time to be both an investor and a founder in this space.

How I email

In 2019 I’m transitioning into the role of an investor at Earnest Capital. Since we soft-launched in October with a call to collaboratively build investment terms for “funding for bootstrappers” I have received 100x the normal volume of emails that I’m used to processing. Looking forward it seems clear that being an investor in early-stage startups means becoming a professional emailer. As I’ll be spending most of my day in email1, I thought it would be a good idea to explicitly state my email preferences somewhere I can link to.

This should simply be viewed as a list of my preferences, not some list of demands that must be complied with in order to email me2.

Things I think about email

  1. Many VCs seem to view responsiveness as a competitive advantage, replying near-instantly at all hours. I’m not sure that’s a factor I want to optimize for but even if it were, I know I would never be an exceptionally fast responder. So I’m not going to compete on responsiveness. If you’re used to dealing with VCs and getting instant responses, emailing Earnest might seem jarringly slow but I’m okay with that.
  2. I optimize for completeness in a response. I prefer not to trade 25 half-baked emails back and forth when I could wait for all the facts I need and write a detailed, clear, complete response.
  3. I am remote-first and I prefer emails as the default mode of communication. Switching to scheduling a call the moment an issue becomes complex is a habit I don’t share. Let’s be thoughtful, clarify our thoughts in writing, and use a call as a last resort (or just something that’s fun but not necessary).
  4. I don’t do Inbox Zero. I used to, but feel that I frequently need more time for responses to marinate than an instant ‘respond, delay, delegate’ protocol allows.
  5. I do view my inbox as “other peoples’ todo list” and try to allocate my day first toward larger projects that will improve Earnest for everybody, then dive into my inbox.

My email preferences

  • I like long emails. I’m not one of those people who needs to get all the information in the first 3 sentences or I stop reading.
  • Follow-up as much as necessary. If I haven’t responded to your email, it doesn’t mean I won’t. I am most likely working on something else integral to a reply. Feel free to send additional follow-ups if there is new information. I prefer not to get a daily stream of “just bumping this to the top of your inbox”—though one or two is fine.
  • Please let me know explicitly if my default mode is not going to be appropriate. “I really need an answer on this by {datetime} because {reason}” is really helpful for me.
  • Don’t apologize. If we agree that sending me an email does not obligate me to send back an immediate response, there’s no need to apologize ✌️

Myers Briggs for Email?

We all spend so much of our lives writing and reading emails. Many people have radically different styles and preferences. I wish more people would explicitly write out their email preferences. Eventually, we’ll categorize and group them into themes like a Myers Briggs for email. So just as you can short-hand with “I’m an INTJ” and confer a lot of information on how you prefer to interact, you can say “I prefer my email as Correspondence” or “I’m an aggressive Inbox Zero-er” and confer a lot of the preferences above. I view my email preferences as Correspondence in reference to how people used to communicate when hand-delivered letters might take months to be delivered by ship. You had to be thoughtful and clear and close as many open loops as possible.

  1. I’m using Superhuman these days as I write this.↩

  2.  hat tip to @devonzuegel for the inspiration for this↩

Selling My Bootstrapped SaaS Business

Five years ago I built and launched the first version of a SaaS app on a single flight from San Francisco to Buenos Aires. Slowly and steadily, Storemapper grew into a healthy location-independent business for one person and then later a small dedicated remote team. At parties, I would describe it as, “not a startup; a healthy growing internet small business.” This year, almost exactly five years after launching, I sold the business for what, to someone growing up middle class in Florida, is a life-changing amount of money that will enable all kinds of exciting new projects and adventures. From start to finish, it has been an exciting ride, much of which I have documented here on the blog. With the sale concluded, I wanted to share as much as I could about the process of building a business that can be sold and how I sold it.

There’s always a risk that these posts turn into a 5,000-word humblebrag. But I really do think it’s worth a read because, unlike most business acquisition stories, which often feel like an out of the blue stroke of good luck, the way that I sold Storemapper feels very replicable for other entrepreneurs. When I spoke to someone two years ago about what it would look like if I ever sold the business I would say, “I’m not trying to sell it now, but if I ever did it would probably look this…” And six months ago I would tell a few folks privately, “I think that one of the people I met recently might be the one to buy Storemapper and if they do it will probably go like this…” And, then basically when it all went down it looked more or less like… that. There wasn’t some single huge stroke of good luck, though of course, I got lucky in the little ways that every successful business has to. An excellent outcome, but also a perfectly reasonable and achievable one that I think can serve as something of a template for other bootstrapped entrepreneurs.

This is a long and detailed post. I had so many questions going into this process and I didn’t find a ton of good posts from the founders perspective on selling bootstrapped businesses. So I thought I would just throw everything I could think of into a post and let you skip around or save it for reference when you’re considering selling your own business. Grab a pot of coffee and let’s get started.

First the obvious: why sell your software business?

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