Six lessons from a bootstrapping startup founder (part I)

The failure rate of startups is high – alarmingly high. Some estimate that 9 out of 10 startups will eventually shutter. So the fact that my company, Small Improvements, is still here and thriving after six years means I get a lot of people asking how we found the secret to startup survival.

I’ll be honest: the first two years were a combination of focus and luck. Then the problems started mounting. I’ll admit I made my share of mistakes on everything from scaling the team to employer branding to personal check-ins. I love this company and I’m proud of how successful we are now – but there were times when it was close to just fizzling out.

As we celebrate our six-year birthday in 2017, I wanted to reflect on the many successes we’ve enjoyed as a team. But I felt it was also important to be mindful of the lessons I’ve learned over that time.

Over the course of two blog entries, I’ll categorize the six biggest takeaways I’ve gleaned as a bootstrapping founder.

No. 1: Sales doesn’t have to destroy the company’s soul

I come from a developer background and had never worked with sales teams directly. I had a misconception about how a sales process works, thinking that anything beyond pure basics requires selling your (or the company’s) soul.

Summer Part 2017 – beers and warm weather on the Spree River in Berlin

While I loved listening and reading how others experimented with their quotas and processes, I was always intimidated by these overwhelming formulas, the pressure one supposedly needs to exert, the risks associated with sales staff over-promising, the high bonus payments required to get the best of the best, etc.

In hindsight, reading all these horror stories influenced me far too much. I postponed the entire sales process setup, and that was a major mistake.

I should have set up a sales system three years ago. But I was simply too influenced by those I spoke to and what I was reading. Ultimately it turned out that getting this process off the ground was simple. We hired smart people and gave them the freedom to set up their own processes. Most crucially, they’re motivated by working for a nice company that makes a quality product, rather than money.

No. 2: Employer branding is a lot harder than I thought

Hiring developers was hard, and hiring a project manager was almost impossible. I feel we’ve always had better-than-average careers pages, we’ve always blogged, and our transparency and our events are strong. But better than average is simply not enough: our bar for candidates is high, and I have to blame it on myself for not emphasizing employer branding.

We’re now playing catch-up: Each developer team has their own page on the website, we’re blogging more than ever, we’re open-sourcing some really advanced work, and we’re starting to share a lot more about our internal workings publicly (e.g. with applicants).

Employer branding plays a crucial role in related areas, too – our current website and blog overhaul projects are largely driven by branding needs as opposed to customer acquisition needs.

And despite all the progress, we’re still far from perfect. The main challenge is that there’s just so much to do. I didn’t expect potential employees to have such high expectations.

Looking back, I was concerned a bit too much with product progress and should have spent more time on public-facing content. The product is also important, but if only the product steams ahead while the website looks frozen in 2014, then don’t be shocked when you struggle to attract new staff and customers alike.

No. 3: Build up marketing and product management much earlier

Building a technical product, I knew we needed a strong developer team. One doesn’t build a complex SAAS solution with just three developers. But I erred on the side of asking developers to be overly “product-y” and didn’t hire enough into marketing and sales and project management to help them. By asking developers to do a little of everything, they ended up coding less – much to their disapproval.

Pizzas for the team during the Nov. 2016 Ship-It Week

True, some of our very early hires included a marketing director and two customer support staff. But as we grew the development team, I forgot to grow marketing accordingly. On top of that, we didn’t invest into sales side. And I realized far too late I couldn’t keep up with product management for the eight highly productive developers I hired over the first two years.

And when I finally realized, catching up proved really hard. For instance, it took us 18 months from deciding “we need a PM,” to her actually being found, hired and onboarded.

While it’s enjoyable as a developer to be involved, it’s hard to be spread so thin. Nobody here wants to be only a “code monkey” but that doesn’t mean all developers enjoy writing release posts or editing release tweets. Or doing their own product management.

Once we brought on board more marketing staff – even though they themselves were just learning the ropes – developers sighed with relief. The same is now happening with product management, and we’ve really upped our game on sales.

For the next three lessons about what I’ve learned in six years, check back in August.

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