This is a post in a blog series on "things we learned while bootstrapping from 0 to $10M in ARR". Follow me on Linkedin for new posts.

The notepad I mentioned in my last post contains a rather wild collection of “things we learned while bootstrapping”, jotted down during a long flight a couple of weeks ago. Some are rather practical or even technical insights, some focus more on strategy and some on team dynamics.

There was no particular order to these (side effect of writing in a dimly lit cabin while the person sitting in front of me maxed out their full seat inclination freedom) but I decided to start with a post on team dynamics.

Why? Posts touting how “ChatGPT built my company in 7 days” proliferate on Linkedin these days, and yet building a business is still a quintessentially human endeavour. And building a business in a capital-efficient way means the foundation of your business - the relationship with your co-founder - has to work fairly efficiently, too.

“Efficient” is probably not the attribute that first comes to mind when you think of “great relationship”, but I will gladly feed the German stereotype (and obviously I would also describe our relationship as “fantastic” - but that’s not the point of this post).

In a resource-constraint setup you have to focus all your energy on being productive with the very small team you have (initially it will just be you, the founders). You simply don’t have time for friction and expansive interpersonal issues.

So here’s a non-exhaustive list of things that helped us build a solid foundation:

Codifying founder values and responsibilities

While the urge to simply jump right in, start coding and pitching felt great, we sat down with a cup of steaming tea on a dark and grey Berlin autumn afternoon in November, opened a Google Doc and wrote down a couple of things:

• Why we were starting this company: This was pretty obvious to us, we had always sought out impact-oriented jobs, both felt the pain of underinvestment into people enablement in our previous jobs and wanted to make work more meaningful;
• How we wanted to work together and what was important to us: We wrote a short “manifesto” on things like always putting the company first, not giving in to our egos, being radically transparent with each other, etc.
• What - based on the the strengths that we saw in each other- our areas of responsibility would be: Jenny would focus on Sales, People and Ops, I would focus on Product, Marketing and Customer Success.
• How we would split ownership of the company (50:50) and how we would resolve potential decision impasses because of this ownership split (which are far more frequently mentioned in startup literature than they actually occur, so this was - in hindsight - a rather theoretical issue).

The advice is this: Ask these questions early on and write down the answers. Some of these questions might be hard. They are. Don’t postpone them and let them linger. Especially if you don’t know each other well, they will distract you. You will be more focused and more at ease if you get them out of the way quickly. Some questions might also seem a bit fluffy. They are not. They help you create a foundation that you can refer back to as you start giving feedback.

Giving each other regular feedback

In the first year or so, Jenny and I had regular feedback meetings that were a dedicated “safe space” to speak very freely about everything that went well, but also vent about everything that didn’t. We still do this today, but somewhat less frequently.

Especially if you haven’t worked with each other before, the early days of co-founding a startup can be bumpy.

Despite everything that’s going on in the early days, make time for regular feedback - 30 minutes every two weeks. This will be hard at first, but it becomes easier over time. I had (and probably still have remnants of) a tendency of communicating very concisely (or less euphemistically: not providing enough context) and am very grateful that Jenny flagged this early.

By doing this, you ease potential tensions early on, you become better at working together, you learn something new about yourself frequently, and as a result of that, you personally grow faster. If you are just getting started, you probably don’t need it yet, but once the team is growing a bit, we’d obviously love to show you Leapsome.

Running weekly founder check-ins and monthly strategy syncs

Reserve an hour every week to discuss operational topics and meticulously prepare for this (we built this tool into our platform and it’s my favourite feature).

Separate strategic check-ins from these operational discussions - you need more time to really dig deep and should proactively take that time about once a month. Decide up-front what you want to discuss, focus on one or two topics per 4-hour session and try to resolve them in one go.

Celebrating together

We’ve admittedly always struggled with this, but have at least become much better over time. Building a company is hard work and it’s just so much more fun if you celebrate the important milestones.

When you win a customer, ship a new feature, finally close that person you really wanted to hire, instead of carrying on right away, take time for that high five (or Leapsome praise!), and maybe even have a drink to celebrate.

Being incredibly lucky

I’m closing with the most difficult point, as other than fostering your network, there is not much actionable advice here. Meeting the right co-founder at the right time is probably one of the most serendipitous elements of a startup journey. If you are using the right lens, you realize you are fishing in a very small and shallow pond rather quickly. At the end of the day, you are looking for someone that ideally

• has a highly complementary skillset (unless you have tons of spare money to hire whichever people with skills you don’t have in the founder team)
• shares the passion for the topic or idea you want to explore and can discuss strategy at eye level (you need a sparring partner for the difficult choices)
• shares your risk affinity not just in general, but at the same point in time when you are ready to make that scary jump

This requires luck. Jenny and I had randomly met ten years prior to starting Leapsome, had stayed in touch over the years (living in the same city helped) and were both inclined to take new risks at a similar time.

Just like any relationship, a successful co-founder relationship requires hard work and continuous investment. It pays off, through increased focus and efficiency from the early days onwards, and by providing a role model for other relationships in the organization later on.

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