Five Crucial Things I Only Could’ve Learned By Scaling My Startup

Buffer COO Leo Widrich shares what he’s figured out in the course of growing the company to reach $10 million in annual revenue.

Five Crucial Things I Only Could’ve Learned By Scaling My Startup
[Photo: Flickr user Steve Jurvetson]

In five and a half years of Buffer, we’ve been fortunate to cross many milestones–3 million registered users, 90+ team members, and most recently, $10 million in annual recurring revenue. Some of the lessons we learned to help get us there came easily. Others we learned the hard way. Here are some of the most important things we’ve figured out how to do.


1. Have A Weekly “Mastermind” Session With Your Cofounder

Investing in the relationship between my cofounder, Joel, and myself–on top of the work we are already doing on the startup–has been extremely rewarding and useful. When I talk to other founders about this, they sometimes tell me, “We’re already spending so much time together as cofounders, we know everything!”

I found this a quite easy trap to fall into, and I’ve thought this myself once in a while. But I firmly believe our weekly “mastermind” sessions have helped us solve so many more problems that we wouldn’t have otherwise. Here’s a quick look at how we’ve set up our weekly masterminds:

  • We take around 1-2 hours, preferably when it feels a bit less busy. Joel and I typically meet on a Friday.
  • We talk for 10 minutes each about our achievements. These can be things like “I shipped this feature” or “I hit the gym 3 times this week.” As entrepreneurs, we often don’t celebrate our achievements enough and that can lead to burnout. Taking just a bit of time to think what is going great, even though there’s so much more to do, can be so valuable.
  • We spend 40 minutes each on challenges. We try to really dive in and not stay on the surface. One consideration I’ve found helpful here is to avoid trying to solve each other’s problems, instead simply listening.
  • At the end, we share feedback for each other. This helps ensure that things that might be bothering you don’t build up.

2. Avoid Being Distracted By Data Too Early On

We live in a time where data is all around us, and there’s a lot of great advice to show us how to make better use it. However, I’ve found that in some cases this can be a huge waste of time, especially early on.


I love this quote from one of our mentors, Hiten Shah of KISSmetrics. He’s a guy who sells analytics and data software, so if he advocates that you don’t do that, I find that doubly encouraging:

Most early stage startups won’t have enough customers to rely on quantitative data. You need to be acquiring hundreds of customers every month (preferably thousands) to have enough data to support A/B tests, etc.

Replace some of your current focus on quantitative data with qualitative data (for example, a number of face-to-face discussions with your customers).

3. Ask These Five Questions To Learn Better From Customers

Talking to customers and learning to do it well is something I’ve found to be extremely difficult in practice. It’s taken us a long time at Buffer to get a good process in place.


Here’s a simple way to immediately learn a lot from your customers with just five simple questions. These come from a book called Lean Customer Development by Cindy Alvarez, and I highly recommend it.

  1. Tell me about how you do _________ today.
  2. Do you use any [tools/products/apps/tricks] to help you get ________ done?
  3. If you could wave a magic wand and be able to do anything that you can’t do today, what would it be? Don’t worry about whether it’s possible, just anything.
  4. Last time you did ___________, what were you doing right before you got started? Once you finished, what did you do afterward?
  5. Is there anything else about _________ that I should have asked?

We use these five questions on a daily basis to make sure we’re learning valuable insights from customers. The real key here is that you won’t see any leading questions. It’s important that there are no “Would you like it if…?” or “Would you use this…?” that could bias or influence a customer’s answer.

The “magic wand” question is one of my favorites. Everyone likes to be a magician. It can feel a bit out of place to ask that question sometimes, but I found it can jumpstart your customer’s creativity and perhaps even take the discussion in new directions.


4. Seek Conflicting Advice From At Least Two Mentors

This has been a particularly important lesson, especially when it comes it our biggest decisions. Personally, the way I operate is quite opposite from this. I hear some advice from someone, and I’m hooked. I want to go ahead and do that thing immediately.

But this can be counterproductive to finding your own way and building an authentic business. After all, there are a lot of big decisions to make:

  • Should you fundraise now and how much?
  • Should you build that new product?
  • Should you hire that person for that role?

For each decision, speak with someone that has one opinion and then immediately seek someone else’s opinion where you know he or she might think differently. You might be surprised by the varying perspectives and the ideas that might form.


5. When You Get An Offer To Sell, List The Growth Experiences You Might Miss

At Buffer we’ve had four serious offers over the past five years. Not one of them was easy to work through. When you consider an offer, make a list of the experiences you’re possibly leaving on the table if you sell.

We often think about how much money we could make now with selling, versus how much money we might make in the future. But sometimes, thinking about personal growth in both scenarios can be a more powerful indicator.

These are some of the things we would’ve missed out on learning if we sold:

  • How to serve tens of thousands of customers
  • How to hire key positions and train leaders
  • How to raise bigger funding rounds
  • How to recover from a hack
  • How to let someone go

At Buffer, we often talk about wanting to be a person of value, where we can offer advice to others and be useful. This is often only possible if you’ve had a lot of these experiences.

An expanded version of this article originally appeared on Buffer. It is adapted and reprinted with permission.