4 Painful Lessons I Had to Learn Again with My New Startup

A few months ago I started building a new product. It’s called Here and we’re building a community platform for meaningful and mindful connection. As I was contemplating it, I reached out to my long-term friend and mentor Hiten Shah. Hiten was the very first person that supported me when I began my startup journey. Almost exactly 10 years ago today I was building Buffer when I met him, as I stepped off the plane in San Francisco, wide-eyed and 21 years old.

As usual, this time around too, Hiten gave it to me straight, which I don’t like, but which I usually need. “You’ve gotten rusty now, rusty with the basics Leo…” is what’s still ringing in my ears. “You need to go back to square one, customer development, all that jazz, you know how to do it!”.

“Of course I know how to do it!” I thought exasperated, I’ve been teaching it to my clients as a coach and I’ve done it for years at my previous company!! But he was right of course. Teaching it and having done it years ago isn’t quite the same as knowing how to do it today.

So together with the lessons from the hundreds of coaching sessions over the last years and my own fresh learnings from the last few months I wanted to write this blog post to document what “the basics” mean to me and how I’ve approached them. I hope some of it is useful for your own journey also.

1. Mindset: “Not knowing is more intimate”

Since I’d done something reasonably successful, it was easy for me to get trapped in the “now I know!” mind. But as Hiten kindly pointed out to me, it is exactly what’s holding me back from going back out into the world and producing another success or doing something fulfilling and long-lasting.

There is a funny paradox about life, success, and business I’ve learned before but keep forgetting: The less you claim to know, the higher your chances of becoming successful. Developing this mindset can be challenging, and I’ve learned more about this from my time living in a Buddhist monastery, than all my time in Silicon Valley and building startups combined.

I find this mindset hard to fake, liberating to embody, and intensely scary to trust into. To “not know” means to become insanely curious about the world and the people in it. What do people really need? What is actually hard and challenging in life? What parts do I and others wish were more easeful and enjoyable? It requires me to sit with the discomfort of unanswered questions and stay there.

We’re looking for the kind of wide-eyed curiosity of a child that’s just found a funny-looking rock at the beach, which he or she is turning over, again and again, exploring its textures and shape. And at no point, the child assumes it “knows” the rock they are holding, yet continually giving it their full attention for ongoing exploration.

If you have developed and mastered this mindset, the world is yours. Easier said than done of course! There are tried and tested ways to develop this kind of mindset. Some of my personal favorites:

• Coaching
• Imagery work
• Meditation
• Therapy
• Sauna
• Journaling
• Long, boring walks in nature or through the city
• Spending time with kids as they play

Have your pick and explore which ones work for you. Luckily or frustratingly, there’s never an end or a finish to this process. I can always discover more about the world around me, and become more intimate with it as we cultivate our “not knowing” mind.

I found that this ongoing practice of warm-hearted curiosity will be supportive not just for building a business, but for life, and all its relationships in general.

2. Essence of service: Defining your basic question about the world

Equipped with wide-eyed curiosity for the world, we can now choose which particular question or challenge we’d like to give our attention to. This is again like the toddler at the beach picking up a rock – he/she needs to pick up A rock, it can’t look at all of them at the same time.

The question becomes – which rock calls to you to explore? It is usually intertwined with your personal history, preference, set of challenges, and learnings throughout life. In my case, the basic question about the world that I’m exploring with Here for example is:

• “What creates connection and belonging online?”

A random selection of basic hypotheses clients have discovered for themselves that I remember from working with them over the years are:

• “What makes for a fun, productive, and powerful meeting?”
• “What is a breakfast that is healthy, filling, tasty and good for the planet?”
• “What is powerful mentorship?”
• “What creates a sincere and successful entrepreneur?”
• “How can we live in more harmony with the planet?”

The fun part is that you can keep evolving and re-stating your basic question about the world as your product or service and you as a person evolves.

The second good news is that you’re not required to answer that question. Your only task is to keep asking it, to yourself, to your team, to your customers. You live into the question without ever needing to find an answer for it. Fun!

3. Focus: Who exactly are you going to serve?

Now that we have a curious mindset and selected a nicely shaped rock that’s called to us, I relearned to ask: Who exactly are you going to serve? There is a big challenge and mistake that I thought I’d outgrown, but evidently, looking at my thoughts and actions of the last few months, I haven’t! It’s to want to serve EVERYONE. “Well, my product is so good, EVERYONE will need it!” my mind would proudly tout.

It’s well-intentioned, and yet also the death of every attempt to bring goodness and service to the world. The old adage is true when we try to serve everyone we serve no one.

Luckily, there is a simple answer to this question of “Who should we serve?” and it’s: People like us. This is the single-best route for a sustainable and enjoyable journey that I know. In the therapy and coaching world, for example, I often hear stories of how clients ALWAYS bring topics that are so close to home for the coach, therapist, or practitioner. That is of course by design, we want to help people with challenges and questions that we ourselves have also explored, even though not necessarily answered.

I don’t mean this in an echo chamber “people that think and talk like us” kind of way, but more in the sense of serving people that feel similar itches and challenges to us in their lives.

There is a big caveat to this. Generally, people, if unsuccessful in choosing their focus well, land in one of two camps:

• The savior camp: The savior notices a problem that lots of other people have and attempts to solve it. He or she might even solve it well! Only problem: after a few years, as the business is potentially booming, there is a strange disconnection that emerges between the entrepreneur, its customers, and the business. The challenge that the business is now solving reasonably well, has nothing to do, in any shape or form, with the personal challenges that the savior has. This is trouble! It will eventually lead to burnout, depression, or if it’s recognized, to a pivot where the savior is able to readjust the business to solve a problem that is actually personally meaningful to him or her.
• The self-centered camp: The egoic person notices a problem that he or she has and that ONLY he or she has. They spend no time whatsoever exploring the world around them and asking whether others also have this problem in this particular shape or form. This is trouble! Most of these business attempts don’t become successful. And if they do, the customer rarely feels fully heard or understood, because the problem isn’t solved for them, but for the original, egoic person.

Ideally, you want to take ingredients from both the savior and the ego camp and combine them, and to generally hold the whole mix with a spring in your step and elasticity so that it doesn’t become static. This needs to be liquid and fluid so it can move around to the left and the right when it needs to expand. It probably needs to be regularly re-evaluated and recalibrate.

The middle ground looks like this to me: You’re solving for a problem that you yourself have or have experienced pain around, but you’re leaving enough room for interpretation that other people’s experiences can resonate and relate without needing to EXACTLY overlap with yours.

A client I coached went from solving for all people that like to eat food to people that earn above a certain amount of money AND tend to shop at a particular set of stores to narrow it down, plus a few other parameters. The language immediately changed.

At Here, the community platform I’m building I was excited to build for ALL communities out there at first. But then, narrowing it down to say that Here is built for communities focusing on Coaching, Yoga, Meditation, Therapy, Journaling and other mindful peer-led or facilitator-led groups has been a big relief!

4. Process: How to learn from and reach out to your ideal customer

Now we’re going into the nitty-gritty a bit more. After rediscovering the importance of a powerful, open-minded mindset,  we paired it with a distinct wish for serving the world. And then focused that view on a set of people that are like us, not too much, not too little. Now let’s get to work!

And that means one thing first and foremost: Talking to people. Ideally to the people that are in the group you identified in step 3 above.

Before you talk to them, my friend Hiten has often reminded me to begin with writing down 3-5 hypotheses. These hypotheses you carry in your back pocket. But you don’t ask them directly.

The hypothesis format follows “If…, then.., because…”, to pull some examples:

• If someone uses your product/service, then they have 4 extra hours a week to spend with their family, because they can do their accounting in half the usual time
• If someone uses your product/service, then their level of anxiety will decrease by a mark of 1-2 points out of 10, because their ruminating thoughts have been brought to paper
• If someone uses your product/service, then they will grow their business by 30-50%, because they can find contacts that matter to them faster.

In general, phrase hypotheses in a way that you can have a yes/no answer at the end.

The book that helped me the most to learn the right interviewing format and process is called “Lean Customer Development”, by Cindy Alvarez. She suggests taking notes as you’re into the interview around the following 4 points:

• Something that validates your hypotheses
• Something that invalidates your hypotheses
• Thoughts/sentences that take you by surprise
• Thoughts/sentences full of emotion

Cindy also devised an interview script for how to talk to customers and I’ve modified it a bit below. In general, questions are guideposts, you can tweak them and change them in the way that you feel that they will land the best with the customer. Good questions are those where there is no right/wrong answer. The best answers are those where the customer talks about past actions, not thoughts or ideas.

Example of a customer response to your question “How does mentorship fit into your life?”:

• Helpful answer: “Last week I had 2 calls with mentors of mine for 1 hour”
• Not so helpful answer: “I love getting mentored and offering mentorship to others!”

The reason the second one is much less helpful is that it is much less of a distinct predictor of future behavior, which is what we’re after.

The Interview Script

Questions to ask (you’ll see they evolve very little around the product and mainly around the problem):

Give me a bit of context about yourself – if you’re building a business product, you can ask “What is your name and role at your company? How do you fit into your company’s department structure? Overall in the company?

Tell me about how you run/do  ___X___ today…. (X is your general, broad area of focus, i.g.: “eat breakfast”, “have mentorship calls”, “run meetings”, etc.)

What [tools/products/apps/tricks] do you use to help you get ____X___ done?

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.

Last time you did ____X____, what were you doing right before you got started? Once you finished, what did you do afterward?

Is there anything else about _________ that I should have asked?

(Dig deeper into their typical day on anything that sounds painful or expensive. (You can add some hyperbole here to get them to rant a bit by saying things like “that sounds inefficient…” or “that sounds expensive…”))

To summarize again, the most important part is the mindset. Enter these meetings with the sole wish to understand the customer as a human and then their problems better. Tune into their feelings, wishes, grievances. Together with their input and your own creativity and inventiveness you can build the most powerful and useful product.

Last words

In relearning these lessons over the last few months, I used the points in this article not as a concrete map, but more as a compass. At the end of the day, building a business, whether you’ve experienced it before or not, is messy. You may encounter and explore the 4 points I focused on here in random, messy order, go back to one, iterate on another, and so forth. At the end of the day, trust your intuition and your groundedness in the feet and the belly.

I hope some of this has been helpful for you too as I’m distilling my own process in the middle of this new adventure. Let me know if I can help with anything.