Entrepreneurship, the Second Time Around

A note to my future self as a founder.

Image edited from Juan Pablo Bravo.

I have started a company. I have also shut down a company. No, I didn’t conjure up a post-mortem post claiming to be happy about closing. It was hard. But I did write some notes to myself at the end of it all on mistakes that I should not make again, the motivations I need to remind myself in the thick of it, and the goals I should set with my next company. That was about two years ago now. As I move onto my next venture, I was looking back at these notes, and I decided to share the ones I’m finding most helpful now. Enjoy!

Don’t let your emotions deviate too far from the middle.

I keep thinking about a quote a friend at a hedge fund told me: “It’s never as good as it seems or as bad as it seems.” The movement of markets and a founder’s emotions are not dissimilar. You’ll get pegged by a copious amount of inputs, things that you can constantly react wholeheartedly to : a potential partnership, a dissatisfied employee itching to leave, friends telling you it’s not going to work, etc. And if you let each of these happenings swing your emotions, you’ll get tired and demotivated quickly. Stay your course. No isolated occurrence will make or break your company.

Look ahead, not left and right.

Any good market will have competitors or incumbent players, often both. But it’s up to you to build your vision of the world. If you look around too often, you’re going to end up like the rest of them — undifferentiated.

Hire slowly; fire fast.

It’s the least intuitive thing ever, I know. It’s so easy to get excited about prospective employees, and since you’re always pitching, you may find yourself selling the candidate on the role before knowing it’s the right person. Slow down. Make sure this person is who you need to hire right now and that the rest of your team likes them. Layoffs are the worst.

On the converse, fire fast.. Don’t worry — it’s pretty much impossible to do it prematurely; it’s already so difficult to even get to the stage of thinking of firing someone. However, you often feel for them. You think about the ones that depend on them outside of work and hey, they may even be a good person outside of work, too. But for the company’s sake and for their sake, let them go quickly. Toxic employees are dangerous and contagious. The longer you let them fester at your company, the worse other employees feel as well. They probably aren’t performing at their best because it’s not the right role or company for them, and that the faster they can get to that role, the better. Or at least that’s what I tell myself to go to sleep at night…

Listen to your body.

You’re CEO now; there’s no need to force yourself to work 15 hours a day if it’s not productive. Work hard, but if you’re hitting a wall, it’s up to you to take a break. Ask yourself this: are you here for a quick 1–2 year flip or do you want to build a multi-generational company? If the latter, you’re going to need to not burn out in 2 years. These things called startups take time.

Outlast everyone else.

Startups are supposed to move fast, right? Well, they do, but only relative to larger enterprises. Patience. Sales take time — don’t force your clients into premature answers. Product takes time — don’t make every feature decision on the fly. Building formidable teams takes time — people will come and go in between.

My theory: the true winners in any space are the ones who outlast everyone else. By staying alive longer, they get over the humps that deter everyone else from accomplishing the mission. They develop deeper insights and have better knowledge of the field just by staying conscious of the problem space longer. Don’t give up.

Your job is to be a constant.

Your job as the CEO is to be the rock for your team. You need to be even-keeled even when the environment around you is mayhem. Your employees need to believe that the team can be able to get out of the ruts that occur; they will look to you for a sign of that direction. Remember, no one event or person should be able to make or break your company; act accordingly, and don’t let a single occurrence bum you out. Verbal or nonverbal, news spreads quickly in small companies. Be aware of every move you make. Everything will be okay, also.


8+ hours a day cures many problems. Trust me. If you can’t change your sleep schedule, how can you change anything?

At first, your business is just a narrative.

Let’s be honest, you don’t have much else — maybe a couple customers/users, maybe a 45% functioning product, etc. The first users are there because: 1. They believe in the mission of what you’re building and 2. They believe in you and your story. Share why you’re doing this more often; share what motivates you. Share the vision you see for the work you’re doing and why it matters. That’s really where it starts.

You’re not drafting. You’re at the front of the pack.

Okay, this is probably a bad metaphor, but bear with me. In cycling, bikers can save up to 40% of their energy by “drafting” off the leader. It would be cool if you could do this in startups, but nah, you’re at the front. There’s also no one else in the race. So you have to take on the burden of setting the pace — how you hire, the way you approach the market, etc.

You make the final calls at the end of the day, and there’s nothing to compare your decisions against. They just are. But that mental energy of having the weight of your future and the futures of the people around you is heavy; just know that you can set the pace because you and your team are in the race on your own.

Stealth mode is bullshit.

Almost all the companies I’ve seen in “stealth mode” have nothing worth hiding. It’s often a front for a lack of product vision or a fear of failing. The best ideas are socialized; they build upon the ideas of others. Only when you share your idea with others will you be able to learn how to fine tune it and make it better. Otherwise, it’s a pipe dream. Also, it’s incredibly arrogant to believe that you are a lone genius.

*The only slight caveat I’ve seen with “stealth” is when a team raises immense sums of money and doesn’t want to draw attention to their product by direct competitors/giants.

Get a therapist or executive coach.

The biggest reason you may lose is not the market or the lack of funds but rather, it’s you. It’s the existential dread and the loneliness. It’s the lack of motivation and the fear of losing. It’s the mismanagement of one’s mental health. Such a thing can shift your previous optimism of the product and how you treat others. It affects everything from how you think about your product’s features to how you walk into the room in sales meetings. Find someone who can help you think through your personal issues inside and outside of the business because they flow right into your every day work. It’s all connected.

Make decisions from conviction, not fear.

Decisions are super easy to make in reaction to events that come at you: an angry employee, a funding round that has fallen through, etc. Take a step back and think about your next move. Is it in reaction to what just happened (fear) or would you have made this decision independent of your immediate surroundings (conviction)?

It’s lonely at the top.

Well, let’s assume the “top” is ultra relative because you have nothing yet, and there’s much to be built. But I mean “top” in the sense that you are a founder and a final decision maker. Some things you can’t tell your employees or investors. Some things your friends and family won’t understand. Some problems may be directly between you and your co-founder. At some point, there are issues that you have to work through that are in the center of this hellish Venn Diagram. And believe me, that’s when you feel the loneliest — who do you go to?

For me, I found a few trusted founders of other startups in different spaces. Often, they knew exactly what I was going through and other times, they knew how to comfort me because they had been through something similar. They had no stake in my life or business, but that’s what was great. They didn’t have an incentive to lead me the wrong way but rather were just paying it forward to another founder.

Don’t beat yourself up over unproductive time.

Self-loathing doesn’t solve anything. We have good days, and we have bad days. Some days, you just need a moment to breathe and to reset whatever crazy cuckoo clock you have going on in there.

Your customers are in on a secret.

You need to make your customers feel like by using your product, they are living in a future — a future in which they are ahead of their competitors because they know something that their peers don’t.

Trust the process.

We live in an age in which experimentation is king, and all decisions need to be informed by data. It’s great, but if you run your entire company as an experiment, you’ll never derive the momentum to come at the market with a contrarian or differentiated view. Early on, experiments fail. A lot. If you take it to heart every single time, it hardly ever works. Sometimes, you just need to have the conviction that an initiative is meant to exist and that it has to work. And then you have to trust that it will, even when early signs point the other way.

It sometimes astounds me that I would want to put myself through this again, especially after the first one having gone completely south.

It sort of goes back to my first point of it never being as good or as bad as it seems. I learned that the “bottom” of any startup life has a limit. You’re sad. You wallow for a bit. And then, there’s nothing left for you to do but to get back up. One day, you’ll want to do it again, except this time you will have even more support than the first time. The people who matter will rally behind you once again, stronger than before. Take it from someone who’s on Startup #2.

Thanks for reading! If any of these bits struck a chord with you, please press👏👏👏 (a few times) for me.

In case you want to keep reading other things I’ve written, here’s one on email intros: