Recently, I decided to step down from a company I co-founded.

Looking back, I’m super proud of what we achieved in such a short amount of time. It was an incredibly fulfilling experience that confirmed I want to take another swing at it soon.

Here are my reflections on what I learned from the experience.

Any baggage you have intensifies at a startup

Startups are all-consuming. 12 hour days, 5-7 days a week. One thing that kept creeping up was that any weakness or insecurity I subconsciously suppressed over the years were forced out in the open. Over time, the business and team started feeling it too.

• Do you avoid confrontation? Get ready to face it every day through sales calls, team dynamics, and sometimes difficult customers.
• Are you a people pleaser? The more agreeable you are, the more you waste precious time and energy depleting your startup's chances for survival. Worst case: you'll grow resentful and tired.
• Do you have a hard time asking for help? Things won't get done faster if you don't ask! Don't be the bottleneck.

Are you self aware enough to acknowledge them at all? I was (am?) all of these.

In the very early days, you and the company are basically the same. Your insecurities will bleed into the company’s every day. Getting a therapist really helped me identify these tendencies and keep me accountable.

Learning to trust your gut

Coming from engineering backgrounds, we defaulted to analyzing every decision to death.

Big companies train you to think this way - run A/B tests, track KPIs, analyze cohorts. At a startup, this can be a trap. Thankfully I quickly realized this was the worst way to do things. You can’t make 100s of decisions every day this way.

Over time, something interesting happened. I started listening to my gut. The more confident I got, the more a decision “felt” right. Should we invest in [expensive thing] now or later? Should we partner with this investor or not? Whenever I walked out of a situation, I paused and listened to how I felt.

In retrospect, most, if not all of those “vibes” based decisions turned out to be the right move for the company.

I wish more startups talked about this. “Do what feels right” seems weird to say, but in practice, that’s how it is (assuming you’ve done your homework of talking to customers and building some expertise in your area)!

Looking back, we were essentially afraid of making mistakes and thought everything needed a “right” answer. But that’s the thing - there’s no way to know until later. Instead, the best you can do is gather enough information and commit to a decision. You can always change and adapt later!

I found a conversation with Patrick Collison where he discusses exactly this:

• “…there are many decisions where you cannot possibly make an informed decision based on complete information”
• “make decisions quicker, and then course-correct when required”

Confidence

Confidence might be the most underrated founder skill. Not because no one talks about it, but because it’s the invisible force behind everything - defending your idea from haters, pitching prospects who scrutinize you, painting a bold vision that may or may not be right.

In one of our first ever sales calls, one prospect was particularly offended about our pitch: “I can build this in ChatGPT over a weekend. Why would I pay for this?”. I wanted to disappear. I stuttered a response, trying to defend myself.

It was a slap in the face, but it was a good reminder to do better. I believed in our idea and what we had built, but didn’t have the know-how to communicate that clearly yet.

Over the next few months, I put my reps in. I talked to more customers. Pitched at conferences. Noticed patterns in customer pain points. Every hit of validation gradually boosted my confidence that we were on to something.

At the same time, I worked on my delivery and presence. I tricked myself into speaking with authority, apologized less, and shared my opinions over things I cared about. Slowly but surely, the message started resonating. Conversations flowed more easily.

This newfound confidence was crucial for business. Looking back, I can pinpoint exact moments where it directly helped us close more deals.

As a software vendor, data security is a common concern in sales. We’d pour in hours of work, get near the finish line, only to be blocked by IT for security reasons. We said all the right words too: security certifications, encryption in transit and at rest, zero AI data retention, etc. But still, they weren’t comfortable with our security. Why?

After some coaching and practice, we tried again. Finally, we started closing deals. Breezing through security reviews. What changed?

Confidence! We walked into those meetings differently. Instead of listing qualifications, we opened strong: “We work with companies like yours all the time. Here’s a handbook we prepared that lists everything you’re probably wondering”. People felt a difference in the way we moved, and decided to trust us for it.

Practicing Confidence

Some things that helped me practice confidence:

• Put in the reps (nothing beats good old fashioned hard work)
• Show up prepared (anticipate their objections; answer their questions before they have a chance to ask them)
• Be more opinionated (you care about certain things deeply - share them!)

Other things I learned

• Everything is figureoutable™. Confidently believing that you can and will figure it out is a superpower. That’s the one constant as a business owner; you’ll have to do things you’ve never done before over and over.

  Before this, I had never:

  • Written a business contract or sales deck
  • Negotiated price and terms with vendors
  • Gotten security certifications (SOC2)

  But your attitude here is crucial. One thing that’s helped me here is to say out loud, “I’m not sure, but I’ll figure it out”. Eventually, it becomes a flywheel: the more positive reinforcement you get from overcoming one hurdle, the more confident and prepared you are for the next.

  The most impressive teams I’ve seen in my career had this attitude about their work.

• Not everything you do needs to feel productive. It’s easy to guilt yourself into doing something “productive” ALL the time like replying to emails at midnight or listening to business podcasts in every commute.

  Instead, I feel my best when I give my thoughts room to breathe - whether it’s through long, wandering walks, letting an idea sit for a few days, or doing something creative. Not only did this lead to more “what if we just…” moments that led to some key decisions, but it also made things fun again.

Closing thoughts

One truth I’ve internalized through this experience was how much being a founder has to do with managing your psychology.

Going in, I thought the hardest part would be solving business problems or engineering a complex system. But the real hard part is managing your attitude and headspace as you struggle in ways you haven’t before.

Reflecting on my experience, I’m so glad I decided to make the jump, even if I didn’t end up staying at the first company I started. It’s hard to imagine going to a full time job after the freedom I felt in having full control over my every day.

I learned a lot more about myself than I expected from this experience, and I’m excited to tackle the next company with even more confidence.