person surfing

I’m (still) not crushing it

A decade ago, I wrote a blog post about how I was not crushing it with my startup LaunchBit.

In that post, I added this graph:

It looked good — up and to the right (though no labeled axes publicly disclosed). But, on a day-to-day basis, the graph looked like this and more importantly, *felt* like this:

Doing a startup is HARD, because it’s hard to see the long-term ups of where you’ve come from and how much you’ve accomplished. And it’s easy to see all the troughs you have to stomach today.

The headfake about my current company Hustle Fund is that even though we are a VC fund, we share many more similarities to our startups than we share with other VCs. This may sound counterintuitive, but we have revenue (with ups and downs of it – just like our startups) and lots of people (30+) who count on a paycheck. Managing money and lots of people is what makes companies hard!

I write this post, because I know that a lot of startups are struggling right now. Capital is tight. It’s hard to make money. It’s hard to console your team who may be worried about the market. I know – I get it.

An example of one trough that I’m going through right now is that I recently learned that I will have to personally chip in a lot of cash — more than I made last year — to cover a company tax situation. I know that so many startups often have founders contribute to their respective businesses to make ends meet. We all face the same issues. This won’t be easy for me. But we’ll figure it out.

In fact, the past couple of weeks or so have been the toughest point for me in our journey — even tougher than those first few months when my business partner Eric and I couldn’t raise that much money for our Fund 1. In many ways, it’s much harder to go through troughs when you’re a bigger company than when you’re two people working in a garage. (Ok, Eric still works in his garage).

A decade ago, I felt every trough so deeply. I was stressed. But there are a few things I’ve changed over time.


A few months ago, I spoke with one of our founders whose company is thriving. But, she saw her business go to zero during the pandemic and recounted how one day during the pandemic, it was just so stressful, she cried her eyes out in her empty office. I asked her, “What made you decide to continue your company and how did you ever pull through?” She told me that she realized that just being able to sit on the floor and cry about her startup was a privilege and that she wanted to continue.

That conversation summarizes how I think about my own startup problems now. It’s a privilege to be able to do this work day in and day out. No one is making me do a startup. It is a gift to be able to work with the amazing Hustle Fund team to get through problems – I am so so grateful.

So even though there are a tons of ups and downs in doing a startup, there’s no way I would give this up to do something else.

My health / habits

I’ve talked a bit on Twitter about how I’ve changed some of my habits which has made it immensely easier to handle stress.

Some key changes that come to mind include:

  • No phone before bed. I keep my phone in the kitchen
  • Use phone meetings to walk / jog to get exercise – there’s often no other time
  • Reduce meetings with voice messages via
  • Sleep early and wake up early to get a better handle on the day

These changes alone have helped me get a better grapple of not only my time but also my stress.

I also think being a second time founder helps. You know what issues can crop up and not much is surprising anymore.

But, The Ups and Downs are Always There

I think founders often think that if they can just get to the next milestone or the next round of funding, there’ll be more stability and fewer ups and downs. This couldn’t be further from the truth.

On some level, there’s more stability — there are more people to mitigate the chaos (assuming good processes in managing the team). But there’s also just more at stake and issues always arise, so the problems become bigger.

This is fundamentally what startups are all about. Constantly ploughing through and getting pummeled and rinsing and repeating. And this can be depressing for some founders. And, this is not for everyone — and that’s ok to move on.

But if you’re still excited to try to surf your startup wave, keep going! Everyone gets pummeled over and over again — you’re not alone — but just get back up on the board and continue. You’ll figure it out.

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One thought on “I’m (still) not crushing it”

  1. The world, and life, will always have ups and downs. It is a constant. The hope is that both the world and our personal lives don’t have challenges at the same time, but sometimes that happens, which is a good time to use the lessons we’ve learned from previous challenges, and then lean on those we know.

    And yeah, being an early stage startup today is a challenge. Sometimes an opportunity too, but that is usually only recognized in hindsight. Thinking what we are working on will be an opportunity certainly helps to keep my spirits up, but yep, these are challenging times.

    Let’s hope we learn good lessons from this time of “down” so that we’ll be better prepared for the next time.

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