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Bootstrapped Giants

Painful news about one of my companies

Published about 1 month ago • 5 min read

In the last few weeks, we made the tough decision to pivot Unbloat, our e-commerce brand, from a growth focus to “profit max.”

That has meant parting ways with all our agency partners, pulling most of the team off (luckily we placed them with other GX companies), and most brutally: looking back at the last two years and realizing we were wrong.

Today’s email started as a card in Notion.

After I wrote the email, the card was assigned to my editor. When he finished, he assigned it to my designer. When she finished, it was assigned to our COO who likes to review it. Etc.

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We didn’t have the success we wanted.

In time, I’ll go much deeper into what happened, what we learned, how we approached this decision, and where it all ends up. I’m writing to you before I’ve had time to process it fully.

But, as I’ve been reminded in the last few weeks… entrepreneurship is hard. And you will never be a success without lots of failures (trite, I know, but true).

A few weeks ago, when I asked this newsletter’s readers what you wanted me to write about, “when to quit,” was a repeated request.

It’s a question I’ve always struggled with…and continue to wrestle with. Quitting could mean stopping. Pivoting. Letting someone go. Or something else.

It’s making a major change in whatever direction you’re going.

It’s emotional, scary, and ALWAYS unclear. And by design, we entrepreneurs are THE WORST at it. Our whole identity is tied to making the impossible, possible. Defying the odds. Etc.

So, Jesse. How do you decide when to quit?

I DO NOT have a killer framework. But here are a few things I’ve done that work. (Hit reply and tell me your approach!)

This has been my most successful approach. Something Ric Elias also does.

It’s sort of obvious, but I’ll explain: pick a certain amount of time, a very clear metric, and where you hope to be.

For Unbloat, it was trailing 30D ROAS of >1.4. And we gave ourselves 6 months, back in December.

Then you commit that, no matter what, you’ll make a big change if you don’t accomplish it. Be sure to match the time to the metric.

E.g., if you are trying to double something in 2 weeks, you’re setting yourself up to fail. You need enough time to reasonably believe you’ve given the goal all you have.

And when you pursue that goal, be sure to give it all you have. Leave it all on the field!!

Once the time (or cash burn) has been hit, be decisive.

Here’s why this works: entrepreneurs are endlessly optimistic and determined. We could chase anything forever.

We constantly feel we need “just one more shot,” one more customer, an employee change, a different marketing channel, etc.

Timeboxing/Moneyboxing works because it forces you to avoid your rose-colored glasses. At some point, WHY things went wrong no longer matters.

Pursuing “one more shot” is throwing good time after bad. Is it the customer? The product? The person? Who cares? It’s not working. Make lots of changes. Or quit and do something else.

Time is your most scarce resource.

This is a military analogy that my coach taught me. It describes either moving forward or retreating and reevaluating.

Here’s how I use it. Often, after a year of grinding at something, you know it 100x better than you did prior.

But humans are inert creatures. We get used to our day-to-day. We stop asking big questions. Even slowly failing can be comfy.

So I stop. Get offsite. Take a step back and ask: given what I know now, even if this thing gets to its 10/10 ideal state… DO I ACTUALLY WANT THAT??

I did this with Kahani, the e-commerce platform I launched. Once I understood the grind of SaaS ecomm, and what it would take to succeed, I projected myself 2 years into the future.

Then I asked myself, “EVEN IF everything works out, do I want that vision?”

Turns out, I did NOT want that. I wanted to build Gateway X. Not a SaaS ecomm biz.

Clarity ensued. I shuttered Kahani and I’m thrilled to work on Gateway X.

It’s easy to lie to yourself on this one. So be sure to have people you trust keep you honest.

I have a good friend who sold his company. He hates the new owners. They stupidly treat him like a cog in a machine.

But, they put him in golden handcuffs. He has a guaranteed big bonus after 2 years of staying at the company. And he’s miserable. He feels stuck. Hates it. But a big payoff is right there.

We started talking. I asked, “If you left tomorrow, what would you do?”

He looked surprised. It was clear he had never seriously thought about that question. We workshopped what the alternative could look like. Explored a new idea he’s been kicking around. Thought about health.

All of a sudden, the current path didn’t seem so ideal. And the alternative felt less scary.

You can do this at any level of an organization. For an individual, consider time spent on another project. Or an alternative marketing channel. Or an entirely different business.

What’s a viable alternative? Paint the picture and watch yourself shift/quit to success.

There you have it. 3 mental models that can be used together to help you decide when to quit/pivot.

Talk to people you know and trust.
Sometimes it’s really hard to see it when you’re in it. Your spouse. A best friend. Other mentors. It can seem so obvious to others and not to you. With Kahani, my Ampush cofounder unstuck me. He called me out.
Let go of your stories about failure and being a “quitter.”
This kills more startups than anything else. The founder “goes big or goes home.” So rather than making important changes, they sink with the ship and end up in a job they hate.
Remove yourself.
A simple mental model, but consider if someone in a similar situation asked you for advice. What would you tell that person to do?
Notice your emotions.
We founders (especially men) love to pretend we’re objective. Bullshit! We are emotional and low EQ (at least I was). This is dangerous and leads to bad decisions.

2 related thoughts:

Another framework: 3 strikes.
Most things I’ve tried never work the first time. But if I give something 3 big swings and it still doesn’t work, it will almost never work. So 3 strikes means it’s time to quit.
A corollary to the above.
When something is working, I’ve NEVER asked “Is this working?” You know why? I’m too busy trying to fulfill demand. That’s been the case for GrowthAssistant and Aux Insights, two of my most successful companies.
I never had that experience at Unbloat or Kahani, the ones that didn’t work.

But you never really know

Despite all the frameworks and mental models I shared here, it’s important to say that you never really know if it’s the right decision.

But once you decide, you have to move forward and not second guess yourself. You can’t look at someone else who’s successful, compare yourself to them, and beat yourself up. That’s the path to unhappiness.

This decision is the toughest I’ve had to work through recently. What are you going through?

-jesse

Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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