5 favorite Bootstrapped Giants posts of the year

Hi, Andrew here today. I’m stepping in for Jesse, who’s with his family this week.

I want to highlight five posts he wrote in 2026 that had the most significant influence on me as a founder and leader — and that I believe will have an equally powerful impact on you.

I partnered with Jesse because I wanted his approach to business to rub off on me. And it did.

But I’ve found that the biggest lessons, the ones that sink in most, come from issues of this newsletter, where he has space to go deep on a topic, and I have time to really think through it.

These are the ones that sank in the most.

A founder once asked Jesse, “When do you stop reaching out to a prospect?” Jesse turned on Zoom’s screenshare, opened Superhuman, and showed him multiple emails that he sent to a prospect.

They were short, funny, and pleasant.

The founder got the point. So did I. Don’t stop when you’re being ignored or they’re reluctant. But don’t be a pushy salesperson either. Be pleasantly persistent.

As I book interviewees for our new podcast, I’m constantly thinking about that approach.

Most people don’t respond, or say “maybe another time.” Instead of being hurt, I continue to send them fun notes.

This post has a detailed breakdown of the approach, along with a story of how it landed a client.

Read it here.

Scroll down to the section headed “A Solid Founding Team.” That’s the gold for me.

As a life-long founder, I sensed that I was taking on too much, but I never understood how to think about what I should do and who I should partner with.

Then I read that post’s description of the 3-person founding team:

• Sales/marketing “GTM” person

• Product/tech/delivery person

• Ops/admin/finance person

I always take on at least 2, if not 3, of those roles.

In the early days of Bootstrapped Giants, I did all 3 — and I refused to hire the operations person until the Gateway X team helped me see that I suck at organization and I hate doing it.

We hired Lauren Katz as our Chief of Staff, and now I get to spend more time on what I’m great at.

Read it here.

Things haven’t worked out at Bootstrapped Giants the way I expected.

In 2026, we’ll split it into two companies/projects: One that focuses on Jesse’s leadership writing (what people love about this newsletter) and another that will help grow AI companies (what you’ve seen in my new podcast).

I’ve been gung-ho about moving forward, never allowing myself to feel bad about what didn’t work out.

But the sadness and disappointment are there. In the back of my mind. So is a sense of guilt for not being able to do what I set out to do.

I kept it all in the back of my mind.

Until I read that post.

There’s a section of that post where Jesse lays out what did and didn’t work out for him with Gateway X.

Then he says, he wants to “FEEL the sadness” of what didn’t go as he wanted. “Why?…by feeling it, I clear the blockage.”

I’ve been letting myself feel the sadness too.

Read it here.

This is the one readers loved the most last year.

It’s about spirituality.

I’ve always resisted spirituality in business. But the approach in that post isn’t woo-woo.

It’s practical. For me, it’s about finding the place where I’m open, curious, creative, and filled with love. And when I’m there, work is better — and I’m happier.

Read it here.

The weird thing about entrepreneurship — at least as I’ve done it over the years — is that you have to believe you’re right when others say you’re wrong.

When I graduated from school, I started an email newsletter company, when everyone said newsletters can’t be profitable. I held firm. I was eventually proven right.

That stubbornness also kept me from hearing harsh feedback about myself. And kept me from being a better leader.

In that post, Jesse laid out a framework that helped him be open up to his teams’ feedback, and made him a better leader.

My favorite line: “Everything has truth in it, so instead of asking IS it true or not, to learn/grow, always ask yourself: ‘How is what they’re saying true?’” -Dave Kashen.

Read it here.

~andrew