A young girl with a lemonade stand
Image credit: Steven Depolo on Flickr

How to change an entrepreneur’s life

You have far more power than you realise

Kaila Colbin
5 min readFeb 21, 2021


I started my first business when I was 6 years old. New York City, 1979: I’d take a pile of books from our house, lay them out on the sidewalk in front of our apartment building, and sell them for whatever I could get.

It was an unbeatable business model for two reasons. One, people find little entrepreneurial kids so cute that they are willing to be absolutely fleeced by them. Two, my cost of goods was zero: I basically stole product from my mom, who let me get away with it [see reason #1].

I became a partner in a business in Miami when I was 23, distributing large-format digital printing supplies to Argentina. “Large-format digital printing supplies” = all the raw materials that go into making giant billboards, or bus graphics, or window signage: giant rolls of paper or adhesive vinyl, giant jugs of toner, etc.

I say “I became a partner in the business” rather than “I started the business” because it would be overly generous to ascribe any level of intentionality, sophistication or skill to what I was doing. I met this older Argentine dude who said I should work for him and he’d give me 20% of the company so I could be an “executive” and a “business owner,” which sounded just fine to me. I thought he had all the answers and I was happy to follow him.

He had a printing company in Buenos Aires that was effectively my only customer. Instead of a glamorous “executive business owner,” I was essentially a glorified purchasing agent, buying, consolidating, and on-shipping the inputs to his South American business. When the printing company went under, so did I.

I became a partner in another company right away, following another man who had answers. We wrote books and produced videos and created a traveling stage show to teach kids and parents how to use computers and the internet.

We were reasonably good at what we did but not good enough. Over time, for all sorts of tiresome reasons, my relationship with my business partner deteriorated. We called it quits right around 9/11.

I was exhausted and broke and moved to Colorado where my sister took me in and fed me. I got a job with a paycheck and hung out for a few years until I met a Kiwi guy and decided to move to Aotearoa New Zealand with him.

Around a year into my new life, I went along to a businesswoman’s networking lunch thing. There were maybe 20 of us sitting in a U formation and the speaker, Melissa Clark-Reynolds, had us introduce ourselves. When it got to me, I said, “My name is Kaila Colbin. I started two companies and they both failed.”

Without a moment’s hesitation, Melissa replied, “You need to start another company. Immediately. Before you forget all the lessons you learned from those first two.”

I was shocked. How was it possible for someone to believe in me, be kind to me, encourage me? How was it possible for someone to extend grace to me? Maybe she hadn’t understood the “failing” bit? But no, she was serious. We became friends. I became a founder shareholder in one of her ventures. We had our ups and downs. But I never forgot that moment:

“You need to start another company. Immediately.”

This week, my friend Jake Millar is being raked over the coals because a company he started, Unfiltered, did not achieve the lofty heights he envisioned for it. He sold it, possibly at fire-sale levels. A couple media outlets have reported that some of his shareholders aren’t happy.

I don’t know all the details, but I recognise the glee with which people are piling on. They’re mocking the hype and suggesting all entrepreneurs are con artists. These people definitely would have known right from the beginning that the business wasn’t going to work. To them, it was all completely obvious and everyone should have known how it would end.

Nelson from The Simpsons pointing and laughing

But building a company is hard. Any investment can go sideways. Even huge businesses fail with startling regularity, and startups face a dramatically greater level of uncertainty. It is always a gamble — always.

If having a company go bad is grounds for damnation then no one should start a company, ever.

Having a company go bad is simultaneously one of the cruelest of punishments and one of the most powerful of teachers. Every single mistake is seared into your neural pathways forever. You forget the things you learn in business school, but you never forget the lessons you learn when it’s your own ship that’s sinking.

And while I am not naive to the fact that con artist entrepreneurs exist (yes, Fyre Festival, yes, Theranos), I do not in any way believe Jake is one.

I met Jake when he was 18, shortly after he started his first company, Oompher. I was impressed with him then—I couldn’t believe someone so young could have his level of maturity—and I haven’t seen anything to diminish my respect for him.

Yes, he maintains a flashy public image: fancy clothes, fancy cars, fancy parties. He is also kind, serious, hard-working, generous. He follows through. He is attentive to details.

It’s a mistake for us to tear him down because things haven’t gone the way he hoped. If he did something illegal, sure. If he behaved unethically, sure. If he robbed or stole or cheated or kicked puppies… yep, all of it.

But he did not. He had a dream, and—this time around—was unable to make that dream come true.

When a company fails, having someone extend you grace may be the difference between whether you fail with it or whether you live to try again.

Melissa extended me grace, and it changed my life.

You have the power to extend that same grace to others.

Will you?



Kaila Colbin

Founder/CEO Boma. Dual citizen USA/NZ. Certified Dare to Lead™ Facilitator. Just wants the world to be a better place.