Wait for “ready,” and it might never come
Three founders on the decision—and money—it took to take the leap.
My colleague Anita Little just published a piece on Shopify’s Newsroom about the gap between feeling ready to start a business and actually going for it. New Shopify x Harris Poll data from five markets found that an overwhelming 93% of aspiring founders in the U.S. say they feel at least somewhat ready, and more than half say they could start today*. They just haven’t yet. The tools and costs that used to hold people back have largely come down; what’s left is making the decision to actually start.
We wanted to hear more from entrepreneurs about navigating that process between I could start to I started. So we went back through the Shopify Masters archives and pulled excerpts from three founders who did just that. Below, in their own words, they explain how each of them decided to start, the real money it took to get off the ground, and what they’d tell you if you’re still waiting. —Leah Mennies
“When I say something out loud, I then must follow through.”
Nicola Hamilton, founder of Issues Magazine Shop, Toronto. Interview published September 2, 2025. Watch the full episode.
”I’m a magazine art director by background. I’ve helped make magazines in this city for a long time, and when I traveled I’d go out of my way to independent magazine shops and bring back ten pounds of them. My suitcase was always overweight. Nothing like that existed in Toronto, so opening Issues was kind of a selfish endeavor. It’s something I really wanted to exist, so I built the space of my dreams.
The day Issues became real was the day I sent an email with the subject line ‘I think I’m gonna open a magazine store?’ to Jeremy Leslie, who runs a shop called MagCulture in London. He was the blueprint, the kind of business I wanted to build. He was my first email. I sent it in April of 2021, I think, and that was the moment I was like, I have to do this now. I’m an Aries. When I say something out loud, I then must follow through. Whether or not it works, you wait and see, but I have to do it. Jeremy wrote back, ‘What are you doing on Tuesday?’ We got on a Zoom call and he shared as much as he could: numbers, distributors, the parts of the industry I didn’t know.
I know magazines, I know our product, but the business part I know less. I have no background in retail. [I remember] going to the bank and saying, ‘Hey, I want to open a print magazine store,’ they were like, um, no.
To get the loan, I went through Futurpreneur, an organization here in Canada for entrepreneurs under 40. You have to go through a business-plan-building process with a mentor, and that was hard. You’re constantly justifying numbers you’ve made up. A business plan is fully made up. You haven’t done it yet.
There’s nothing like us in Canada, so it’s hard to compare. You can look at London or Lisbon or New York, but those markets are different. You’re making your best guess. A friend who’d gone through the program before me ran a store in the same neighborhood, and I went crying to her one day. She told me she’d actually written two business plans at the same time. The one she knew she’d eventually get to, and the one she had to present to the bank. They just wanted to see a world in which selling magazines could sustain itself.
I got a $60,000 loan. $20,000 came from Futurpreneur and $40,000 from the BDC, the Business Development Bank. Then I invested about $60,000 of my own money. That’s the $120,000 we started with. It’s a five-year loan, but they give you the first year without payments, so you get time to get your feet under you before you start paying it back in year two.
The whole hypothesis was: there have to be more people like me out there who want this, who want to slow down a little. So far that’s been true. I did so much of this by accident, because I have no idea what I’m doing. There was no master plan. You can sit around and think about something forever, but if you just move into action and start doing stuff, it might not be right the first time, but you can fix it the next time.”
“I had an eviction notice on my apartment door.”
Olajuwon Ajanaku, co-founder of Eastside Golf, Detroit. Interview published June 18, 2024. Listen to the full episode.
”I’ve been playing golf since I was six years old. I was raised on the golf course in East Atlanta. I wanted to turn back pro at one point, and that was after I was in commercial finance for eight years. The whole thing was I couldn’t find any sponsors. So I created this logo. I was going to put it on my bag and put it on my polo and turn pro, and it was just going to be my logo.
I showed it to [my co-founder] Earl [A. Cooper] and he was like, you need to put that on a t-shirt. I ironed it on, went downtown in Detroit for a couple of hours, and I maybe got stopped like 120, 130 times. Who are you? What’s that logo? Where can I get it? Do you play golf? From there I was like, damn, I got something, but I still don’t know what it is.
I ended up creating t-shirts, socks, lapels, umbrellas, sweatshirts. The first 3,000 orders I shipped out of my apartment in Detroit. I started this brand because I was tired of being told no.
I’ll be a hundred percent honest, because we don’t usually talk about it much. Confidence for me to build this, it started out because I had no other choice. I had an eviction notice on my apartment door. I maxed out the credit cards, maxed out the 401(k), sold all my cryptocurrencies, and even borrowed the last $10,000 from a guy who sits on our board today. It was just a napkin signature, a handshake over the money. We paid him back a couple of years ago, about $25,000. I literally started the brand on LegalZoom. I didn’t have any other choice.
I was packing those first 3,000 orders myself. I’d fill up all the blue canisters at a USPS, and then all these packages have to go out tomorrow, so I’ve got to find the next post office. I’m traveling from Detroit two hours out, almost to Indiana, just trying to find somewhere to ship the packages. At the end of the day it takes belief, it takes grind, it takes grit. Sometimes there is no plan B. I hear it all the time, but I actually lived in it.”
“We bought our first logo on eBay for $50.”
Eli Khakshouri, founder, Retrospec, Los Angeles. Interview published February 6, 2023. Listen to the full episode.
”I was a student at USC in the urban planning school. Urban planning is a holistic study of what makes a city smart or sustainable, and a big part of that is transportation, walkability, and alternative ways of getting around. The more a city is built for cars, the less sustainable it is. Retrospec is very much an urban bike company. That’s the root of it. The problem we were trying to solve was helping people travel short and medium distances, with style, on something affordable that they’d love and be proud of.
I launched it in 2009, during a recession. I usually get the inverse of this question. People are usually like, why would you start a business when the economy was so bad? But what was really cool about starting at that time was that when we were looking for space, for vendors, for the relationships we needed to get off the ground, folks had time for us. Other companies were looking for opportunities to grow, to make up for lost business. That created an environment that was conducive to starting, to getting the attention of partners when you’re really small.
There was also the demand side. During 2008, 2009, 2010, there were stretches where oil got very expensive, and with paychecks and households constrained, people were looking for ways to save money. A bike is a one-time cost. So our offering was well timed for the downturn we were in.
I started this company with about $8,000 of my own money. I never raised outside capital or equity, and I still control the whole company. Early on we were extremely capital constrained, which meant almost every dollar had to go to product, to inventory. I remember our first logo. We bought it on eBay for $50, and that was the logo that went on the first bike. We used it for a couple of years.
I did everything I could early on to make sure as much of that initial capital as possible went toward inventory. Then it was about compounding it: take what I made on the first batch of bikes, buy more on the second batch, keep doubling down. I couldn’t take a salary or bring anyone on, because any money spent on anything else meant our working capital wasn’t growing. It was very important to me to retain equity, even if that meant growing slower and having some out-of-stock periods. In hindsight, I’m happy with that decision.”
Interviews have been condensed and edited for clarity and flow.
*Survey conducted by The Harris Poll on behalf of Shopify from May 25th- June 8th, 2026, among business owners and senior decision makers in the United States, Canada, the United Kingdom, Australia, and France.