What Jeff Bezos can teach us about delayed gratification, reputation, sacrifice and building something worth waiting for
We all know the Amazon of today.
Packages magically appearing on our doorstep. Prime. Whole Foods. AWS. Delivery trucks everywhere. Even Amazon airplanes flying overhead. Basically, the whole nine. It’s hard to imagine a world without it. It’s even harder to imagine that it started in a garage.
In 1994, Jeff Bezos left a successful career on Wall Street (yes, Wall Street) and moved across the country to pursue an idea that, at the time, was anything but a sure thing: selling books on this relatively new thing called “the internet.” His boss actually told him it was a good idea, but perhaps a better idea for someone who didn’t already have a good job.
Ouch.
Bezos thought about it and came back to what he called his “regret minimization framework.” He imagined himself at 80 years old and asked which decision he was more likely to regret.
Trying and failing? Or never trying at all?
He chose the garage.
And let’s be clear, this wasn’t the kind of garage startup that gets romanticized later with a great soundtrack and a billion-dollar ending. Amazon’s early team worked on desks made from doors. Bezos and his small team packed orders themselves. Packages were driven to the post office in the family car. His parents invested a significant portion of their life savings in the company, even after Bezos told them there was a very real possibility they’d lose it.
There was no Prime, no private jets, and certainly nothing resembling overnight success. Mostly, there was just a lot of work. Lots and lots of work. And maybe that’s the part of entrepreneurship we don’t talk about enough anymore. We live in a world where everyone gets to show us the highlight reel… the launch, the new office, the big client, the fabulous trip. The perfectly staged “working from anywhere” photo with a laptop strategically positioned next to a cappuccino. We rarely see much of what happened in between.
Nobody posts the Tuesday night when you’re still working at 12:47 a.m.
My own entrepreneurial journey started 25 years ago, although I can’t exactly say it was all part of some brilliant master plan. A fresh New York transplant, I was a young VP at a Florida agency with a heavy roster of tech clients when the dot-com bubble burst. And the agency… well, it burst too. Suddenly, I was on my own.
So I did what entrepreneurs do. I figured it out. I started working for myself, built from there, and eventually incorporated my company in 2007. I’m not sure I really chose entrepreneurship at that point. It felt a little more like entrepreneurship chose me. Either way, I had to figure out how to make it work.
And I remember those years very well.
I had my daughter Olivia in 2005, and I took two weeks off because I was genuinely afraid that if I disappeared too long, I might lose clients. Seventeen years ago, when I had my son Trevor, I took four days.
Four days.
Looking back, that sounds slightly insane even to me. But one of my biggest clients needed something done, and I felt obliged to do it.
Today, I have a team. I can delegate. I don’t have to personally touch every single part of my business. But that came later. And it took …years. In the beginning, there was no one else to delegate to. And even when there was, I felt uneasy about it.
That’s the part I think gets lost when we talk about successful entrepreneurs. We see the company they eventually built. What we usually don’t see are all the things that happened along the way, including some of the sacrifices they probably wouldn’t make the same way today. And I’m certainly not suggesting everyone needs to work four days after having a baby. Please don’t.
I don’t look back on those years and think exhaustion was some badge of entrepreneurial honor. There are things I’d definitely do differently today.
It’s the delayed gratification piece.
Sometimes you make a sacrifice in the moment because you believe in what you’re trying to build for the future. And while you’re building the business, whether you realize it or not, you’re also building something else: your reputation.
Bezos has famously said, “Your brand is what people say about you when you’re not in the room.”
I’ve spent my career in marketing and PR, and I think that’s one of the simplest and smartest definitions of a brand I’ve ever heard. Because your brand isn’t really your logo, your website or how many people follow you. Those things matter, of course. But your real brand is what happens when someone mentions your name in a room you’re not in.
Do they trust you enough to recommend you? Do they respect your work? And maybe most importantly, would they want to work with you again?
You don’t need to be in business for 25 years to have a brand. You have one from the moment people begin having experiences with you. But after decades of building my own company, I will say there’s something incredibly rewarding about knowing that the reputation you’ve worked so hard to build has become part of the business itself. I’m proud when someone recommends me or speaks highly of my company, not because I think I’ve done everything perfectly (trust me, I haven’t), but because I know how many years it took to earn that trust.
And trust isn’t something you can fake.
There’s a lot of “fake it till you make it” energy in entrepreneurship today. And I’m definitely not a “fake it till you make it” hater. I think most entrepreneurs have at least one good story of their own.
I certainly do.
Right before I incorporated my business, I landed a meeting with P&G.
Yes, that P&G. Procter & Gamble.
I walked into the room and presented a rebranding and packaging concept for one of their hair product lines. I had the experience. I had the credentials. I knew I could do the work.
What I didn’t quite have yet was an established company.
Minor detail.
I gave the presentation, they loved it, and I walked out the door with a $5,000 check made out to my new business. And yes, companies still wrote actual checks back then. It was practically another era.
There was just one small problem.
I didn’t have a business bank account yet. Looking back years later, that still makes me smile. Was I “faking it till I made it”? Maybe a little. But I wasn’t faking the talent, the experience or my ability to deliver. I was simply walking into the room as the entrepreneur I was still becoming. And it worked. P&G became a great client and a great partnership for my young company.
Maybe that’s the difference.
Sometimes “fake it till you make it” isn’t about pretending to be something you’re not. It’s about having the confidence to step into something before you feel completely ready.
So go into the room and give the presentation. Ask for the business even if part of you is wondering whether you’re quite ready for it. Because once they say yes, you actually have to deliver. There has to be something real behind the confidence, and it has to last a lot longer than the Instagram post.
Amazon opened its virtual doors in 1995. Two years later, it went public. What began as an online bookstore eventually changed the way much of the world shops, reads, watches television, stores data and runs businesses. That didn’t happen overnight. It just looks that way when you’re looking backward. Maybe that’s the lesson Bezos’ garage holds for the rest of us.
Don’t be so busy trying to look successful that you forget to build something successful. And don’t be so busy building your “brand” that you forget to build the reputation behind it.
A lot of building a business really is pretty unglamorous. Give the idea time. Make the sacrifices that make sense for your life, not someone else’s (looking back, jumping on a client project four days after giving birth may not have been one of my better moves). Keep your promises. Do good work. And understand that the season when you’re doing everything yourself doesn’t necessarily last forever.
Eventually, if you build it well, you get to delegate.
You get to breathe a little. You might even get an airplane.
I’m still waiting on that one ;).
But first, there’s usually a garage. Or a basement. Or, in my case, a laptop and a dream.
