Hey Friends -
I don’t know about you, but I’m one of those people who, when I fuck up, I gnaw on it. Over and over. I ruminate. I spiral. I obsess about what I could’ve done differently —not just in a helpful, constructive way, but in a way that sometimes makes things worse.
I’ve gotten better at it, for sure. But it’s still something I have to check myself on.
I wish I were one of those people who genuinely saw failure as a non-event.
A “meh, moving on” kind of person.
Aspirationally, yes. In practice? Not quite.
Even though failure really can get you closer to success. Not just because of what you learn, but because it toughens you up. You build resilience. You get sharper instincts. You start caring a little less about what other people think, and that gives you space to try bigger things.
Sometimes failure is even a sign that you’ve outgrown something. That you’ve reached a new stage. That your old ways of doing things won’t cut it anymore. First-world problems, yes… but also next-level problems.
And realizing you’ve messed up, then being humble enough to admit it and move forward? That’s the kind of growth I actually want.
Which is probably why this week’s episode hit me the way it did.
Jereme Holiman is the co-founder of UrbanStems, a flower delivery startup that scaled fast, raised a bunch of money, and then completely blew it on Valentine’s Day. Like, 1,500 missed deliveries level of blowing it.
That moment ended up changing everything. It forced Jereme and his co-founders to step back and ask, are we still the right people to be leading this?
Jereme’s path into startups wasn’t exactly typical, but it also wasn’t a fluke. He’s one of those people who’s always been curious, sharp, and low-key scrappy in the best way. The kind of founder who didn’t set out to follow some perfect playbook, but still found himself building something that really worked.
In this episode, we talk about:
Hitting the limit of your own skills and being humble enough to admit it
Imposter syndrome (yes, even for guys who’ve raised money and built companies)
Finding the right co-founders and building startup teams
Why founder-led sales is the way to go
The weird identity shift of stepping out of the founder seat
There’s a lot in this one.
About messing up, yes. But also about what it means to still be a builder, even when your role changes.
Even when things didn’t turn out exactly the way you planned.
Hope you give it a listen. I think you’ll get something out of it.
Happy fucking up!
M.
🎧 Prefer Spotify or Apple? Take it to-go:
(And while you’re there - don’t forget to hit subscribe and leave a rating 😁)
✨ About Jereme Holiman:
Jereme Holiman is a multi-time venture-backed founder, early-stage operator, and angel investor. He’s built and scaled startups across fintech, e-commerce, and Web3—including co-founding Clyde Technologies and UrbanStems—and currently serves as VP of People at Shardeum, a Layer 1 blockchain project. Jereme brings a unique perspective to team building, operations, and early-stage growth, and is passionate about supporting founders through the messy middle of building something great.
🧠 What’s Been On My Mind
Playing House: Why Entrepreneurs Build While Wantrepreneurs Perform
I’ve been thinking about this one a lot. It’s about the difference between actually building something and just performing like you are. And honestly… sometimes I wonder where I fit in that. I don’t call myself an entrepreneur. I don’t think I’ve founded anything, not really. Even if I have this podcast. Even if I teach entrepreneurship. Even if people invite me to speak on the topic. I still feel like maybe I haven’t done the thing.
This piece doesn’t give answers, but it definitely got me thinking.
Read →
Living in My Mind Rent-Free
This tweet from Adam Grant hit me in that “ugh, yes, unfortunately” kind of way. It gets at something I’ve been circling around in this episode and honestly... in life. Especially when it comes to imposter syndrome, humility, and all the messy in-between stuff we don’t always talk about.
What do you think?
💐 Just For Funsies
Given the title of this episode, I couldn’t help myself and went down a Reddit rabbit hole looking at 1-800-Flowers fails, specifically the expectation vs reality kind. Here are a few of the ones that had me cracking up:
🦁 More like Lyin’ King. This one gave Mufasa energy, but delivered confused housecat.
🦄 Ordered a unicorn for the proposal. Got a confused chihuahua with a horn.
🐶 It’s a dog. It’s a cloud. It’s... unclear.
I guess the real lesson here is… if it’s shaped like an animal, just don’t.
⭐️ That’s all for now!
Here’s to building, messing up, and figuring it out as you go.
Let me know in the comments what stuck with you from this one.
And if your flower arrangement ever came out looking like a marshmallow dog, please send pics immediately.
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