Steve Wiesner
@SteveWiesnerSMB
Twenty years in IB and mid-market PE. Sharing my journey to scale a fast-growing B2B negotiations training and advisory firm. Proudly 🇨🇦 | 🇺🇲
MY SMB JOURNEY: ~9 yo: Put on a KISS cover-band concert in my basement, sold tix to fam. Modest success. Learned I had absolutely no future in music. ~15yo: Started driveway sealing biz in HS. Made a few grand in a summer. Success. ~16yo: Got job pulling staples out of…
I'm immediately skeptical of people who say they are "First Principles" thinkers.
This is brilliant
Waymo spent 15 years getting from 90% to mostly autonomous. Companies are about to learn the same lesson..
Watching CNBC for the first time in a while. It's a non-stop party. No wonder the market's at an ATH. Seems like there's zero risk in the market right now, based on the talking heads. Someone just said there's "nothing rampant" in terms of speculation around AI, crypto, etc.…
Want to know why AI is a long way away from killing high-end professional services jobs? Let's be real this time. When I was an Associate, I got lectured for a typo on page 52 of a 100 page deck. Pretty much rolled my eyes. "If there's a mistake on page 52, how do we know there…
Elon nuking 80% post-acquisition was an eye-opener far beyond tech. C-Suites are pushing hard to justify any new hires. a) Are they needed? b) Can we outsource / offshore? c) Can AI reduce or eliminate the need for a hire? Hard out there for a lot of folks, and getting harder.
know a lot of extremely talented people who have been unemployed for 6+ months companies doing 8 rounds of interviews, ghosting applicants left and right even if AI is not doing anyone’s job today, it is certainly having an impact on headcount expectations for the near future
Despite growing up middle class, by the time I was 30 yo, I owned a house in Beverly Hills, drove sweet cars, and, according to my proud Dad, "was set for life..." Didn't quite work out that way. 😂😬 👇 Ten(ish) years later, I was drawing down my 401k and moving money from a…
AI is going to 🩸mvrder 🩸IB analysts / associates. Let's see how good GPT is at putting 💄 on a 🐷. Prompt: "Let's assume The Colbert Show is a business, and revenue is down 30% over the past five years despite rising costs. How would an investment banker selling the…
Honest question. 2.5mm people watch Colbert? Who are these people? What's the demographic of a Colbert viewer? Or any "Late Night" show these days? 🤷♂️
Key to a great attitude: whenever something bad happens, force yourself to say: "Well, the good news is..." Car broke down and I had to take it to a shop far from home. 😬 "Well, the good news is, my son and I got to make some cool stops driving to pick it up..." 1. Quality…
This is a HUGE milestone for us. We're expanding our footprint in Asia with the launch of a New Delhi office. When we acquired Watershed almost three years ago, we knew international was a big focus. Now, we're executing. 🚀🚀🚀 🇮🇳🇮🇳🇮🇳 businesswire.com/news/home/2025…
The cold hard SMB truth. If you're the owner, you need to be ready to also be: 1. The accounting guy 2. The sales guy 3. The marketing guy 4. The HR guy 5. The IT guy 6. The legal guy 7. The procurement guy 8. The customer service guy 9. The fundraising guy (hopefully not) 10.…
When you look back on your life on your very last day, what's the one thing you'll be most proud of?
I got my a$s handed to me on my first hot 50k attempt. Badly. What did I prove to myself when I got it done a couple months later? When I get my a$s kicked, I get up and try again. Applies in life, applies in business. One foot in front of the other.
Had lunch w/ a banker whose son got his MBA from Stanford and just closed on a business. He was shocked how many of his GSB classmates didn't have a job lined up. Here's what I tell my sons: don't assume the path that worked brilliantly 20 years ago will work today. It won't.
For those who bought a business a couple years ago, what part of the journey has been most rewarding? For me, an unexpected one. It makes me very happy to know I facilitated a great exit for my sellers. Great people, enjoying every minute of retirement. They earned it.
The Airport Test. Work with people you'd be happy chilling at the airport with when your flight gets delayed. Every single person at Watershed passes that test. EVERY SINGLE PERSON.
Your network fizzles fast when you leave IB / PE. Had lunch today w/ a banker I spent a lot of time w/ during my last PE gig. Hadn't seen him in almost a decade. Was great to reconnect. You'll need to work hard to stay in touch when you're an entrepreneur. It's not easy.…
This stat is remarkable (and potentially understated IMO). My deli added a 3% credit card surcharge. The waitress told me business has been soft ever since. It’s the SMB nightmare scenario. The owner's not being greedy: he's just trying to claw back margin points killed by…
A $100,000 salary in January 2020 has the same buying power as $124,353 in April 2025, according to the U.S. Bureau of Labor Statistics
Wildly underrated movie.
In the last 25 years, Guy Ritchie has yet to make a film better than Snatch. A copy of this on VHS floated around my basement for years & I’ve constantly revisited this film ever since. I think the entire ensemble here is fantastic & it’s Brad Pitt at his absolute goofiest.