The #1 podcast for entrepreneurs. Learn proven strategies to start and grow a business, improve productivity, and live a happier life. Hear from top performers in all industries. Guests include entrepreneurs, CEOs, consultants, and more.
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Right before I recorded this episode, my daughter was crying because she wanted me to stay and have lunch with her. I don't wanna lie to her. I told her, "Daddy's going to work, and then I'll come back." That's been on my mind a lot lately. This month I'm talking about what it's really like running a multi-million dollar business while raising two young daughters. The guilt, the trade-offs, the…
A listener sent me a message saying I'd lost my spark. That I didn't sound inspired anymore. Honestly... it made me stop and think. In this episode, I unpack why he was partly right. My calling isn't software deals anymore. It's building businesses, solving problems, and showing up for the people who count on me. I also share one AI workflow that's completely changed how I lead AppSumo, why we…
This month I've been thinking a lot about distractions and how easy it is to spend time on things that feel productive while avoiding the one thing that actually matters. I've been getting distracted by stocks and NBA bets, using AI as a weirdly effective therapist after an argument with my wife, and finally the big focus reset we're making at AppSumo. If you've been feeling scattered, stuck, or…
I'm feeding my baby while recording this… she's spilling milk, I'm spilling AppSumo updates . Everybody wins. So we've gone from 140 people down to around 40. Revenue has dropped hard. And for the first time in 16 years, staying in business actually feels uncertain. So this episode is about what we're doing now. What's working, what's not, and how we're getting things back on track. I talk about…
We were spending $56K/year on AI tools at AppSumo. A dozen subscriptions, nobody sharing anything. So we killed all of it and put the entire company on one Claude plan. Let's go. This episode I break down exactly how we rolled out AI to every single teammate in 3 weeks, why the tool itself wasn't the secret (the shared platform we built on top was), and the wild stuff that happened when…
I just turned 44, and we just had our second daughter. Double girl dad. Let's go. This episode is a mix of life lessons, AI experiments, and some questionable investing decisions. I talk about what having a second kid taught me, why self-belief matters way more when revenue is down, and how getting older has made me care less about awards and more about meaning. I also tested OpenClaw, gave it…
I just had lunch with someone who sold a billion-dollar company. What stuck with me wasn't the money, it was how seriously he took standards. Not just in his work but through his entire life. This month I talk about what standards really mean, why they're just values in action, and how raising them creates clarity instead of chaos. This is about doing better work, even when things feel messy, and…
It's New Year's Eve, and I've been taking stock of everything 2025 threw my way and what I want 2026 to look like. There were plenty of ups and downs, but what didn't work has forced me to rethink how I lead. In this episode, I talk honestly about what's changing at AppSumo, what I've learned by getting closer to the work again, and why leadership right now looks very different than it did. In…
Today, I'm giving you part three of the AppSumo saga. Black Friday was rough, targets got missed, and the team felt it. But I zoomed out and the signals actually looked way better than expected. Refunds are dropping, deal quality is rising, customer sentiment is improving, and we're finally stabilizing the business after a horrible year. So in this episode I break down our simple three part plan…
The past few months at AppSumo have been brutal. People are voting with their wallets and return buyers are down 40%. We lost some of the trust we spent years building and drifted from what made us great. But the fire in my belly is back and I'm going to war for what we do best. I'm turning the battleship back towards curating high-quality tools that people actually love and I'm taking you inside…
