I sat down with my wife Jessie for a really special episode of the podcast. We talked about what it’s actually like being married to a serial entrepreneur, the highs, the lows, and all the uncertainty in between. I asked her how she’s managed to stay supportive through all the pivots, experiments, and tough seasons. We got honest about what it’s really been like building a life together while also building businesses. Whether you're an entrepreneur yourself or you're married to one, I think this one will hit home.

Timestamps below. Enjoy!

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00:00 Overcoming Overwhelm in Entrepreneurship
03:02 The Role of a Supportive Spouse
05:56 Navigating Scary Moments in Business
08:49 Trust and Confidence in a Partner
12:12 Advice for Spouses of Entrepreneurs
15:07 Balancing Family and Business
17:56 Reflections on Stability and Sacrifice
20:49 Key Conversations in Marriage
24:08 Parenting as Entrepreneurs
27:01 Compartmentalizing Work and Family Life
29:55 Maintaining a Strong Marriage
32:49 Future Aspirations and Business Dreams

I sat down with Tyler Denk (@denk_tweets), cofounder and CEO of Beehiiv, to talk about the biggest opportunities to make money with newsletters right now. Tyler shared how small niche newsletters are making serious revenue by focusing on community and creative monetization like design cohorts, recruiting, and smart sponsorships. We talked about growth strategies like Beehiiv Boost, co-registration, and why acquiring the right subscribers matters more than just getting them cheap. We ended with a killer idea: turning a corporate email list into a media business that brings in sponsorship revenue.

Use code OFFICE20 for 20 percent off your first 3 months on Beehiiv, and if you want to support the show, here’s my partner link: https://beehiiv.com?via=chris-koerner-BH-COLLAB

You can subscribe to Tyler’s newsletter Big Desk Energy at mail.bigdeskenergy.com, and check out his Spotify playlist of the same name if you're into deep focus work sessions.

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Watch this on YouTube instead here: tkopod.co/p-yt
Ask me a question on or off the show here: http://tkopod.co/p-ask
Learn more about me: http://tkopod.co/p-cjk
Learn about my company: http://tkopod.co/p-cof
Follow me on Twitter here: http://tkopod.co/p-x
Free weekly business ideas newsletter: http://tkopod.co/p-nl
Share this podcast: http://tkopod.co/p-all
Scrape small business data: http://tkopod.co/p-os
---

00:00 The Gold Mine of Email Lists
02:58 Monetizing Newsletters: Strategies and Insights
06:13 The Power of Local Newsletters
09:04 Building a Community Through Content
11:53 Experimentation and Growth Strategies
15:06 The Future of Local Newsletters
17:54 Creating Value Beyond Sales
21:10 Referral Programs: The 80/20 Rule
23:58 Transforming Email Lists into Revenue Streams

I sat down with Frey Chu (https://x.com/freychu), who started by building profitable directory websites and later began teaching others how to do the same. We talked about how he went from flipping items at flea markets to pulling in up to $3,000/month in passive income from sites he barely touches. He broke down his process for finding untapped SEO opportunities, how he uses Ahrefs and Reddit for research, and shared a realistic approach to building simple, mostly passive websites that can steadily bring in income over time.

Timestamps below. Enjoy!

---
Watch this on YouTube instead here: tkopod.co/p-yt
Ask me a question on or off the show here: http://tkopod.co/p-ask
Learn more about me: http://tkopod.co/p-cjk
Learn about my company: http://tkopod.co/p-cof
Follow me on Twitter here: http://tkopod.co/p-x
Free weekly business ideas newsletter: http://tkopod.co/p-nl
Share this podcast: http://tkopod.co/p-all
Scrape small business data: http://tkopod.co/p-os
---

00:00 The Power of Simple Solutions
03:12 Opportunism and Business Growth
06:01 Navigating Online Criticism
09:23 The Nature of Selfishness in Business Relationships
12:16 Stress Management and Decision Making
15:09 The Role of a CEO
18:03 AI in Business Efficiency
21:54 The Impact of AI on Employment
25:18 Navigating Wealth and Parenting
31:53 The Reality of Entrepreneurship
36:15 Business Ideas and Getting Started
42:03 The Book Writing Journey