Feb 14, 2024 · 53m · startup-ideas
The Co-Founder Of A $75M+ Company Gave Me His BEST Business Ideas
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Morning Brew co-founder Alex Lieberman joins host Greg Isenberg to break down actionable, high-margin business opportunities spanning distressed media revivals, creator newsletter partnerships, peer accountability communities, and taste-driven curation platforms.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 27.8% of the talking time here. How this is scored →
Greg as informed peer 6.3 Guest teaching 4.1 Guest disagreement 1.6 Greg pushing back 3.0
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 4:09 Alex rejects romanticizing legacy brand equity over list economics
Alex pushes back directly on Greg's romantic view of brand equity, arguing that paying seven-figure licensing fees from day one is irrational compared to buying raw email assets.
Hardest push from Greg ▶ 3:26 Greg challenges Alex on abandoning the Sports Illustrated brand nameGreg stops the conversation to question Alex's willingness to ditch the iconic brand equity and solely buy the subscriber list, challenging his usual brand-builder identity.
Biggest teaching moment ▶ 16:26 Alex breaks down the Sushi by Boo hotel lobby arbitrageAlex introduces the mechanics of Sushi by Boo's zero-rent rev-share framework in hotel lobbies, teaching Greg a non-obvious business model that inspires the rest of their media strategy discussion.
Greg holds their own ▶ 25:05 Greg refutes assumptions with 11-year search trend dataGreg demonstrates commanding domain expertise by citing 11 years of Google search trend data to disprove Alex's premise that general interest in dieting and weight loss terminology is growing.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Reviving Sports Illustrated Through Email Acquisition and Visual Newsletters | 6 | 4 | 3 | 5 | Greg actively challenges Alex's thesis about buying just the email list instead of licensing the iconic Sports Illustrated brand name, calling him out as usually being a brand romantic. Alex defends his financial pragmatism regarding licensing costs, while Greg brings in concrete data about Authentic Brands' $21B revenue and offers a visual newsletter angle. | |
| Scaling Creator Newsletters Using the Epic Gardening Revenue-Share Model | 5 | 5 | 1 | 3 | Alex educates Greg on Epic Gardening's backend monetization through seeds and wholesale commerce, outlining a playbook for rev-share newsletters. Greg probes why Alex has not executed this himself, framing the bottleneck as content fulfillment versus growth distribution. | |
| Acquiring Distressed Legacy Media and the Sushi by Boo Framework | 6 | 5 | 1 | 2 | Alex shares the novel Sushi by Boo hotel lobby rev-share framework as an analogy for distressed media monetization, which Greg immediately validates. Both hosts build collaboratively on cold-outreach playbooks and taking advantage of the macro advertising downturn. | |
| Modernizing Weight Watchers and Peer-Driven Accountability Challenges for Millennials | 7 | 4 | 2 | 4 | Greg displays strong domain expertise from working with Weight Watchers at his agency and counters Alex's assumptions with 11-year Google search trends data showing declining interest in traditional dieting terms. Greg introduces counter-positioning tactics like community challenges against GLP-1 weight loss drugs. | |
| The Evolution of Peer Groups, AA Frameworks, and Tech Addiction | 7 | 4 | 2 | 3 | Alex discusses tech addiction peer groups and SoulCycle's new concept Peoplehood, but Greg one-ups him with firsthand insider knowledge from attending the earliest Peoplehood beta tests in 2019. Greg also humorously points out the irony of holding virtual Zoom meetings for internet addiction. | |
| Personality-Driven G2: Curated Software Stacks and B2B Affiliate Models | 6 | 4 | 1 | 2 | Alex outlines the B2B affiliate potential of combining Kit.co and G2 for tech stacks, citing a founder making $40k/month from a simple Google Doc. Greg supports the thesis by contrasting high B2B ACVs against low-yield consumer creator views. | |
| Pinterest for Knowledge: Monetizing Taste, Curation, and Inspiration Libraries | 7 | 3 | 1 | 2 | Alex explains his vision for curation as a service, and Greg demonstrates strong industry chops by citing his past background at StumbleUpon and sharing his exact rubric for assessing hiring taste. Greg also pulls up live unit economics and subscriber figures for Really Good Emails. |
Statements from this episode (13)
Lieberman: A massive Morning Brew-style daily sports newsletter remains unbuilt
“I don't think there's like the go-to daily sports newsletter that And I think to have a head start with Sports Illustrated's list, whether or not I would even have to use the brand, like, it's actually kind of irrelevant to me. Like, if I could just get the li…”
Lieberman: Legacy media operators underestimate media as top-of-funnel acquisition
“I think a lot of people in like old media don't understand the Kind of the value of attaching a media brand to a non-media company to provide top of funnel for it.”
Lieberman: Epic Gardening makes most revenue from product sales, not ads
“Actually the way they make the majority of their money is through product sales. Kevin and Epic Gardening bought a seed company that they sell through their channels, and so they do both direct-to-consumer, but they also sell their seeds wholesale”
Lieberman: 3M YouTube subs should convert to 500k email subscribers quickly
“They have three million YouTube subscribers. Like you should be able to get that list to 500,000 subscribers quickly.”
Lieberman: Distressed legacy media ignored newsletters as destinations, creating opportunities
“I think any legacy media brand that stands for something that is cutting head counter staff at bare minimum and closing their doors at maximum,
Is an opportunity for this because I still have yet to meet a legacy media company that truly thinks about their new…”
Lieberman: Sushi by Boo expands rent-free in hotels via 20% rev-shares
“Every sushi by boo is in a hotel and they go to a hotel and they say, Hey hotel, let's say your lobby is 3000 square feet.
See the, see those 250 square feet in the corner of your lobby that right now has a chair and maybe a chess table.
Let us build a sushi b…”
Isenberg: Proprietary branded terminology creates a highly defensible moat
“When you own these terms, it's a moat that is very, very defensible.”
Lieberman: Community builders should study Alcoholics Anonymous and read the Big Book
“AA is just a model for anyone who is interested in community building and group dynamics, like, should just read the big book and study AA's history”
Lieberman: Businesses targeting loneliness are much harder than tangible outcome businesses
“Like you see all these studies around loneliness in society, and I do believe it, but I also think it's way harder to build a great business off of that because it's always less tangible. It feels more ephemeral. You want to join a dieting program, you very cl…”
Lieberman: G2's business model is broken due to sponsored listings
“So I mean, I think the reason is one is like the business model is inherently broken, like, because it thrives off of like sponsored posts and sponsored listings. There's just this inherent question about the authenticity of the recommendations.”
Lieberman: DTC founder earns $40K monthly from software affiliate Google Doc
“There's an entrepreneur I know, and I don't know if he wants people to know this, so I'm not going to say who it is, who built a popular direct to consumer company, sold this company, and he has found a way, he has manually built his stack. So he created a Goo…”
Lieberman: Taste is one of the greatest advantages amid tech commoditization
“In a world of hyper-commoditization, where software's commoditized, where content's being commoditized, where like many things are becoming where we are being displaced
By technology, I think taste, like having, being an incredible taste maker is actually on…”