What are the key takeaways from this How I Built This episode?

Key insights include: **Earned Growth Framework:** Berkowitz argues that brand awareness metrics in each geography should gate expansion speed. Insomnia opened too many locations too quickly in certain markets before consumer love was established. Founders should monitor awareness data by region and only accelerate when local demand signals — not internal ambition — justify the next wave of openings.; **SKU Reduction Strategy:** Across cookies, cupcakes, and frozen yogurt, Berkowitz found that cutting product lines down to three to five proven bestsellers outperformed broad catalogs. For early-stage brands like Kahindo, identifying which specific products drive the most revenue and occasion-based purchases creates a focused foundation for wholesale pitches and targeted marketing spend.; **In-Person Demonstration Over Paid Ads:** For products requiring consumer education — sauna hats, specialty fashion — live demonstrations outperform Meta and Google ads. Berkowitz notes that customer acquisition costs on paid channels are high and rising. Pop-ups, wellness fairs, spa placements, and ambassador programs generate lower-cost conversions when the product's value proposition requires tactile or visual explanation.

What did Seth Berkowitz Of Insomnia discuss on How I Built This?

Insomnia Cookies founder Seth Berkowitz joins Guy Raz on the How I Built This Advice Line to counsel three early-stage founders — a luxury fashion brand, a sauna hat company, and a collegiate stadium bag business — on customer acquisition, product focus, and sustainable growth strategy. Key topics include: **Earned Growth Framework:** Berkowitz argues that brand awareness metrics in each geography should gate expansion speed. Insomnia opened too many locations too quickly in certain markets before consumer love was established. Founders should monitor awareness data by region and only accelerate when local demand signals — not internal ambition — justify the next wave of openings.; **SKU Reduction Strategy:** Across cookies, cupcakes, and frozen yogurt, Berkowitz found that cutting product lines down to three to five proven bestsellers outperformed broad catalogs. For early-stage brands like Kahindo, identifying which specific products drive the most revenue and occasion-based purchases creates a focused foundation for wholesale pitches and targeted marketing spend..

How long is this episode of How I Built This?

This episode is 43 minutes long. SignalCast provides an AI-generated summary so you can get the key insights in about 3 minutes.

How I Built This

Advice Line with Seth Berkowitz of Insomnia Cookies

October 22, 2026

43 min episode · 2 min read

Seth Berkowitz Of Insomnia

Episode

43 min

Read time

2 min

Topics

Career Growth, Productivity, Health & Wellness

AI-Generated Summary

Published Oct 22, 2026

Key Takeaways

✓Earned Growth Framework: Berkowitz argues that brand awareness metrics in each geography should gate expansion speed. Insomnia opened too many locations too quickly in certain markets before consumer love was established. Founders should monitor awareness data by region and only accelerate when local demand signals — not internal ambition — justify the next wave of openings.
✓SKU Reduction Strategy: Across cookies, cupcakes, and frozen yogurt, Berkowitz found that cutting product lines down to three to five proven bestsellers outperformed broad catalogs. For early-stage brands like Kahindo, identifying which specific products drive the most revenue and occasion-based purchases creates a focused foundation for wholesale pitches and targeted marketing spend.
✓In-Person Demonstration Over Paid Ads: For products requiring consumer education — sauna hats, specialty fashion — live demonstrations outperform Meta and Google ads. Berkowitz notes that customer acquisition costs on paid channels are high and rising. Pop-ups, wellness fairs, spa placements, and ambassador programs generate lower-cost conversions when the product's value proposition requires tactile or visual explanation.
✓End-User vs. Buyer Marketing: When the purchaser and the user are different people — as with Desden's stadium bags, where mothers buy for college-age daughters — Berkowitz advises centering all marketing on the end user. The end user carries the brand socially, generates word-of-mouth, and influences future purchases. QR codes inside products can help collect end-user data directly.
✓Brand Partnerships for Clear-Bag Products: Berkowitz suggests that products with visible, transparent design — like clear stadium bags — create natural co-branding opportunities. Partnering with complementary brands to place products inside the bag gives both parties mutual promotional incentive, generates social content, and builds cultural relevance with the target college demographic at zero additional manufacturing cost.

What It Covers

Insomnia Cookies founder Seth Berkowitz joins Guy Raz on the How I Built This Advice Line to counsel three early-stage founders — a luxury fashion brand, a sauna hat company, and a collegiate stadium bag business — on customer acquisition, product focus, and sustainable growth strategy.

Key Questions Answered

•Earned Growth Framework: Berkowitz argues that brand awareness metrics in each geography should gate expansion speed. Insomnia opened too many locations too quickly in certain markets before consumer love was established. Founders should monitor awareness data by region and only accelerate when local demand signals — not internal ambition — justify the next wave of openings.
•SKU Reduction Strategy: Across cookies, cupcakes, and frozen yogurt, Berkowitz found that cutting product lines down to three to five proven bestsellers outperformed broad catalogs. For early-stage brands like Kahindo, identifying which specific products drive the most revenue and occasion-based purchases creates a focused foundation for wholesale pitches and targeted marketing spend.
•In-Person Demonstration Over Paid Ads: For products requiring consumer education — sauna hats, specialty fashion — live demonstrations outperform Meta and Google ads. Berkowitz notes that customer acquisition costs on paid channels are high and rising. Pop-ups, wellness fairs, spa placements, and ambassador programs generate lower-cost conversions when the product's value proposition requires tactile or visual explanation.
•End-User vs. Buyer Marketing: When the purchaser and the user are different people — as with Desden's stadium bags, where mothers buy for college-age daughters — Berkowitz advises centering all marketing on the end user. The end user carries the brand socially, generates word-of-mouth, and influences future purchases. QR codes inside products can help collect end-user data directly.
•Brand Partnerships for Clear-Bag Products: Berkowitz suggests that products with visible, transparent design — like clear stadium bags — create natural co-branding opportunities. Partnering with complementary brands to place products inside the bag gives both parties mutual promotional incentive, generates social content, and builds cultural relevance with the target college demographic at zero additional manufacturing cost.

Notable Moment

Berkowitz revealed that during Insomnia's most difficult period, investors closed their checkbooks entirely, forcing him to cut his team and go without personal salary for eighteen consecutive months — a detail he says he actively compartmentalizes because the experience was so difficult to process.

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Episode Transcript

Hello, and welcome to the advice line on how I built this lab. I'm Guy Raz. This is the place where we help try to solve your business challenges. Each week, I'm joined by a legendary founder, a former guest on the show who will help me try to help you. And if you're building something and you need advice, give us a call, and you just might be the next guest on the show. Our number is 1804331298. Leave us a one minute message that tells us about your business and the issues or questions that you'd like help with. Alright. Let's get to it. Joining me this week is Seth Berkowitz. He is the founder and CEO of Insomnia Cookies. Seth, welcome back to the show. Pat, it's great to be back. It's great to have you back. You were first on the show, I think, in 2024. And, of course, if if any of you listening have not heard that story, we'll put a link to it in the show notes. Great episode. You got the idea for Insomnia Cookies while you were in college, and you had a craving for, like, a late night treat, and the only options were pizza and Chinese food. You basically started this business delivering fresh cookies from your dorm room to customers, and then eventually, you built a brick and mortar and and and and the rest is history. Insomnia Cookies is is a a a national chain. When when you were last on the show in 2024, you had... Thinking about 300 locations of the stores. And today, you've got closer, I think, to 400. And the goal is to get to 1,800. Is that the number? That's right. Yeah. We're gonna finish the year with roughly 393 bakeries around the world. And that's our major aspiration, right? We want to open up 1,800 bakeries and really be a global chain. And what's the 1,800 number? Where does that come from? Honestly, data dive. We're looking at as as the business scaled from city to college to suburbs to train stations and stadiums, that's what we ended up targeting based on the... We thought could be The US output and then so far what the international opportunity looks like. So that's that's our goal. You... One one of the things that that is is interesting, I think you own and operate the stores. Right? Insomnia owns and operates all their... All your bakeries. We have four licensing arrangements. Airport and three stadiums, beyond... We we operate 390 bakeries around the world. So, basically, you're you're not a franchise business. Right? No. Certainly not. But, of course, franchising could get you to 1,800 a lot faster. Right? And you know that. It could. Of course. Tell me the the thinking behind resisting that that model. I mean, some of it is just how it was... How the system was built. You know, it's a late night delivery collegiate business. Right. …

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