Dec 28, 2023 · 35m · startup-ideas
My Biggest WINS & REGRETS Of 2023
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In this comprehensive 2023 year-in-review, entrepreneur Greg Isenberg delivers an unfiltered breakdown of his personal milestones, business wins and losses across his Late Checkout holding company, audience growth metrics, net worth asset allocation, and productivity frameworks.
Statements from this episode (17)
Isenberg: Late Checkout acquired 50% of BoringMarketing.com as first acquisition
“Another big win is we bought 50% of a business which became BoringMarketing.com, which is basically an AI enhanced SEO business, so it's some tools that help companies get organic search, and that was our first real acquisition.”
Isenberg: BoringMarketing.com will generate $2M–$3M free cash flow in 2024
“The crazy thing is, by next year, or in 2024, I should say, the business conservatively will do two to three million dollars of free cash flow.”
Isenberg: Late Checkout and all portfolio businesses were profitable in 2023
“The other big win was we produced nice cash flow for late checkout which is our holding company. And we continue to grow several cash flowing businesses, which is awesome. So the hold co made money, all the individual businesses made money.”
Isenberg: Late Checkout rejected a $30M private equity investment offer
“Another big win is someone offered us and not just someone, someone I really, really respect and a top tier investor offered us. Thirty million dollars of private equity capital to scale out late checkout. We didn't take it, but it did feel quite good.”
Isenberg: Late Checkout lost $3M+ in 2023 revenue by staying lean
“We basically had full utilization of our team the entire year, and we lost at least three million dollars of revenue. If we just would have not listened to this advice, we would have had three plus more million dollars in the bank.”
Isenberg predicts a huge wave of holdco 'multipreneurs' over five years
“I think there's going to be a huge wave of successful multipreneurs over the next five years, just like over the last couple of years, you start to see the wave of solopreneurs all over.”
Isenberg claims premium .com domains significantly boost B2B conversion rates
“Until I saw how much of an increase in conversion rate you can get when it comes to a great dot com, especially in B to B. So I've seen this a few times in 2023, and I'm starting to think that premium domains are undervalued some of them.”
Isenberg's startup heuristic: marry the niche, date the product
“Marry the niche, date the product. So what that means is you can give up on a product, but don't give up on the niche you believe in. So it's common for your product to fail.”
Isenberg prioritizes Canadian hiring to leverage 35% currency discount
“We hired some exceptional Canadians in twenty-twenty-three and I want to do more of it. Obviously continue to still hire in the US, but only for select high impact roles because I'd love to save that 35% and put that into a premium domain or put that into mark…”
Isenberg says Late Checkout is actively acquiring community-based businesses
“So if you're selling your agency, your marketplace, your email newsletter, your vertical SaaS, your social network, get in touch with me. We're buying community-based businesses.”
Isenberg: Newsletter doubled to 72,000 subscribers in 2023 without paid ads
“On my newsletter in January, twenty-twenty-three, I had 36,000 subscribers. Today I have 72,000 subscribers, so pretty good. But I didn't spend any money on advertising.”
Isenberg: Podcast had zero download growth between 2022 and 2023
“20, 22. I had 360,000 downloads in 20, 23. I had 360,000 downloads. So there's been no growth”
Isenberg: First ideas are irrelevant catalysts; the second idea is what matters
“Over the years. I've learned that the first idea you have is irrelevant. It's just a catalyst for you to get started. Then you figure out what's wrong with it. And you go through phases of denial, panic, regret, then you finally have a better idea. And the sec…”
Isenberg: Repurposing tweets grew his LinkedIn from 10k to 82k followers
“LinkedIn a year ago, I had 10,000 followers. Now I have 82,000 followers. I'd been sleeping on LinkedIn. And I had already been writing tweets for years. So yeah, what I basically do is I take my tweets and I put it on LinkedIn.”
Isenberg: Trimmed Google stock position to reallocate into Microsoft
“I had a bigger stake in Google and trimmed it a little bit. Roy, Royal Bank, and I trimmed it because of And put it into Microsoft basically.”