Today, let's talk about when is the right time to start a business.

In 2016, I was living in San Francisco, between projects and hungry for inspiration.

I got invited to a well-known VC's house in Atherton a suburb of SF (and the most expensive zipcode in the US). This house must have costed $30M+. The backyard sprawled like a football field, every blade of grass manicured to perfection.

I spotted a friend in the crowd who worked at Apple. A serial entrepreneur with multiple exits under his belt, but he'd been at Apple for five years.

I shared my idea about starting a social app.

He leaned in, his expression a mix of pity and concern. "Look, I'm in the trenches at Apple. I see the numbers. Facebook is swallowing everything. Instagram, WhatsApp - they're all Facebook now. The last independent social app to make it big was Snapchat, and that was five years ago. The window's closed."

When I asked about his own plans, he sighed. "You've got to think in cycles. We're in a downturn. User acquisition costs are skyrocketing. VC money's drying up. Smart money's waiting it out. Maybe in a couple of years, but not now."

I left feeling gutted. This guy had insider knowledge. If he was battening down the hatches, shouldn't I?

On the train ride home, doubt gnawed at me. But then I remembered a Phish concert I attended in Saratoga Springs back in 2006.

It was 2009 and I was attending my first show. The parking lot was a sea of veteran fans, all telling the same story: "Kid, you missed it. The '97 tours, New Year's '95 at Madison Square Garden - that was peak Phish. It'll never be that good again."

I almost sold my ticket. Why bother if the best was behind us?

But I went in. And for three hours, I experienced pure magic. The energy, the improvisation, the connection between band and audience - it was electric. This wasn't a pale imitation of past glories. This was living, breathing, evolving art.

What was that fan that I met earlier smoking?

The next morning, fueled by that memory, I registered my company, Islands.

Nobody gets to decide when the good old days happen. Not for Phish. Not for startups.

Since that conversation, we've seen:

Figma (2016) - valued $12.5B+

Robinhood (2017) - valued $18B+

Notion (2018) - valued at $10B+

Snowflake (2018) - valued at $37B+

You get the idea. He was wrong.

And if you're working about my company Islands. Well, we sold the business. From the proceeds, my team bought houses. They didn't buy private jets or mansions, but they did pretty well.

This is what I'm getting at...

The good old days are now.

It's never a bad idea to ship.

You don't need to go all-in. Start small. Take it step by step.

But above all, start.

Because in five years, someone's going to say 2024 was the perfect time to launch a business.

And you know what? They'll be right.

New Startup Ideas Podcast (SIP) episode🧃 I spoke with Chris Koerner who owns 8 RV parks + 7 companies, as we jam on 5 ideas he would start tomorrow: ​Apple Podcasts, YouTube, Spotify​

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Next up, bookmarks I saved this week worth reading

#1

Joe Kennedy @joekndy “Design Engineer” is a transitional role that we’ll laugh at in 3 years max “Designer” will be someone fully responsible for the frontend “Engineer” will architect the system and solve hard technical problems 3:4 PM • Aug 27, 2024 16 Retweets 377 Likes Read 33 replies

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"Design engineer" is the latest buzzword in Silicon Valley for designers who code. But as Joe noted, this term will likely disappear as the role of designers continues to evolve from what it was just a few years ago.

#2

Founder Confessions @FoundersReveal Jensen Huang's LinkedIn is an absolute flex. 4:34 PM • Aug 26, 2024 398 Retweets 9764 Likes Read 53 replies

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Legend.

#3

Melinda B. Chu @MelindaBChu1 @gregisenberg Nice to see that you’re on the extreme of the Bell Curves of this meme; me too. 😆 GREG ISENBERG @gregisenberg i'm always adding to these open iOS notes: - startup ideas - m&a dreamlist - startup names - interesting phrases - i should remember this - content ideas - goals this week - unpopular opinions - epiphanies - unanswered questions - life hacks - stories highly recommend 12:52 PM • Aug 26, 2024 0 Retweets 6 Likes Read 1 replies

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I'm convinced Apple Notes is the best note taking tool. I used everything, finally back to Apple Notes and my life has been way more productive.

#4

Rohit Mittal @rohitdotmittal Truepill was acquired for a $525M total consideration as reported by Axios (link in next post). But seems like no one made any money. Truepill's no-background: It raised $370 million total from tier 1 investors like Initialized Capital, Oak HC/FT, Optum, and Optum Ventures. The… https://twitter.com/i/web/status/1827346243825041413 10:4 AM • Aug 24, 2024 24 Retweets 441 Likes Read 24 replies

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Truepill got acquired for $525 and founders/team made $0 from this acquisition. Founders didn't sell anything in secondary and the CEO/co-founder was pushed out of his job. Wild to think about a founder who built a $1.6B business (at peak) got nothing from the transaction.

Thanks for reading Greg's Bookmarks.

Thank you for reading Greg's Letter. I hope you found it valuable.

And don't forget to subscribe to my YouTube if this gave you any value. You'll get free startup ideas every few days.​

My goal is to get your creative juices flowing.

Until next week.

Be well,

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