First Time Founders vs. Second Time Founders

Founder's Journal

Morning Brew

Careers, Business, Entrepreneurship

4.8 • 1.1K Ratings

🗓️ 8 November 2023

⏱️ 24 minutes

🔗️ Recording | iTunes | RSS

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Summary

Episode 65: Alex Lieberman (@businessbarista) chats with Dan Siroker (@dsiroker), a serial entrepreneur who is currently the co-founder and CEO of Rewind, a personalized AI that captures everything you’ve ever seen, said, or heard. Prior, he was the co-founder and CEO of Optimizely, a $500M Martech business doing over $110M in annual revenue. In this episode, Dan takes us through his X series, “First Time Second Time Founder,” where he shares the biggest differences he’s observed in himself as a seasoned entrepreneur vs. when he was a first time entrepreneur. Dan’s posts: Focus: https://x.com/dsiroker/status/1718440871819903309?s=20 Feedback: https://x.com/dsiroker/status/1718024961606975885?s=20 Headcount: https://x.com/dsiroker/status/1717775227243897048?s=20 Investors vs. Users: https://x.com/dsiroker/status/1717732248512790530?s=20 Product: https://x.com/dsiroker/status/1717678664718971034?s=20 Collaboration: https://x.com/dsiroker/status/1717593744399376859?s=20 Send us an email and let us know what you think of the idea! [email protected] Grow more (and stress less) with Brex: brex.com/foundersjournal #FoundersJournal #Startups #Entrepreneur Listen to Founder’s Journal here: https://link.chtbl.com/OV4W93_W Watch Founder’s Journal here: https://www.youtube.com/@FoundersJournal/ Subscribe to Morning Brew! Sign up for free today: https://bit.ly/morningbrewyt Follow The Brew! Instagram - https://www.instagram.com/morningbrew/ Twitter - https://twitter.com/MorningBrew Tik Tok - https://www.tiktok.com/@morningbrew Follow Alex! Alex Lieberman (@businessbarista) Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	What's up everyone? Welcome back to another episode of Founders Journal. I'm Alex Lieberman,
0:04.9	co-founder and executive chairman of Morning Brew. I want to give a huge shout out to
0:09.7	Lindsay L. a Founders Journal listener who finally took the leap of faith to shoot me an
0:13.9	email to say what up our email conversation led to a Zoom conversation and I
0:18.3	learned so much about her industry and how she thinks about being
0:21.4	entrepreneurial within a large firm.
0:24.0	She said it took her 10 Founders Journal episodes to finally muster up the courage to email
0:28.2	me, which means there are a lot of you out there that haven't done so but want to. So what I'm about to say is directed to you. Do not wait. Today is the day that you reach out and we start a conversation. I want to get to know you and your story.
0:41.6	Shoot me an email to Alex at morningbrew.com and tell me a little
0:44.6	bit about who you are and I'll take it from there. Now for today's episode today we are
0:49.2	breaking down some of the key differences between first time and second time founders.
0:53.6	My guest is Dan Siroker, a serial entrepreneur who is currently the co-founder and
0:58.1	CEO of Rewind, a personalized AI that captures everything you've ever seen, said, or heard.
1:05.0	And prior, he was the co-founder and CEO of Optimisley, a 500 million dollar Martek business that does over
1:11.2	110 million dollars a year in revenue.
1:14.0	Dan recently started a series on Twitter that I'll call first time second time founder
1:18.9	where he shares the biggest differences that he has observed in himself as a seasoned
1:23.7	entrepreneur versus when he was a first-time entrepreneur.
1:26.7	He's going to take us through all of his posts in the series as well as a few new
1:30.6	ones he has never shared publicly. Let's hop into it.
1:37.0	Today's episode of Founders Journal is sponsored by Brex.
1:48.0	Brex is a financial stack created for founders by founders that helps startups optimize their finances at every stage of growth.
	...

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