The Incredible Double Interview: Superhuman and Robinhood | E2090

This Week in Startups

Jason Calacanis

Technology

4.4 • 1.3K Ratings

🗓️ 27 February 2025

⏱️ 99 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Today’s show: Jason interviews Rahul Vohra, CEO and founder of Superhuman, and Vlad Tenev, CEO and co-founder of Robinhood. This is a packed episode featuring founder tips, fun stories about how Superhuman and Robinhood got their start and much more!

Timestamps:

(0:00) Episode teaser(2:13) Product market fit and founder journeys(3:25) Jason's investment in Superhuman and market positioning(5:14) AI's role and features in Superhuman(10:25) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist(14:37) Targeting users and competitive advantages(22:23) Evolution and new features of Superhuman

(20:52) Northwest Registered Agent. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!

(24:37) Tackling spam with Superhuman's AI

(27:05) Custom auto labels and email classification

(29:47) Vapi. Go to Vapi.ai and use code Twist200 to get $200 in credits

(32:03) Superhuman's auto reminders and drafts

(34:14) Vlad Tenev and the origins of Robinhood

(39:31) Product design philosophies of Robinhood and Superhuman

(49:29) Scaling design principles and investment decisions(

52:31) Subjectivity in product design

(55:14) Customer feedback in product development

(1:00:00) Superhuman's subscription model and customer acquisition

(1:05:11) PR strategies and news hijacking

(1:12:06) Investment experiences with Robinhood

(1:13:35) Navigating company valuation fluctuations

(1:15:03) Influences on Vlad Tenev and new Robinhood desktop product

(1:22:02) Company resilience and employee reorganization

(1:25:52) Crypto regulation and startup mentality

(1:30:05) Investment trends among Robinhood users

(1:31:12) Retail benefits for startups and capital raising challenges

(1:34:04) Accreditation for private investing and solutions

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Links from this episode:

Check out Superhuman: https://superhuman.com/

Check out Superhuman’s blog post that details all of the new features Rahul went over in the demo: https://blog.superhuman.com/the-next-superhuman-ai/.

Check out Robinhood Legend: https://robinhood.com/us/en/legend/

Article “How Superhuman Built an Engine to Find Product Market Fit”: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/

Check out Rick Rubin’s book: https://www.amazon.ca/Creative-Act-Way-Being/dp/0593652886

Article on Bezos and Washington Post: https://www.newsweek.com/bezos-makes-big-change-washington-post-opinion-focus-endorsed-musk-2036618

Media Bias Chart: https://www.allsides.com/media-bias/media-bias-chart

Check out “Working Backwards” book about Amazon insights: https://www.amazon.ca/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

Check out Rahul’s article on acquisition: https://www.linkedin.com/pulse/rip-mailbox-founders-how-stop-worrying-love-being-acquired-vohra/

Follow Rahul:

X: https://x.com/rahulvohra

LinkedIn: https://www.linkedin.com/in/rahulvohra/

Follow Vlad:

X: https://x.com/vladtenev

LinkedIn: https://www.linkedin.com/in/vlad-tenev-7037591b/

Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

Thank you to our partners:

(10:25) Lemon.io. Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist

(20:52) Northwest Registered Agent. Get more privacy, more options, and more done—visit northwestregisteredagent.com/twist today!

(29:47) Vapi. Go to Vapi.ai and use code Twist200 to get $200 in credits

Transcript

Click on a timestamp to play from that location

0:00.0	Tell him the story. This is the, this is what I knew I invested in the right guy.
0:04.8	We used to onboard every single person in person. And I did the first several hundred myself,
0:10.2	including Jason. The very first thing I did when I sat down with Jason and all these other folks
0:14.7	was, uh, so as a reminder, this is a paid product and no one gets it for free, especially not investors.
0:22.3	That's how I'm going to keep this intellectually honest here on your feedback.
0:26.4	It was like, what?
0:27.4	And I was like, yep, time to pull out your credit card.
0:29.6	Here's a little strike payment form.
0:31.5	But it didn't please.
0:32.4	And I sat there watching him in his credit card.
0:35.0	I did that hundreds of times.
0:36.7	It was so great. Can you imagine you're the first investor in the company? He's, it's a year
0:42.5	later and he's finally ready to show it to me. So you log in and I'm over the shoulder. And he's
0:47.4	like, okay, now you take out your credit. You put it. And I was like, no, no, you actually put your credit card in. It's a dollar a day. It's $365 a day. And I'm like, it's kind of expensive. I was like, you know what?
0:58.4	A moment of truth. This thing better save me a fucking hour a day on my email.
1:03.5	This weekend startups is brought to you by lemon.io. Get access to lemon hire a platform with more than 80,000 pre-vetted engineers that you can
1:11.6	interview within 48 hours. Get $2,000 off your first hire at lemon.io slash hire today.
1:17.4	Northwest Registered Agent. Starting your business should be simple. With Northwest
1:20.9	Registered Agent, you can form your entire business identity in just 10 clicks and 10 minutes. From LLC to
1:26.1	trademarks, domains to custom websites they've got you
1:28.5	covered. Get more privacy, more options, and more done. Visit northwest registered agent.com
1:33.2	slash twist today. And VAPE. Add real-time AI-powered voice conversations to your apps or
	...

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