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Joined February 2010
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According to Sam Lessin, about 1% of Slow Ventures’ bets turn out to be fraud. His take: if your seed portfolio has no fraud whatsoever, you’re probably not being creative enough.
Jason, Sam, and fellow VC roundtable experts Paige Doherty and Jenny Fielding argue that diligence has to scale with the check. If you’re giving out $25K or $100K, you don’t have the time or funds for deep diligence. But if you’re writing a $100M check, you can’t afford to skip it.
Hear the panel discuss when a little diligence is good enough and what went wrong with Theranos, FTX, and other infamous disasters on TWiST 2353.
@jason, @lessin, @paigefinnn, @jefielding, @slow, @behind_genius, @EverywhereVC, @Lons
0:00 Our new “This Week in VC” newsletter
2:57 Panel intro: Sam Lessin, Paige Doherty, Jenny Fielding
8:51 Why gambling loses appeal for VCs
11:44 Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at plaud.ai/twist and use code TWIST for 10% off!
17:00 DigitalOcean - Head to do.co/twist to start building on DigitalOcean's AI-Native Cloud today - and cut your AI workload costs by up to 50%
18:17 Best moments from “You Can See Everything”
22:24 Unreliable narrators and unknowable situations
25:23 Living in a post-truth moment
30:44 Due diligence horror stories
33:27 Odoo: The all-in-one business platform. Your first app is free! Get started today at odoo.com/twist
35:32 The VCs remember their fraud investments
39:21 How LAUNCH trains founders to prep for diligence
45:13 How Elizabeth Holmes kept raising money
55:36 Would you invest in an Elizabeth Holmes company?
58:09 Thanks to our partners at Rippling! Head to rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business.
1:03:10 Why seed funds need pro rata rights
1:09:44 When “founder friendly” means rolling over
1:17:07 The three investor relationships: team, founders, LPs
1:21:44 ElevenLabs “Archer” voice controversy
1:27:58 How NIL deals reshaped college sports
1:34:36 Cameo for Business and long-tail celeb endorsements
1:36:33 Portfolio company shoutouts
🎥 Watch the full episode here 👇
OpenAI is reportedly close to raising $30B at a $1.25T valuation. That’s $150B less than the number they were seeking just a month ago, but Jason says “I think they’ve actually right-sized the valuation.”
A year ago, hype pushed the big AI companies’ value to more than 100x revenue. Now, that multiple is far lower, and the businesses are still growing fast.
Would you consider buying OpenAI shares at that valuation, and then holding it for 10 years?
Plus: SpaceX wants to be a major cell carrier, Meta will pay Zuck’s billionaire tax for him, and who watches the AI watchdogs?
@jason, @lons, @finkd, $SPCX, $META
0:00 Jason’s in SF with the LAUNCH Accelerator 37 cohort
3:27 Plaud: If your work depends on conversations - interviews, meetings, calls - you need a Plaud NotePin S. You can check it out at plaud.ai/twist and use code TWIST for 10% off!
7:21 Tactical & Practical talks live at Salesforce Tower
11:08 Using Claude for brainstorming, not writing
20:13 Sentry - New users can get $240 in free credits when they go to sentry.io/twist and use the code TWIST26
21:29 OpenAI closing $30B at a $1.25T valuation
26:51 Why OpenAI could still lose
31:12 Would you put 30% of your retirement into OpenAI?
33:21 Lightfield - Name one person who's ever enjoyed updating a CRM. Exactly. Lightfield's AI agent does it for you - it even prospects and books your meetings. Used by thousands of startups. Free at lightfield.app
35:14 Every Tesla becomes a Starlink hotspot
43:53 What would be the ultimate SpaceX domain name?
45:47 Thanks to our partners at Rippling! Head to rippling.ai/twist and get the only AI built to give you full visibility across your startup and take complex actions across your entire business.
46:57 Is METR a fair watchdog for OpenAI?
54:50 Jason’s “Know Your Customer” plan for AI models
1:04:21 Meta’s deal to keep Zuckerberg in Cali
1:15:22 Why Jason would raise the minimum wage
1:19:29 Does Nathan Fielder give Liz Holmes a pass?
1:31:46 “A Short Stay in Hell” and “The Eureka Machine”
🎥 Watch the full episode here 👇
We are live folks!!
Come get ya Friday show with Jcal
OpenAI’s $1.25T Raise, SpaceX vs Verizon & AI Beats Doctors xitter.cf/i/broadcasts/1dGYlaEYO…
This Week in Startups retweeted
OpenAI’s $1.25T Raise, SpaceX vs Verizon & AI Beats Doctors xitter.cf/i/broadcasts/1dGYlaEYO…
This Week in Startups retweeted
Fantastic founder, amazing outcome for @Meowtel 🐈
You want your cat sitter to be accommodating, but Meowtel has spent 11 years saying no.
No dogs (“we’re Meowtel, not Wooftel”). No grooming. No Canadians. And no hawking products to cat owners.
Founder Sonia’s reasoning: U.S. cat sitting alone is a $6B market, and so far they’ve only reached 1% of it.
@Meowtel
Billy Kraft’s college startup ran for 18 months, had thousands of users, and made all of $17 from Google AdSense.
As CEO and co-founder of Path, Billy flipped the order: get customer commitments first, then build the product.
His first customer was Austin’s iconic Waterloo Records shop. Path’s team scanned CDs by hand, worked the register, and asked every store employee: “Where are you stuck?”
@billykraft, @pathsystems, @jason
They discovered Waterloo was running on MS-DOS, pen and paper, and computers that couldn’t talk to each other. Every end-of-day revenue report took several hours.
The experience informed Path’s pricing rule: charge based on the size of the pain. The first payment was a paper check, picked up in person.
Want more Tactical and Practical founder advice just like this, from veterans who know the game?
Get 100+ tips from our Founder Field Guide per year on our Substack. twistartups.substack.com
When answering a question from an investor, the longer you keep chattering away, the less credible you sound.
Answer with a yes, no, or a number. Then, stop. No more talking.
Brian once closed a presentation at a major pitch event by simply stating three numbers. He got a much bigger reaction than any rhetorical flourishes could have triggered.
@brgannon, @JoinLoop, @jason
When fundraising, Brian recommends expanding your vision.
Double the investors that you contact, and cut your raise time in half. His tactic: do one hour of outreach every morning, then give yourself a little treat, like a walk around the neighborhood.
Brian nearly failed his angel round by contacting only 7 investors. David Tisch told him he’d gotten lucky and pushed him to expand his list to 80.
Want more Tactical and Practical founder advice just like this, from veterans who know the game?
Get 100+ tips from our Founder Field Guide per year on our Substack. twistartups.substack.com
Kash (founder of TaxGPT) raised prices four times: $1,000 → $1,200 → $1,600 → $2,000 a year.
But this wasn’t mere trial and error. Kash was watching a specific metric: Trial-to-paid conversion. As long as it stayed above 60%, the market was absorbing the price hike. (Today it’s at 70–80% blended.)
And yes, existing customers were always grandfathered in.
@ChKashifAli, @AskTaxGPT, @jason
Kash’s biggest takeaway: Make sure you’re rolling out new features and price points deliberately, in stages, so that you can make sense of all the data later.
If a product launch lands alongside a price change, and conversion moves, you can’t know what caused it.
Want more Tactical and Practical founder advice just like this, from veterans who know the game?
Get 100+ tips from our Founder Field Guide per year on our Substack. twistartups.substack.com
One way to find out if you have product-market fit: build the test right into the product
When a Fastlane user hits a certain usage threshold, the app triggers the classic Sean Ellis survey question automatically:
“How would you feel if you could no longer use this?”
If 40%+ say “very disappointed,” CEO Jock Ferguson says that’s a strong PMF signal.
@jock_ferguson, @UseFastlane, @jason
To get there, the loop is straightforward: talk to users, build what they tell you they want, repeat.
Figure out exactly how people want to use your product, and then make it easy for them as possible. When people struggled to come up with their own ad prompts, Jock’s team redesigned onboarding to build users ready-made ads in 30 seconds.
Want more Tactical and Practical founder advice just like this, from veterans who know the game?
Get 100+ tips from our Founder Field Guide per year on our Substack. twistartups.substack.com
Kev from Streamfog rebuilt his entire app from scratch. But instead of starting a long internal QA cycle, he posted a message in his Discord asking for beta testers.
200 people joined in a day, sent logs, and gave him feedback. He says it’s one of the best launches he’s ever had.
@KevBondzio, @streamfog, @jason
Kev made joining Discord the last step of onboarding, so he sees every message, and he now has a full-time community manager. It works because the platform is already a vibrant community.
The payoff: feedback on new features within an hour.
One user asked for a Linux client near midnight, and 40 minutes later, he sent a screenshot of it running, built with Claude Code.
Want more Tactical and Practical founder advice just like this, from veterans who know the game?
Get 100+ tips from our Founder Field Guide per year on our Substack. twistartups.substack.com