Grant Lee is the Co-founder & CEO of Gamma, building instant PowerPoints, presentations, and websites with AI. As someone who’s made a lot of decks, its refreshing how Gamma thinks about slides starting with the words and narrative, using AI to build the design around the story. Gamma has put up impressive metrics, growing from zero to $50 million in ARR and 50 million users with only 30 employees. They’ve also had zero employee attrition, and a negative lifetime burn rate, with more cash in...
Jul 03, 2025•1 hr 31 min•Season 1Ep. 98
Ryan Sachtjen is the Co-founder and CEO of Threeflow, building software for employee benefits brokers and insurance carriers. We start with a deep dive into the nearly $2 trillion dollar employee benefits market, including the structural issues that actually give the smallest companies the most leverage. We also talk about insurance more broadly, AI opportunities in insurance, lessons from kickstarting a marketplace doing nearly $3B in volume, when his wife got cancer two months after closing Th...
Jun 26, 2025•1 hr 54 min•Season 1Ep. 98
Samir Kaji is the Co-founder and CEO of Allocate. This conversation is a deep dive into the private markets, the evolution of venture capital as an asset class, and how there are now 10x more private investment firms than public companies. We also unpack why 90% of venture funds simply can’t raise capital right now, advice for anyone raising a fund today, how to stand out as an emerging manager, why secondaries have become a primary driver of liquidity in venture, and how to navigate SPVs as a G...
Jun 19, 2025•1 hr 42 min•Season 1Ep. 97
Anamitra Banerji is the Co-founder of Afore Capital, an SF-based VC firm that specializes in investing in pre-seed stage companies. Our conversation gets into the evolution of Pre-Seed as a category, why Pre-Seed is more than option checks, what Afore looks for when backing founders before they even have a product, how to skip your Seed and go straight to a Series A, and how to run a fundraise process. We also get into Afore’s Founder in Residence program, why every VC started an accelerator, ho...
Jun 12, 2025•1 hr 36 min•Season 1Ep. 96
Eric Vishria is a General Partner at Benchmark Capital. Our conversation goes inside the new class of startups going zero to $100 million ARR in 12 months, the ways AI is changing company building, and how Eric and Benchmark make new investments. We get into the risk rewards of Series As today, how Benchmark competes to work with founders, and and why the best storytellers win. We also talk about parallels between the 90’s, 2000’s, and today, and how the archetype of successful founders has chan...
Jun 05, 2025•1 hr 46 min•Season 1Ep. 95
Sanjit Biswas is the Co-founder and CEO of Samsara, the fleet management and safety platform. At the time of publication, Samsara is a public company worth over $26 billion, and we unpack how exactly they went from zero to run rating at over $1.5 billion in revenue in ten years. We get into using AI to impact the physical world, how Samsara uses AI internally, and how their products prevent over 200,000 deaths per year. Sanjit has built two unicorns, and he shares everything he’s learned along t...
May 29, 2025•1 hr 32 min•Season 1Ep. 94
Michael Kim is the Founder of Cendana Capital, a fund of funds that makes anchor investments in very early stage VC funds. We talk characteristics of the best investors, how Cendana does diligence on fund managers, portfolio construction best practices, Michael’s “60x rule”, and why high ownership to fund size is the main driver of returns. We also get in to how VCs are using AI, the competition between Seed and multi-stage investors, why US endowments are under siege, and how secondaries are dr...
May 22, 2025•1 hr 55 min•Season 1Ep. 93
Mike Vichich is the Co-founder and CEO of Pursuit, which helps companies generate more revenue from the public sector. We talk about how AI is changing Helmer’s 7 Powers, how it’s impacting the government, if DOGE is actually working, building a startup in the Midwest, and how to disagree with your team. We also get into Mike’s prior company Wisely, and how they went from $11 in the bank account and unable to pay payroll for six months, to over $10 million ARR and a $187 million exit to Olo, a p...
May 15, 2025•1 hr 47 min•Season 1Ep. 92
Sam Ross is the Co-founder and CEO of Numeral. This conversation is a master class on all things growth at the zero to one stage. We talk early growth lessons from Airbnb, and stories from being one of the largest, earliest Facebook advertisers. We get into working backwards from pockets of strong demand to find business ideas, how to establish early social proof around your product, why you shouldn’t hire a growth person as your first growth hire, how he raised Numeral’s Series A in four days, ...
May 08, 2025•2 hr 1 min•Season 1Ep. 91
Spenser Skates is the Co-founder and CEO of Amplitude. Our conversation gets into the importance of data in product design and company building, how Amplitude is thinking about AI, and the future of user responsive software. We also get into the early days of building Amplitude, when to go multi-product, how to construct your board as a startup, hiring executives at various company stages, lessons from closing three acquisitions, lessons scaling to $300 million in ARR, inside Amplitude’s 2021 IP...
May 01, 2025•1 hr 44 min•Season 1Ep. 90
Dan Lorenc is the Co-founder and CEO of Chainguard, the safe source for open source. The internet runs on free, open source software. But as its risen in popularity, its become the latest attack point targeted by hackers and nation states. This conversation with Dan gets into the history of open source software, cloud computing, Linux, the software supply chain, how AI will impact it, and what the next big cyber attack will look like. Dan is an engineer, but he also loves sales and go-to-market....
Apr 24, 2025•1 hr 15 min
Colin Sidoti is the Co-founder and CEO of Clerk, the best way to build authentication and user management. I loved this conversation, because Colin is currently in the arena building Clerk. It has not been easy, and he takes us inside some of the harder moments of the past six years. We hit on three main themes: authentication; lessons raising multiple hard Seed extensions in the early days, including a recap before the A, and the demo that got a16z to invest; and things AI and MCP. We also talk...
Apr 17, 2025•1 hr 40 min•Season 1Ep. 88
Filip Kaliszan is the Founder & CEO of Verkada, the physical security company. Verkada started in 2016 by building the best camera for physical security teams, and has since evolved into a full suite of security products for buildings. Filip takes us inside Verkada’s rapid growth to almost a billion in annual revenue, over 2,000 employees, and raising capital from investors like Sequoia, Meritech, First Round, General Catalyst, and Next47. We get into how AI and LLMs are changing hardware, t...
Apr 10, 2025•1 hr 43 min•Season 1Ep. 87
Ofek Lavian is the Co-founder and CEO of Forage, the mission driven payments company. This is a special episode, because I’m an investor in Forage, and Ofek shares everything he’s learned building the company. We go deep on food stamps, also known as EBT or SNAP, the government program that provides over $200 billion dollars per year in benefits that help 42 million low income Americans buy food. Our conversation gets into lessons from Ofek’s time leading payments teams at Uber and Instacart, bu...
Apr 03, 2025•1 hr 13 min•Season 1Ep. 86
Ed Lando is the Co-founder of Pareto, where he’s been an early investor in over 25 unicorns, started and incubated over 10 companies, and was recently named the most active angel investor in the world according to Crunchbase. We get into how Ed first got started angel investing, how he built up deal flow, why he’s historically kept a low profile, and why he hasn’t raised outside capital. We also talk concentration vs diversification, why there’s many ways to build successful companies, advice on...
Mar 20, 2025•1 hr 45 min•Season 1Ep. 85
Tommy Nicholas is the Co-founder and CEO of Alloy, the identity and fraud prevention platform trusted by over 700 financial service companies. Our conversation explores the early days of fintech, why more consumer financial protections actually lead to more fraud, and gets into the weeds of various tactics he’s learned building a technical platform company like Alloy. We talk about embracing that the hard parts of company building are actually the best parts, why you’re most likely to give up wh...
Mar 14, 2025•1 hr 30 min•Season 1Ep. 84
Mike Murchison is the Co-founder and CEO of Ada, the AI-powered customer service automation platform. Ada’s product and scale puts Mike at the forefront at how AI is changing software and labor markets, and this conversation felt like both a glimpse into the future, and a look into the past, at a story of pure grit and determination, working seven customer service jobs at once. We talk about why management capabilities becomes even more important in AI-native companies, how customer service is c...
Mar 06, 2025•1 hr 33 min
Cam Doody is the Co-founder and General Partner of Brickyard, the venture capital firm moving founders to Chattanooga, Tennessee to lock-in with no distractions until they find product market fit. Brickyard is one of the most unique venture firms you’ll ever come across, and we get into how it how it was inspired by a 16x fund based in Chattanooga, why Cam and his co-founders started it during ZIRP, and why they hope everyone copies their model. We also get into Cam’s startup Bellhops, which he ...
Feb 27, 2025•1 hr 46 min
Eric Simons is the Co-founder and CEO of StackBlitz, best known for its breakout product Bolt, letting anyone build full stack apps from text, in the browser. Bolt launched in October of 2024, quickly growing from zero to a $20 million revenue run rate in two months, making it one of the fastest growing products ever. But Eric will be the first to tell you it wasn’t an overnight success - the product didn’t even work the first time they tried building it. We go behind the scenes of the seven yea...
Feb 20, 2025•1 hr 53 min•Season 1Ep. 81
Rick Zullo is the Founder of Equal Ventures. Our conversation gets into Equal’s unique approach to venture capital, thinking more like public market and private equity investors, and why they also think traction is overrated at Seed. We talk through Equal’s thesis-driven model, employing a team of product owners, only investing in only 3 to 5 themes at once, and Rick’s admiration of Charlie Munger. We also talk AI - who will benefit the most, what he does and doesn’t like in terms of investing i...
Feb 13, 2025•1 hr 40 min•Season 1Ep. 80
Villi Iltchev is the founder of Category Ventures, where he invests early in enterprise software startups. And he’s done it longer than almost anyone, building Salesforce’s corporate venture arm and investing early in companies like Airtable, Zapier, GitLab, Remote, Hubspot, Gusto, and Box. Fresh off raising his $160m Fund 1, we get into the opportunity he saw to start Category, and how San Francisco and Silicon Valley have changed over the past 30 years. He also shares his story growing up as a...
Feb 06, 2025•1 hr 49 min•Season 1Ep. 79
Rahul Sidhu is the co-founder of SPIDRTech and Aerodome, two companies in the public safety space. He’s sold both of them, and our conversation unpacks all the lessons he learned, what he did differently with his second company Aerodome, and why he sold only 17 months after starting it. If you tuned into last week’s episode, Paul told us to never talk to the cops. Rahul gives us the other side of the story, sharing his playbook for selling to police, the government, how he met Nikita Bier in hig...
Jan 30, 2025•1 hr 29 min
Paul Klein is the Founder and CEO of Browserbase, building infrastructure for AI browsers. Our conversation gets into the future of software and AI agents, why authentication is a huge problem in AI, how the best infrastructure companies become product companies, and the memo he wrote that convinced him to start Browserbase despite not wanting to build another company. A year ago, Paul was a relatively unknown commodity, and definitely did not want to raise venture capital again. He shares the p...
Jan 23, 2025•1 hr 53 min
You’re probably familiar with Baiju Bhatt’s work as the co-founder of Robinhood. But he’s also obsessed with space, and recently started Aetherflux, a space solar power company. We get into the physics of using lasers to beam solar power to the Earth, Aetherflux’s early roadmap, and how he went from zero to one going from building software to physical products. We also talk through the early days of Robinhood, getting turned down by hundreds of early investors, the accidental launch, how to know...
Jan 16, 2025•1 hr 18 min•Ep. 76
Sheel Mohnot is the Co-founder of Better Tomorrow Ventures, an early stage fintech focused fund leading rounds in pre-seed and seed-stage companies. Our conversation weaves through Sheel’s two decades of building and investing in fintech, starting BTV, and why they started a fintech-focused accelerator, The Mint. Fun facts on Sheel, he was a contestant on the Zoom Bachelor during COVID lockdowns, in a Justin Bieber music video, got married in the Taco Bell Metaverse, and was once banned from Ube...
Jan 09, 2025•1 hr 32 min•Ep. 75
Chris Hulls is the co-founder and CEO of Life360, the social network for families. At the time of recording, its the 15th largest app in the US, with over $330 million in annual revenue, and valued at over $3 billion in the public markets. We go inside the two decade journey building Life360, competing against Sam Altman and Woz, almost getting cancelled on TikTok, and going public twice - first in Australia, then again in the US. Timestamps: (00:00) Intro (02:04) Why CEO’s are getting more auth...
Jan 02, 2025•1 hr 21 min
Joseph Nelson is the Co-founder and CEO of Roboflow, making the world programmable by building computer vision tools for developers and enterprises. We talk about how computer vision creates a new paradigm to program the world, and how visual AI is the missing piece of AGI. Joseph also shares multiple live product examples, how computer vision unlocks new data sources, lessons from Stripe and Palantir, building business models in developer tools, his experience working with David Sacks, and deve...
Dec 19, 2024•1 hr 58 min
Austin Rief is the Co-founder & CEO of Morning Brew, building the Wall Street Journal for the next generation. They started the company in 2017, and grew it to 6 million subscribers and $70 million in revenue in six years. We talk through the journey starting Morning Brew with Co-founder Alex Lieberman while students at the University of Michigan, and Austin's playbook for starting a new media company from scratch today. We get into the creator economy, early stage investing, ad based busine...
Dec 12, 2024•1 hr 13 min
Niels Hoven is the founder of Mentava, building software to accelerate kids’ education, starting with teaching two year old’s to read. We talk about how public education isn’t designed for ambitious kids, the power of hater marketing, product design from zero to one, how too much data leads to Frankenstein products, Seed stage fundraising advice, parenting hacks, why AI won’t have a big impact on education, and the future of elite higher ed. For full show notes, visit: https://highlightai.com/sh...
Dec 05, 2024•1 hr 46 min
Nirav Tolia is the co-founder and two-time CEO of Nextdoor. He started the company in 2011, stepped down as CEO in 2018, watched the company go public in 2021, and re-joined as CEO the summer of 2024. He also founded Epinions which IPO’d in 2004, and before that was an early employee at Yahoo. We go inside the decision to re-join the company after he thought he’d never come back, and how Nextdoor’s trying to act like a startup while running a public company. He also takes us back to the very ear...
Nov 21, 2024•1 hr 20 min
