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Get a behind the scenes look into the founding stories of your favorite companies. Learn how the industries they operate in actually work, and learn playbooks and tactics you can use to launch and scale your own business.
Copyright: © Turner Novak
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 public company.
Thanks to Jack Altman and Blake Robbins for their help brainstorming topics for Mike!
Timestamps:
(3:21) How AI changes Helmer’s 7 Powers
(17:06) What becomes important in AI-first economy
(21:02) How AI interfaces with the government
(24:02) “The rules intended to save taxpayer money ironically cause taxpayer money to be wasted”
(29:34) How change orders impact public sector costs
(33:20) Why DOGE has not impacted US government spending yet
(38:15) Three pieces of wisdom from 2nd-time founders
(41:44) Starting Pursuit to make selling to the public sector as easy as the private sector
(45:35) Why cities grow expenses 5x faster than tax revenue
(51:42) Pros + Cons of building startups in Ann Arbor, MI
(57:43) Hiring talent density in the Midwest
(59:30) Starting his first company to fix consumer credit cards
(1:08:50) Pivoting Wisely to restaurant loyalty
(1:12:49) $11 in the bank, missing payroll for six months
(1:15:21) Embarrassing demo at an Ann Arbor tech meetup
(1:18:18) Why CEOs don’t always have to be right
(1:20:54) How to disagree
(1:25:48) Hiring at Pursuit
(1:28:30) “A bad day with customers is better than the best day in the office”
(1:31:33) Crashing their first customer’s PoS on Labor Day Weekend
(1:35:55) Using “The Cadence” to hit $10M ARR
(1:41:55) Selling Wisely to Olo for $187M
Referenced
Follow Mike
Twitter: https://x.com/mikevichich
LinkedIn: https://www.linkedin.com/in/mikevichich
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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, and why sales tax is so complicated and how they’re using AI to make it easy.
Timestamps:
(3:03) Why sales tax is so complicated
(8:06) Running crazy Facebook ads in 2013
(11:58) Why you need to be aggressive on new growth channels
(16:55) How strong retention unlocks massive businesses
(18:24) Using pockets of demand to find business ideas
(21:34) Balancing performance vs brand marketing
(25:45) How to build a brand from scratch
(29:11) When cold outbound actually works
(36:18) Building early social proof around your product
(43:33) Don’t hire career growth people for growth roles
(49:31) Lessons building a jewelry business doing $30m in revenue
(58:44) How the 2018 Wayfair v South Dakota decision led to Numeral
(1:05:04) Hacking an early product together with spreadsheets
(1:07:32) Automating the product
(1:15:26) What happens if you don’t pay sales tax
(1:20:41) How Numeral uses AI and LLMs internally
(1:26:41) How to compete against non-technical incumbents
(1:32:57) Why they raised VC for Numeral
(1:38:19) Raising a Series A in four days
(1:45:43) How big can a sales tax company really be?
(1:48:55) Creating a better global tax system
(1:54:31) How San Francisco is losing its soul
Referenced
Check out Numeral: https://www.numeralhq.com/
South Dakota v Wayfair: https://en.wikipedia.org/wiki/South_Dakota_v._Wayfair,_Inc.
Follow Sam
Twitter: https://x.com/SpamRoss
LinkedIn: https://www.linkedin.com/in/sambross/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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 IPO, and what most people get wrong about Founder Mode.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:45) Using data to build great products
(8:31) Why data is existential to every business
(13:14) How to go multi-product
(15:48) Every startup becomes a distribution company
(19:29) Lessons from three acquisitions
(29:09) AI hasn’t changed B2B SaaS yet
(31:24) Challenges of incorporating AI in B2B SaaS
(33:09) Amplitude’s AI experiments
(36:29) Navigating technology hype cycles as a public company
(39:40) Amplitude’s opportunity in LLMs
(43:08) User responsive software
(46:16) Surprising things that slow your speed of execution
(51:27) What people get wrong about Founder Mode
(59:48) Pivoting into Amplitude after YC
(1:04:42) Nine months to raise Amplitude’s first round
(1:08:31) Surprises from closing the first customers
(1:12:46) Two sales lessons for technical founders
(1:13:44) Scaling to $300M+ ARR
(1:17:14) How to choose board members
(1:19:55) Inside Amplitude’s IPO
(1:21:56) “Stock price is an output of the business”
(1:26:36) Evolving from startup founder to public company CEO
(1:31:54) How hiring execs changes as you scale
(1:34:32) Why DEI is important at Amplitude
(1:39:46) Relevance of gaming and startups
Referenced
Try Amplitude: https://amplitude.com/
Careers at Amplitude: https://amplitude.com/careers
Moxie Marlinspike’s web3 article:https://moxie.org/2022/01/07/web3-first-impressions.html
Sheep Logic: https://www.epsilontheory.com/sheep-logic/
Follow Spenser
Twitter: https://x.com/spenserskates
LinkedIn: https://www.linkedin.com/in/spenserskates
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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. We unpack how Chainguard went from zero to 150 customers and a $40m ARR in two years.
Chainguard just announced a $350 million Series D led by Kleiner and IVP, and Dan unpacks the round, plus shares his secret methodology for valuing the company.
A big thank you to Dan’s Co-founder Kim Lewandowski, to Clay Fisher @ Spark, Bogomil Balkansky & Andrew Reed @ Sequoia, and Tom Loverro @ IVP for their help brainstorming topics for Dan.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(3:26) A safe source for open source
(4:57) The software supply chain
(7:19) Can you trust open source code with contributors in Russia?
(9:43) Malware attack that almost took down the entire internet
(12:40) What the next big cyber attack will look like
(15:12) How will AI impact the software supply chain
(17:53) The history of cloud computing
(21:42) Why all cloud computing runs on Linux
(23:16) How Linux + Linux distros work
(29:28) Automating open source security
(32:43) Chainguard roadmap: Libraries and VMs
(36:40) Focusing on FedRAMP
(42:44) Impact of DOGE
(44:06) Zero to $40m ARR in two years
(45:40) Learning to love sales as a technical founder
(47:24) Lessons from Frank Slootman
(51:15) How to create urgency in sales
(53:16) How to build a sales team
(58:23) Hiring Ryan Carlson from Wiz & Okta
(1:01:45) Inside Chainguard’s $350m Series D
(1:07:41) Vibe coding + Dan’s software stack
(1:09:51) Cutting his hair in front of the entire company
(1:10:27) Wearing a different suit to each board meeting
(1:12:32) Bogomil, world’s best SDR
Referenced
Check out Chainguard: https://www.chainguard.dev/
Jobs at Chainguard: https://www.chainguard.dev/careers
Prior episode with Dan: https://www.youtube.com/watch?v=AC4cOJ9n_Z8
Linux Origin Email: https://www.reddit.com/r/linux/comments/mmmlh3/linux_has_a_interested_history_this_is_one_of/
The Qualified Sales Leader: https://www.amazon.com/Qualified-Sales-Leader-Proven-Lessons/dp/0578895064
Julius, AI data analysis: https://julius.ai/
Claude Code: https://www.anthropic.com/claude-code
World’s best SDR: https://x.com/BogieBalkansky/status/1913269714882814350
2025 Chainguard Assemble Keynote: https://www.youtube.com/watch?v=adfU9LJg3I0
Follow Dan
Twitter: https://x.com/lorenc_dan
LinkedIn: https://www.linkedin.com/in/danlorenc/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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 founding a company with his brother, building a compound startup, why components are the new APIs, and what he learned about audacious goals from John Collison @ Stripe
A big thank you to Reid Christian @ CRV, Paul Klein @ Browserbase, and Joseph Nelson @ Roboflow for helping brainstorm topics for Colin.
Timestamps:
(3:39) The best developer tool for authentication and user management
(5:45) The easiest way to set up billing
(7:13) Building a compound startup
(9:15) Lesson on audacious goals from John Collison
(12:40) Developer tools are now trusted category experts
(13:47) How auth impacts billing, CRM, marketing, analytics
(19:44) Why auth is always changing
(25:40) Coming up with the idea for Clerk
(29:24) What its like starting a company with your brother
(30:58) Living in a basement during Clerks early days
(35:33) Getting early users narrowing focus in South Park Commons
(40:10) Fundraising lessons from struggling to raise
(43:46) The trick that raised Clerk’s first round from S28
(45:09) Launching + the first Seed extension
(50:15) Sequoia’s feedback that improved conversion rates
(52:22) Why a16z led Clerk’s 2nd Seed extension
(58:11) How to do a recap before Series A
(1:03:34) Changing Clerk’s pitch to scare investors
(1:08:56) Fundraising advice “Why partner alignment is all that matters”
(1:11:42) Fast Series A and breaking 7%/week growth
(1:16:32) Negotiating Clerk’s Series B at the bar
(1:22:15) Investors in the arena vs in their mansions
(1:27:57) The three ways AI is changing authentication
(1:31:21) Why AI agents all try to steal free AI credits
(1:33:09) Remember to have fun
(1:36:24) Building a better product to compete in a crowded market
Referenced
Try Clerk: https://clerk.com/
Jobs at Clerk: https://clerk.com/careers
Martin Casado’s tweet https://x.com/martin_casado/status/1558134697753841664
Try Inngest: https://www.inngest.com/
Follow Colin
Twitter: https://x.com/tweetsbycolin
LinkedIn: https://www.linkedin.com/in/colin-sidoti-751a219
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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, the power of customer therapy, how Filip iterated on early startup ideas, inside Verkada’s very difficult first funding round, how signing their first big customers changed the trajectory of the business, and how to think about adding new products over time.
We also talk through Verkada’s commitment to in-person work in the summer of 2020, how you should evaluate joining a startup as an employee, Verkada’s “software zero” employee bonus policy, and building a rooftop bar for the office.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:20) Verkada, the physical security technology company + Demo!
(11:02) Building software powered hardware
(12:56) LLM opportunities in cameras
(15:49) Filip’s lifelong fascination with photography
(17:57) Taking one year to come up with the idea for Verkada
(22:27) Building his own home security system to learn the $16B market
(27:14) Why hardware experimentation is cheaper and easier than you’d think
(30:36) The importance of customer therapy
(32:37) How to get your first customers, importance of quick time to demo
(35:06) Why early fundraising was so hard
(40:38) Verkada’s first big customer
(42:23) How to decide what startup to join
(45:45) The opportunity in “smart building tech”
(50:34) How to launch new product lines
(58:07) Re-architecting the security industry to be software-native
(1:02:31) How hiring and managing a team changes as you scale
(1:08:55) Why each team at Verkada has its own recruiters
(1:14:00) Adding senior leaders to the team as you scale
(1:17:06) Evolving from introverted engineer to CEO of multi-thousand person company
(1:21:59) Verkada’s cool office and focus on in-person work during COVID
(1:28:12) Building a rooftop bar on the office
(1:32:20) Verkada’s Software Zero employee bonus program with 40x ROI
(1:36:00) How Filip thinks about IPO vs staying private
Referenced
Verkada: https://www.verkada.com/
Open roles at Verkada: https://www.verkada.com/careers/
Follow Filip
LinkedIn: https://www.linkedin.com/in/kaliszan/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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, building Instacart’s EBT program up to 40 employees and 10% of its total revenue, and why Ofek is so passionate about helping low income Americans.
We get into the history of food stamps, market dynamics that led to low online adoption, the days Ofek thought Forage might not make it all the way to now working with the biggest players in online grocery, like Uber and DoorDash, and the long-term opportunity Forage has to build the rails the government uses to distribute trillions of dollars of restricted consumer benefits.
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try it here: https://bit.ly/NumeralThePeel
Timestamps:
(4:53) Forage: Helping 42m Americans buy food
(5:24) History of food stamps & EBT
(9:26) Growing up as an immigrant family with low food access
(11:39) 90% of EBT recipients are elderly, disabled, or working parents
(12:39) How Forage sells revenue to its customers
(14:15) Building Instacart’s EBT program during COVID
(18:25) Why no one built an EBT payments product
(22:13) Joining Forage as a Co-founder
(25:01) Why government payments are so hard
(30:25) Growing 15x in six months
(33:52) Underdiscussed mental health challenges of startups
(37:06) How the political environment impacts EBT
(43:20) Why Forage charges more than competitors
(45:58) Seasonality in EBT spend
(46:59) Why early investors passed on Forage
(48:10) The trillion dollar opportunity in restricted payments
(50:56) “ There's no single idea that has destroyed more business value on planet Earth than the idea that micromanagement is bad.”
(54:45) Why Forage doesn’t care about job titles
(58:51) Lessons backpacking across 28 countries after college
(1:02:09) How to travel on a budget
(1:04:24) Importance of health
(1:06:15) Saving a friends life on Mount Everest
Referenced
Forage: https://www.joinforage.com/
Ofek’s viral tweet: https://x.com/OfekLavian/status/1766950034581700697
Follow Ofek
Twitter: https://x.com/OfekLavian
LinkedIn: https://www.linkedin.com/in/ofeklavian/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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 hiring your first employees, and his playbook for incubating companies at Pareto, which is where he focuses most of his time.
Timestamps:
(0:00) Intro
(2:51) Getting into angel investing
(3:58) Debating high vs low PR strategies
(8:27) How to start building deal flow when angel investing
(10:00) Pareto: first investor in people leaving school or their job
(12:05) Evolving from angel to fund
(14:57) Why Ed didn’t raise outside capital
(20:33) Concentration vs diversification
(28:29) Investing in non-sexy categories
(32:50) There’s no one right way to build a company
(36:03) When to go against traditional wisdom
(39:36) Lessons from his anti-portfolio
(45:59) Ed’s close relationship with his parents(
(49:04) How we’re using AI
(54:04) Incubating companies
(58:38) Investing beyond spreadsheets and DCF models
(1:05:49) How to trust your intuition investing
(1:09:47) How to move fast
(1:14:24) What most people get wrong when incubating companies
(1:18:40) How to hire your first employees
(1:26:27) Navigating hype when building and investing
1:29:59 Venture math and the Power Law
1:35:33 How Ed and Pareto’s strategy might break
1:38:45 Differences between the US and Europe
Referenced
Pareto: https://pareto20.com/
Misfit Market: https://www.misfitsmarket.com/
Catalina Crunch: https://catalinacrunch.com/
Zamp: https://zamp.com/
Magnus Carlsen on Joe Rogan: https://www.youtube.com/watch?v=ybuJ_nIXwGE
Follow Ed
Twitter: https://x.com/edwardlando
LinkedIn: https://www.linkedin.com/in/edwardlando/
Substack: https://edwardlando.substack.com/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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 when things first start getting better, using hands-on sales implementations in the early days to gave Alloy product market fit on steroids, how hiring changes as you scale, getting 100’s of no’s over 20 months raising their Seed round, and why TAM doesn’t matter.
Thanks to Charley Ma for his help brainstorming topics for Tommy!
Thanks to Numeral for supporting this episode, the end-to-end platform for sales tax and compliance. Try them here: https://bit.ly/NumeralThePeel
Timestamps:
(3:56) The platform to manage fraud
(5:48) What fintech risk was like in the early 2010’s
(14:34) Why company building never gets easier
(19:30) Reasons the hard stuff is actually the good stuff
(24:00) You’re most likely to give up when things start getting better
(33:47) Doing hands-on sales implementation to get PMF on steroids
(42:26) Deciding when PLG or hands-on sales will work best
(52:33) Why more consumer financial protections leads to more fraud
(58:14) 20 months to raise $2m vs $200m from a spreadsheet
(1:06:32) “Make yourself look like a good investment”
(1:10:14) Why TAM doesn’t matter
(1:14:35) How to hire collaborative problem solvers
(1:24:38) Why Alloy didn’t do much marketing early on
Referenced
Try Alloy: https://www.alloy.com/
Charley Ma’s Pod Episode: https://youtu.be/5cxgB1_q2lw
Try Artie: https://www.artie.com/
Follow Tommy
Twitter: https://x.com/tommyrva
LinkedIn: https://www.linkedin.com/in/tommynicholas
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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 changing from a cost center to a revenue driver, and how to talk to customers more as you scale.
We also get into why AI is still underhyped, what truly AI native software looks like, the realities of selling enterprise AI software today, and advice for anyone building an AI agent from scratch.
Thanks to Boris Wertz and Fahd Ananta for their help brainstorming topics for Mike!
Timestamps:
(00:00) Intro
(03:49) Making customer service extraordinary for everyone
(05:44) Management becomes more important in AI-first companies
(12:13) From customer inquiry to solution in production, fully autonomously
(16:01) Why companies talk to customers less as they grow
(20:36) Creating new products from customer service data
(22:45) Broken incentives in customer service
(26:10) Working 7 customer service agent jobs at once for a year
(37:19) Why pivoting to Ada felt like failure
(46:11) How Mike would build an AI agent from scratch today
(49:15) Ways AI will change how we build and manage companies
(56:44) Why the best managers are great users of AI
(1:00:27) How the top 1% of people are using LLMs
(1:06:22) Realities of selling enterprise AI software today
(1:11:02) Building a sales team from scratch
(1:15:21) Reflecting on Ada’s scale + doubling the last six months
(1:16:41) Biggest software category of all-time ($750B)
(1:19:51) Why AI is still under hyped
(1:21:01) Ego is the biggest inhibitor to AI adoption
(1:23:33) How AI will fuel explosion of creativity and productivity
(1:25:20) Large companies will benefit the most from AI
(1:27:41) Multi-modal language models and autonomous (computers
Referenced
Try Ada: https://www.ada.cx/
Follow Mike
Twitter: https://twitter.com/mimurchison
LinkedIn: https://www.linkedin.com/in/mikemurchison
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
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