Founders in Arms

• Embrace the Suck: How Olo Survived 10 Years to Product-Market Fit With Noah Glass

  Noah Glass is the founder and CEO of Olo, an enterprise platform for mobile and online ordering that powers digital commerce for 800+ restaurant brands and nearly 90,000 locations. Founded in 2005, Olo went public in 2021 at a $3.5B valuation and was acquired by Thoma Bravo in 2024—a 20-year journey from scrappy startup to category leader.What you'll learn:Why Olo's first 10 years required extreme "pain tolerance" waiting for product-market fitThe B2C to B2B pivot that transformed their unit economics from burning $15 per customer to earning revenue while scalingHow "embrace the suck"—borrowed from the Marine Corps—became the cultural mantra that kept the team goingWhy going public was about customer confidence and long-term credibility, not exit or liquidityThe role of industry advisors in bridging credibility gaps when selling to traditional enterprisesHow adding delivery-as-a-service (Dispatch) in 2015 unlocked escape velocity and scale advantageThe challenges and benefits of operating as a public company in a misunderstood industryWhy partnering with Thoma Bravo PE offers better alignment than quarterly public market pressuresNoah's philosophy on founder loyalty and the lifelong bonds formed with early team membersWhy the current "homegrown tech stack" trend in enterprise is a passing fad that misses SaaS fundamentalsIn this episode, we cover:(00:00) Introduction and the "embrace the suck" mentality(01:03) Early days and the long wait for product-market fit(05:30) Why YC's "grow fast or quit" advice doesn't apply to every company(08:06) The deep bonds formed with early team members(12:14) Deciding between B2B vs B2C business models(13:34) The B2C beginning and Good Morning America moment(16:08) The pivot to B2B enterprise software(20:43) How third-party delivery and DoorDash changed the industry(23:04) The journey as a public company (2021-2024)(27:49) Why going public signaled long-term stability to enterprise customers(30:15) Operating under private equity with Thoma Bravo(36:10) Breaking into enterprise sales with industry advisors(44:45) The importance of reliability at scale for enterprise(46:58) Thinking about market size and expansion in vertical software(48:25) Rapid fire: Which founder inspires you most(49:01) Uncomfortable feedback on being overly loyal(50:48) Current trend prediction: Homegrown enterprise software is a fad

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• Building Infrastructure for the Agentic Web with Parag Agrawal

  Parag Agrawal is the co-founder and CEO of Parallel, building infrastructure for the agentic web. Previously CEO of Twitter, Parag now leads a company architecting how AI agents will interact with the open web at orders of magnitude beyond current human scale. Two years after founding in stealth mode, Parallel recently announced a $100M Series B co-led by Kleiner Perkins and Index Ventures.What you'll learn:Why everything built for human web consumption will become irrelevant when agents become the primary usersHow Parallel's APIs enable agents to search, fetch, and monitor the web with unprecedented scale and speedThe evolution from simple tool calls to autonomous sub-agents with real decision-making capabilityWhy the web must transition from "pull" (searching on demand) to "push" (alerting when conditions are met)The new business models needed to compensate content creators in an agent-driven webParag's counterintuitive approach to fundraising: why VC rejections don't sting but customer rejections doThe rational game VCs play that founders misinterpret as genuine enthusiasmWhy Parag believes we're not in an AI bubble—but an overreaction is coming (and it'll be faster than dot-com)How Parallel built quietly for a year before product-market fit arrived with the agent explosionThe operational philosophy of extreme in-person collaboration that shaped Parallel's early cultureIn this episode, we cover:(00:00) Introduction and Parallel's mission(01:02) What Parallel's APIs enable for AI agents(02:43) Practical examples: coding agents, sales automation, research(04:57) The conviction bet on agents before the market existed(10:54) New business models for content in the agentic web(20:22) The $100M Series B fundraise and going public(23:03) Why Parallel built in stealth with carefully chosen early customers(24:55) Current scale and product offerings(30:42) The evolution from tools to sub-agents to push-based web(33:13) Are we in an AI bubble? Parag's nuanced perspective(36:34) The mental models behind fundraising vs customer rejections(38:37) Why VC enthusiasm is rational strategy, not signal(45:37) Biggest career mistake: delaying Twitter's algorithmic timeline(48:28) The compounding cost of six-month delays(50:09) Finding inspiration in "re-founders" like Satya Nadella(51:54) The most rewarding part: watching customers do unexpected things(52:43) In-person culture and the transition to remote-friendly

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• Sphere's $21M Series A: Nicholas Rudder on Building Cross-Border Compliance

  Nicholas Rudder is the co-founder and CEO of Sphere, an AI-powered cross-border tax compliance platform that helps businesses navigate international sales tax, VAT, and GST regulations. After pivoting from a failed EdTech marketplace and losing his technical co-founder, Nicholas just raised $21M in Series A funding from Andreessen Horowitz—a remarkable comeback story that includes selling his first five contracts using only a Figma prototype.What you'll learn:How Sphere is becoming the "Deel of revenue compliance" for global businessesWhy Nicholas pivoted from EdTech after 18 months and what made him choose tax complianceThe strategy of selling contracts with a high-fidelity Figma prototype before building the productHow to convince investors to back a pivot when your co-founder has leftWhy businesses struggle with international tax compliance and how AI solves itThe importance of hiring an internal recruiter once you raise significant fundingWhy San Francisco remains the best place to build a startup despite the challengesHow YC's network helped navigate a critical health insurance crisisThe advantage of being a solo founder when recruiting high-quality founding engineersWhy raising from a position of strength creates better fundraising dynamicsIn this episode, we cover:(00:00) Introduction to Nicholas Rudder and Sphere(01:10) The EdTech marketplace that didn't work(03:08) Why EdTech is such a difficult market(09:16) The hard pivot to tax compliance(10:56) Selling five contracts with a Figma prototype(13:10) When the co-founder left and twins arrived early(21:58) Why international tax compliance is broken(27:10) Sphere's vision as the "Deel of revenue compliance"(31:34) The unintentional path to Andreessen Horowitz(38:54) Why VCs all know when you're raising(41:37) Building Sphere in SF vs. the UK or Australia(46:23) Immad's advice on hiring internal recruiters(51:14) Rapid fire: Founder inspirations and lessons learned

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• Building a LinkedIn for Hourly Workers with Instawork's Sumir Meghani

  Sumir Meghani is the founder and CEO of Instawork, a staffing marketplace connecting 9 million hourly workers with businesses that need flexible labor. Starting with just line cooks in San Francisco restaurants, Instawork now serves warehouses, stadiums, hotels, and hospitality businesses across the country, creating what Sumir calls "employment at the touch of a button."What you'll learn:Why starting "boring and narrow" (one city, one job type) is the key to marketplace successHow Instawork is building a "LinkedIn for hourly workers" with hundreds of data points per profileThe hidden costs of 100%+ annual turnover in restaurants and hospitalityWhy people actually want to work MORE hours when friction is removedThe concept of "robot wranglers" as the next major labor categoryHow Instawork is using its worker pool to train physical AI and robotics modelsThe difference between "leading by disappointment" vs. celebrating wins as a CEOWhy labor costs range from 30% (restaurants) to 80% (hospitals) of revenueThe labor market as a "Tetris board" of micro-jobs and available workersWhy Silicon Valley undervalues hourly work despite 100 million workers depending on itIn this episode, we cover:(00:00) Introduction and YPO CEO forum discussion(03:42) Sumir's journey from Groupon to founding InstaWork(04:58) The restaurant visit that sparked the idea(06:28) Why the hourly labor shortage is a global problem(08:07) Building profiles for 9 million workers(08:54) Starting narrow: San Francisco restaurants and line cooks only(12:28) The hourly worker crisis in hospitality(13:04) Why wages haven't risen despite labor shortages(15:58) The true cost of labor beyond hourly rates(17:48) AI's role in reducing onboarding friction(19:42) Physical AI and the future of robotics(20:16) Introducing "robot wranglers" as a new labor category(22:36) Using InstaWork's workforce to train robot models(23:34) Navigating the AI hype cycle as a consumer(26:47) White collar vs. blue collar labor market dynamics(29:29) Why more jobs will shift to physical industries(30:43) The cultural bias against hourly work in Silicon Valley(32:11) Rapid fire: Biggest entrepreneurial mistakes(33:36) Most rewarding parts of the founder journey(34:30) Why Silicon Valley should start simple, not big(36:30) The uncomfortable feedback: "Leading by disappointment"(38:50) Balancing high standards with celebration(39:58) What inspires Sumir: Physical AI and robotics innovation

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• David vs. Goliath in the Wearables Industry With Eric Migicovsky

  We're reposting this episode following major news: Pebble officially relaunched its companion app on iOS and Android, bringing exciting and new apps and watch faces to both new Pebble devices and original watches. The Pebble 2 Duo has begun shipping to customers who preordered earlier this year.Eric Migicovsky is the Founder of Core Devices, and the original founder of Pebble, the pioneering smartwatch that raised $10 million on Kickstarter before being acquired. Eric has launched Core Devices to continue building the smartwatch platform he believes in, complete with Google's newly open-sourced Pebble operating system.What you'll learn:1. The Kickstarter phenomenon: How Pebble became one of the first massive Kickstarter successes, raising $600K in the first day with a $100K goal2. Hardware's inventory trap: Why missing revenue projections by 20% ($80M vs $100M target) created a $20M inventory crisis that nearly sank Pebble3. The sustainable hardware model: Eric's new approach of targeting profitability at 5,000 units and eliminating inventory risk through pre-orders4. Inventor vs. founder mindset: The difference between building products you love versus building scalable companies5. Fighting Big Tech: How Eric's Beeper Mini challenged Apple's iMessage monopoly and led to DOJ antitrust action6. Getting software from Google: The surprising story of how Google open-sourced Pebble's operating system to enable Core Devices7. Hardware manufacturing today: Why building smartwatches is easier now than in 2011, and what's still challenging8. The artisanal hardware movement: Building premium, limited-run products for passionate niche audiences9. Regulatory battles: Apple's API restrictions and how they limit third-party smartwatch functionality10. AI integration: Adding ChatGPT and voice capabilities to modern smartwatchesIn this episode, we cover:(00:00) Introduction and reconnecting with Eric(01:18) The Core Devices relaunch and getting Pebble IP from Google(02:33) Eric and Raj's Waterloo connection and early entrepreneurship(04:48) From Pebble's precursor to YC and the smartwatch vision(09:30) The legendary Kickstarter launch day and calling Raj at 2am(14:00) Five years of overnight success and authentic marketing(16:07) Inventor vs. founder mindset and product obsession(19:21) The 2015 inventory crisis that changed everything(27:20) Eric's new sustainable hardware model with Core Devices(32:00) Using existing Pebble cases and Google's open-source software(36:58) The artisanal approach: 3 people, no VCs, limited production runs(41:14) AI integration and ChatGPT on the wrist(49:36) Secondary markets and public company trading restrictions

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