Founding Moments

Nate Tingey

Founding Moments is a conversation series where founders and early employees break down the pivotal moments that shaped their journey and their companies. From the bets that paid off to the decisions that almost broke everything, each episode pulls out the lessons you can actually use.

Episodes

  1. Jun 24

    From Pain to Platform - Building Merge, with Shensi Ding

    Shensi Ding co-founded Merge after watching her own company lose deals it should have won — not on product, but on integrations. In this episode, she traces the path from teaching herself to code at 12 (building emo band fan sites in Boston) to building the unified API powering integrations for thousands of companies. She and Nate dig into why integrations went from "nice to have" to table stakes, why accounting was the hardest category Merge ever tackled, how founder-led sales carried them to $10M, and why she believes openness — not data silos — is the only durable moat in the AI era. A candid conversation about selling pain, building infrastructure customers can't afford to have break, and the pivotal decision to make AI adoption non-negotiable across the entire company. In this episode: (01:08) Learning to code at 12 — and why being "a loser" building band fan sites led to a CS degree at Columbia(02:14) Diverging paths after school: Gil to SF as a top engineer, Shensi to investment banking and growth investing(03:09) Chief of staff at Expanse (acquired by Palo Alto Networks) and a front-row seat to enterprise sales(04:05) The origin of Merge: losing deals purely on integrations, and why the market was about to get much worse(06:48) The first integrations — ticketing systems like Jira and ServiceNow(08:28) Why they launched with HRIS and ATS, and the TAM problem with starting in ATS alone(10:26) Accounting: the brutally hard third category (and why "hard to build" became a moat)(13:18) Why Merge has to hire genuinely sharp reps — and trains them across every category(14:05) Fundraising: $75M raised, and how the pitch shifted from "how is this different from Zapier?" to "can they expand beyond HR?"(15:19) Building ahead of the AI wave — knowledge bases, file storage, and being ready when the market arrived(17:05) Go-to-market evolution: founder-to-founder grinding to $10M, then a real SDR team and enterprise motion(18:29) Spotting early customers by "PMing" the prospect — and how Ramp became their first expense-management customer(19:54) Moving upmarket after Series B and why Merge segments enterprise by employee count, not customer count(22:35) Working through closed HRIS platforms and shifting the whole category toward openness(23:50) Open vs. closed in the AI era — and why siloed data is only a temporary moat(24:50) The consumer nuance: social platforms blocking bots vs. wearables like Whoop and Oura staying open(26:34) Why the categories never end — plus new bets on agentic tooling and LLM routing(27:31) How Merge's LLM routing works: smart fallbacks, white-labeling, and enforcing customer data contracts(29:26) The pivotal moment: making aggressive AI adoption mandatory across the entire company(30:33) The end goal — and who Merge is hiring across SF, NYC, and Berlin

    31 min
  2. May 9

    Build It. Sell It. Repeat. - A conversation with Clark Peterson

    Clark Peterson has been in the right place at the right time five times — and it was never an accident. From selling cell phones before most people had ever seen one, to building the nation's first nationwide cellular network, to pioneering cloud communications before anyone trusted the cloud, Clark has spent 35 years identifying windows of opportunity and moving fast before they close. In this conversation, Clark walks through the full arc: getting hired at Cellular One because he already owned a cell phone, sending a blank fax to Craig McCaw that launched three more companies, watching employees shop for houseboats as their stock hit a million dollars right before the dot-com bubble wiped it out, and convincing businesses to trust their phone systems to something called "the cloud." What comes through most is his instinct for timing — knowing when to build, when to go public, and when to sell. Key Moments [00:40] — How Clark paid his way through college with a mobile window tinting business, used one of the first cell phones to land a Yellow Pages ad, and got hired at Cellular One because he was the only candidate who'd actually used one. [03:10] — Why he turned down Pfizer after making more in his first two months at Cellular One than he would have made in an entire year at the pharmaceutical job he'd already accepted. [03:51] — The blank fax: Clark and colleagues sent Craig McCaw a completely blank page with only the words "what's next" — and the companies that followed: Nextlink, Nextel, and ClearWire. [05:02] — Why banks refused to fund Cellular One, projecting only 7% of the population would ever afford a cell phone, and how Michael Milken's junk bonds filled the gap. [07:44] — The houseboat lesson: why managing people when everyone's stock crosses a million dollars is harder than managing them in tough times — and what the dot-com bubble taught Clark about taking money off the table. [11:18] — How Carl Icahn skipped the boardroom, sat with a customer care rep for 30 minutes, and learned more about what was broken in the business than the entire C-suite in New York knew. [12:29] — Building ClearWire from scratch as Craig McCaw's first employee, proving the model in one market before raising money to scale, and going public three years later in a successful 2007 IPO. [21:25] — Selling Telesphere's $45M revenue business for $117M, then building Vonage's business division from zero to $800M — which Ericsson eventually acquired for $6.2 billion. [25:21] — Why being acquired by a company that already does what you do usually fails, and why the opposite is actually an opportunity to build something new with someone else's money. [36:26] — Ontologics: Clark's current venture using proprietary AI to analyze every patent filed worldwide, score portfolios, flag infringement, and predict where emerging technologies are heading. [42:10] — "It's so much harder to find an opportunity from the bench than if you're playing in the game." [57:19] — His dad's advice that's driven everything: "The harder you work, the luckier you get." About Clark Peterson Clark Peterson is a serial entrepreneur and telecom veteran who has built and exited companies across cellular, fiber, wireless data, and cloud communications. He co-founded the Cloud Communications Alliance, whose members today include Zoom and Cisco, and is currently building Ontologics, an AI-powered patent intelligence platform.

    59 min
  3. Apr 12

    Start a Company When Things Are Terrible - A conversation with David Leeds

    David Leeds spent nearly two decades building Tango Card from his basement in West Seattle — literally fulfilling gift card orders at midnight — into a company processing over $1.5 billion in rewards annually before being acquired by Blackhawk Network. But before Tango, he co-founded Fiber Tower, pitched 45 venture capital firms, got 45 rejections, and took it public anyway. What comes through in this conversation is his instinct for timing. He started Tango in January 2009, right in the teeth of the financial crisis, because he believed that was exactly the right moment. Then he threw out the existing playbook entirely — no delivery fees, no platform minimums, no reporting fees — in an industry where 15 to 30% fee stacks were completely normal. Microsoft was his first customer. Their finance team all closed their laptops when he explained the model. Show Notes Tango Card — acquired by Blackhawk Network (2023)Fiber Tower — telecom infrastructure, taken public via reverse merger (2007)Bing Rewards — Microsoft loyalty program, one of Tango's first integrationsgiftcertificates.com — Omaha-based competitor acquired by Tango post-fundraiseBlackhawk Network / Silver Lake — acquirer of Tango CardTimestamps [00:32] Growing up, studying abroad in Copenhagen, and choosing a program where English wasn't the native language [04:17] Nations Bank, Lexmark, and presenting to French leadership in broken French [06:38] Starting a consulting company in China — and why he hated being a consultant within a year [08:40] Stanford during the dot-com peak, graduating right as everything crashed [09:29] Founding Fiber Tower: four folding desks, no windows, 45 VC rejections [17:55] The core lesson: start a company when the economy is in ruins [20:10] January 2009 — launching Tango Card, self-funded, in the financial crisis [23:28] How a research note about gift card payment growth became a $1.5B business [35:52] The original product: a physical card, a website, and midnight basement fulfillment [39:30] Landing Microsoft as customer #1 and the moment their whole finance team closed their laptops [44:05] The business model that changed everything: zero fees, just spend your budget [54:38] Building a self-serve portal — and why his CTO tried to talk him out of it [1:06:29] How David recruited and kept great people through transparency and a mission everyone could actually recite [1:12:21] The Blackhawk acquisition — why global reach was the whole point [1:19:22] Why a gift card company keeps a sledgehammer in the office

    1h 22m
  4. Mar 20

    Your Software Is Worth Nothing — The Business Is Everything

    What happens when your startup fails — and why that might be the best thing that ever happens to you? Chris Chumley has spent his career building, breaking, and betting on software companies. From nearly getting expelled for sneaking into school to play Oregon Trail, to leading product at a venture-backed startup that cratered, to helping build CampusLogic from a handful of customers to a $50M ARR acquisition by Ellucian — Chris has seen every phase of the startup lifecycle up close. In this episode, Chris and Nate dig into the real lessons behind building great products: why your software is worth nothing (but your business is everything), how to stay differentiated when sales is screaming for me-too features, and why the best product strategy starts the moment you choose what to build. Chris also shares his framework for the "lighthouse" approach to roadmapping, what it really takes to build trust with a CEO, and why niching down — not boiling the ocean — is what took CampusLogic to $50M. Now a venture partner at Phoenix Ventures, Chris brings his operator lens to what he's seeing in early-stage investing today, including why pre-seed is getting harder, what he looks for in a founder, and why vibe coding both excites and scares him. Plus — a candid conversation about Claude Code, the future of engineering, and a question neither of them can fully answer: if AI does all the grunt work, how does the next generation actually learn?

    1h 15m

Ratings & Reviews

5
out of 5
3 Ratings

About

Founding Moments is a conversation series where founders and early employees break down the pivotal moments that shaped their journey and their companies. From the bets that paid off to the decisions that almost broke everything, each episode pulls out the lessons you can actually use.

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