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Startup Growth Podcast
Fondo
25 episodes
4 days ago
Fondo is an all-in-one accounting platform for startups. Get your books closed, taxes filed, and cash back from the IRS.
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Fondo is an all-in-one accounting platform for startups. Get your books closed, taxes filed, and cash back from the IRS.
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Marketing
Business,
Entrepreneurship
Episodes (20/25)
Startup Growth Podcast
Daivik Goel | From Bootstrap to Batch, Last-Minute YC Submit & Why Fintech Speed Matters

Daivik Goel is Co-founder & CEO of Shor, a global payroll platform for startups. Traditional EOR providers charge around $7,000 per year to manage an employee earning $20,000 per year. Shor uses automation to reduce costs and embeds payroll actions into Slack and WhatsApp through AI agents, so founders can request tax documents or payment updates without opening another dashboard.

Daivik and co-founder Avi Konduru submitted their YC application at 7:59 PM, one minute before the deadline. After multiple prior rejections, they got an interview, then a follow-up call, then acceptance. They started YC with a crypto payment idea, pivoted five weeks before demo day to global payroll—a problem they'd worked on two years earlier—and shipped contractor payroll within a week. They've since raised funding and are scaling.

‍

Key Topics Covered:

• What Shor is: global payroll/EOR rebuilt for startups; automation handles ops, AI teammates deliver docs/actions in Slack/WhatsApp.

• From clever to sellable: pivoted inside YC from crypto/fiat rails to payroll where they had access and clear pain.

• Cost math that breaks: why legacy EORs charging ~$7k/yr on a $20k salary fail SMB/unit economics—and how Shor attacks the middle.

• Ship speed as strategy: prior fintech muscle let them launch contractor payroll in one week (KYC/KYB, payouts, tax flows).

• Design →  dashboards: move work to the user (chat interfaces), keep humans making decisions, let AI do the background jobs.

• Distribution as a moat: serve the massive long tail priced out by incumbents; win on affordability + responsiveness.

• YC pragmatism: plain-English interviews beat pitch theater; momentum over mockups.

• Execution after Demo Day: demand first, fundraising next, delivery always—scaling compliance/country coverage without losing speed.

• Founder operating cadence: daily inches over hype cycles; embrace “pivot hell,” but pick battles you can actually win with customers.

• Finance stack mindset: reliability and support matter most when back-office tools fail—opt for vendors who show up.

‍

Chapters

(00:00) Cold open — the 7:59 PM YC submission
(00:37) Intro — Davik & what Shor is (affordable global payroll)
(02:51) Waterloo → founder mindset and process discipline
(06:05) YC journey and batch dynamics
(08:26) First leap without an idea + early GTM lessons
(11:56) Marketplaces are hard — takeaways that shaped Shor
(14:56) The last-day YC rush & the crypto/fiat idea
(24:49) Pivot hell inside YC → choosing global payroll
(27:28) Shipping contractor payroll in one week + why now (AI/stablecoins)
(29:33) Fundraising wrapped; AI teammates over dashboards; what’s next

‍

Where to find Daivik Goel:

‍
Multilink: https://bento.me/daivik
LinkedIn: https://www.linkedin.com/in/daivikg
X: https://x.com/DaivikGoel
Instagram: https://instagram.com/daivikgoel
YouTube: https://m.youtube.com/channel/UCzkRfrCXIrW1v60Wyasgq7Q
Substack: https://daivikgoel.substack.com
TikTok: https://tiktok.com/@daivikgoel

‍

Where to find Shor:

‍
Website: https://tryshor.com
X: https://x.com/shor_pay
LinkedIn: https://www.linkedin.com/company/shorpay
Instagram: https://www.instagram.com/shor.pay/
YouTube: https://www.youtube.com/watch?v=OF1m1H0arYY

‍

Brought to you by:

Fondo — All-in-one accounting for startups: https://fondo.com

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1 week ago
37 minutes

Startup Growth Podcast
Cody Schneider | Growth Flywheels, Underpriced Attention & Building Graphed's AI Agent for Marketing Analytics

Cody Schneider is the Founder & CEO of Graphed, an AI agent for marketing analytics. Graphed plugs into common data sources, manages the data warehouse, and lets marketers chat with their data to generate on-demand visuals—“stacked bar of new vs. total users week over week,” “add a line of best fit,” and similar prompts. It’s built to handle scale (Cody mentions onboarding ~25M rows of Facebook data) and to avoid rate limits and sluggish queries by owning the warehousing layer.

In this episode, Cody outlines a practical path from data sprawl to decisions: skip steep BI learning curves and ticket queues; connect sources and ask in plain English for charts and basic analyses. He also talks about how creative volume now functions as targeting—ship lots of concepts, let algorithms find buyers—and positions Graphed as the way to see what’s working without waiting on a data team. For founders and marketers, it’s a clear primer on turning raw rows into faster feedback loops.

‍

Key Topics Covered:

• What Graphed is: an AI agent for marketing analytics that connects sources, manages the warehouse, and lets you chat to generate charts and basic analyses. 
• From tickets to answers: why BI queues and tool learning curves slow teams—and how a chat interface shortens time-to-insight.
• Scale as a requirement: handling large datasets (e.g., ~25M rows of ads data) and avoiding rate limits via a managed warehousing layer.
• Roadmap preview: proactive weekly Slack briefs that summarize what changed and why (future functionality).
• Creative = targeting: in 2025 paid acquisition, high-volume creative acts as the audience filter while algorithms find buyers.
• Stacking S-curves: double down on the working channel, then layer the next before growth plateaus.
• Arbitrage windows: underpriced media (e.g., creator CPMs ≈ $2; low-cost local streaming TV CPMs) and why illiquid channels create edge.
• Unit economics discipline: CAC/ARPU/LTV/payback thinking—losing on month one can be rational if LTV justifies it.
• Validation before build: use ads and landing pages to test demand—even before a product exists.
• Founder ops stack: practical setup (e.g., Stripe Atlas, Mercury, Carta, Fondo) to keep focus on product and sales.


Chapters


(00:00) Introduction to Graphed.com
(02:12) Cody's Journey at Rupa Health
(05:36) Growth Strategies and Metrics
(11:19) Paid Advertising Insights
(15:10) Exploring Programmatic TV Advertising
(18:57) The Vision Behind Graphed.com
(21:57) Building a Financial Stack for Startups


Where to find Cody Schneider:


LinkedIn: https://www.linkedin.com/in/codyxschneider

X: https://x.com/codyschneiderxx 


Where to find Graphed:

X: https://x.com/graphed
Website: https://www.graphed.com

‍

Where to find David Phillips:
‍

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips


Brought to you by:

Fondo — All-in-one accounting for startups: https://fondo.com

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2 weeks ago
23 minutes

Startup Growth Podcast
Craig J. Lewis | 750K Contractors Paid, $25M Raised, MassChallenge Board - From Gig Wage to Ogentic AI

Craig Lewis is the Founder & CEO Ogentic AI, builder of Zing—an AI-native enterprise browser that turns intent → action in a secure, workflow-native workspace. Before Ogentic, he founded Gig Wage (750k contractors paid, ~$1B moved, $25M+ raised) and learned payroll inside ADP. That operator muscle fuels Ogentic’s pace: incorporated in June, alpha in July, beta in August. He also serves on the governing board at MassChallenge and angels actively.

In this episode, Craig shares velocity advice like: ship before perfect (feedback > stealth), build pro-human AI (human-in-the-loop), and treat fundraising like sales (expect 19 no’s, optimize investor–founder fit, when it’s right—TTFM). He outlines the back-office stack that keeps your startup in good shape and his board philosophy: offer perspective, not prescriptions. If you’re building enterprise AI—or just want to move in weeks, not quarters—this one’s for you.


Key Topics Covered:

  • Ogentic AI focuses on enterprise productivity and automation.
  • Building a strong back office is crucial for startups.
  • Fundraising is a numbers game; persistence is key.
  • Feedback is essential for product development.
  • AI will replace some jobs but also create new ones.
  • Having a technical co-founder can accelerate growth.
  • Navigating the fundraising landscape requires understanding investor fit.
  • MassChallenge supports entrepreneurs in solving global challenges.
  • The future of work will involve augmenting human capabilities with AI.
  • Startups should find their niche in the AI market.


Chapters

(00:00) The Rise of Ogentic AI

(13:37) Building a Strong Back Office

(17:02) Navigating Fundraising Challenges

(19:14) The Role of MassChallenge

(23:12) AI and the Future of Work

(27:40) Fundraising in the AI Era


Where to find Craig J. Lewis:

Linkedin: https://www.linkedin.com/in/mrfutureofwork

X: https://x.com/CraigJamalLewis 

Instagram: https://www.instagram.com/craigjlewis


Where to find Ogentic AI:

 
Website: https://ogenticai.com
LinkedIn: https://www.linkedin.com/company/ogenticai
X: https://x.com/ogenticai
Instagram: https://www.instagram.com/ogenticai

‍

Where to find David Phillips:
‍

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips


Brought to you by:

Fondo — All-in-one accounting for startups: https://fondo.com

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2 weeks ago
31 minutes

Startup Growth Podcast
Grace Gong | Lessons on Building Founder–Investor Community: Curate for Outcomes, Not Optics

Grace Gong is the Founder & CEO of Smart Venture Media, podcast host, angel investor, and author. She’s interviewed 500+ founders, investors, and operators on her podcasts, then parlayed that network into a high-signal community: curated founder–VC dinners, conferences (including the Smart AI Summit), and rooms where intros turn into customers and checks. The flywheel started during the pandemic with 5 pm Friday Zooms—and evolved into tightly curated IRL events supported by sponsors and operators.

In this episode, Grace outlines a practical approach to community-building: curate for outcomes, not optics (every seat should benefit from every other seat). Her angel filter doubles as her invite list. Online → IRL is the sequence: earn trust digitally, concentrate it offline.  For founders aiming to stand out without burning cash, this is a clear primer on turning audience into deal flow.

‍

Key Topics Covered:

  • Building community has to happen organically.
  • Engaging with entrepreneurs can lead to unexpected opportunities.
  • Sales and storytelling are crucial skills for success in VC.
  • Offering value to others is key to building relationships.
  • The people you meet at events can significantly impact your journey.
  • Planning events requires meticulous attention to logistics.
  • Creating a curated experience enhances networking opportunities.
  • AI is transforming the media landscape and how we build companies.
  • Networking is essential for both founders and investors.
  • Continuous learning and adaptation are vital in the fast-paced tech world.


Chapters

(00:00) Building Community: The Organic Approach
(02:50) Journey into Venture Capital: From Real Estate to VC
(05:44) Insights from Interviews: Lessons Learned in VC
(08:53) Angel Investing: Key Considerations
(11:51) Creating Value: The Importance of Community
(15:02) Event Planning: From Small Gatherings to Large Conferences
(17:59) The Smart AI Summit: Curating Experiences
(20:54) Future of Media: Building with AI
(23:48) Final Thoughts and Online Presence


Where to find Grace Gong & Smart Venture Media:


Linktree: https://linktr.ee/gracegong115

‍

Where to find David Phillips:
‍

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips


Brought to you by:

Fondo — All-in-one accounting for startups: https://fondo.com

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3 weeks ago
27 minutes

Startup Growth Podcast
Collin Wallace: Inside venture funds, why billion-dollar outcomes make sense - and how founders stack the odds

Collin Wallace is a partner at Lobby Capital with 20+ years as an engineer, inventor, operator, and investor. Before Lobby, he was Managing Director of Techstars Silicon Valley, launching the first two Bay Area accelerator programs with JPMorgan and eBay. He founded FanGo (Techstars S10)—acquired by Grubhub in 2011, where he became Head of Innovation (OrderHub + pre-IPO patents)—and later co-founded ZeroStorefront (YC W19), acquired by Thanx in 2022. Collin advises the Roelof Botha & Huifen Chan Innovation Program, co-teaches Startup Garage at Stanford GSB, has run two YC Demo Day Funds, and has invested in 80+ startups (e.g., Payjoy, Landed, Mosaic Voice, Postscript, Vellum).

In this episode, Collin gives founders some great advice: you’re running two businesses (product for customers, equity for investors). Fund math in concentrated portfolios means ~2 of ~20 bets must carry returns; with dilution to ~10% at exit, winners need multi-billion-dollar potential. Sequence your proof: Pre-seed = prove value; Seed = prove people pay (repeatably); Series A = scale what’s already repeatable. Don’t scale misses (the Steph Curry test). And match capital to your vehicle - venture is rocket fuel: perfect for rockets, destructive for "pickup trucks".


Key Topics Covered:

  • Running a startup involves selling to customers and investors.
  • Different VCs have varying expectations based on fund size and strategy.
  • Founders should tailor their pitches to the specific needs of investors.
  • Understanding investor dynamics can improve fundraising success.
  • Successful founders diverge from conventional thinking in their industries.
  • Ambition and hustle are key traits for founders.
  • Expectations change significantly after receiving funding.
  • Consistency and repeatability are crucial for scaling a startup.
  • Community engagement can foster innovation and collaboration.
  • The back office is essential but often seen as a distraction.

Chapters

(00:00) Introduction to Colin Wallace and His Journey
(02:14) The Shift in Growth Expectations for Startups
(05:03) Understanding Investor-Fit and Fundraising Dynamics
(11:12) The Importance of Founder Attributes
(17:15) Navigating the VC Landscape and Expectations
(21:03) Post-Funding Realities for Founders
(22:40) Understanding Seed Capital and Series A Expectations
(25:19) The Evolution of Funding: Series B and C
(29:05) Coaching the Next Generation of Founders
(32:09) Building the Back Office: The Unsung Hero
(35:42) Community Building and Inclusive Events

Where to find Collin Wallace:

‍

Linkedin: https://www.linkedin.com/in/collin-wallace/ 

X: https://x.com/pithyprof 

Website: https://lobby.vc/people/collin-wallace/ 

‍

Where to find Lobby Capital:
Linkedin: https://www.linkedin.com/company/lobby-capital/
X: https://x.com/lobby_vc
Website: https://lobby.vc/

‍

‍

Where to find David Phillips:

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips


Brought to you by:


Fondo — All-in-one accounting for startups: https://fondo.com

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3 weeks ago
44 minutes

Startup Growth Podcast
Alessandro Chesser: Turn Founder Shares into Tax‑Free Gains with QSBS Trust Stacking

Alessandro Chesser is the founder and CEO of Dynasty, a startup focused on making Qualified Small Business Stock (QSBS) trust stacking accessible to founders. Before launching Dynasty, he led sales at Carta from the early days to roughly $300M in ARR, gaining hands-on insight into equity workflows, 409A dynamics, and how distribution is built around real, recurring needs. Dynasty offers a subscription service—$1,500 per year for up to four family trusts—that includes trust creation, annual administration, and tax return filing, turning a traditionally bespoke, high-cost process into something founders can set up early in their journey.

In this episode, we unpack the mechanics and timing that make—or break—QSBS outcomes. We cover the core tests (acquiring shares before $50M in assets, five-year hold, qualified C-corp status), state-level differences (New York recognizes QSBS; California does not), and why early planning can start both the QSBS and long-term capital gains clocks while avoiding later surprises. 

Chesser talks about trust stacking—gifting shares into multiple family trusts so each may pursue its own QSBS exclusion—and notes practical guardrails and expert advice for dong it right. Beyond the tax planning, Chesser shares go-to-market lessons from Carta and Dynasty: using the network effect (e.g., certificates signed), creating urgency with must-do workflows (like 409A), iterating growth levers monthly, hiring decisively, and using social + creator partnerships instead of traditional cold outbound. The result is clear: tactical advice for founders on when to exercise, when to gift, how to document, and how to avoid the common QSBS pitfalls discussed in the conversation.

‍

Key topics covered

- QSBS allows startup shareholders to sell up to $15 million tax-free.
- Most startups qualify for QSBS, but there are specific criteria.
- Holding shares for at least five years is crucial for QSBS eligibility.
- The new rules under the big beautiful bill change QSBS eligibility timelines.
- Dynasty helps founders maximize QSBS benefits through trust stacking.
- Early exercise of stock options can prevent alternative minimum tax issues.
- Filing an 83B election is essential for QSBS qualification.
- Social media is a powerful tool for startup growth and marketing.
- Building partnerships with influencers can enhance visibility and credibility.
- The cost of setting up trusts for QSBS is significantly lower with Dynasty.

‍

In This Episode, We Cover

(00:00) Introduction to QSBS and Its Importance

(06:35) Understanding QSBS Eligibility and Benefits

(13:08) The Role of Dynasty in Maximizing QSBS Benefits

(16:29) Alessandro's Journey and the Birth of Dynasty

(18:36) Growth Strategies and Lessons from Carta

(27:14) Leveraging Social Media for Growth

‍

Where to Find Alessandro Chesser:

‍

LinkedIn: https://www.linkedin.com/in/alessandro-chesser-84763748

X: https://x.com/SandroChess

‍

Where to Find Dynasty:

‍

Website: https://www.getdynasty.com

LinkedIn: https://linkedin.com/company/getdynasty

X: https://x.com/getdynasty_com

‍

Where to Find David Phillips:

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips

Brought to you by:

Fondo — All-in-one accounting for startups: https://fondo.com

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1 month ago
33 minutes

Startup Growth Podcast
Jeff ‘Jiho’ Zirlin: From 300 Users to $4B+ in Trading Volume, The Story Behind Axie Infinity’s Meteoric Growth

Jeff ‘Jiho’ Zirlin is a co-founder of Sky Mavis, the team behind Axie Infinity and the Ronin blockchain. At the forefront of Web3's most groundbreaking experiments, Jeff helped transform Axie from a small crypto-native community into a cultural phenomenon that onboarded millions to blockchain technology. With over $4 billion in NFT trading volume - earning a Guinness World Record - Axie didn't just talk about bringing people to crypto; it actually did it. Beyond Axie, Jeff pioneered the Ronin blockchain, which now hosts 70+ games and has proven that purpose-built infrastructure can unlock exponential growth for crypto applications.


In this episode, we trace the evolution of Web3 gaming from its origins in the CryptoKitties community to today's institutional adoption cycle. The conversation explores how manual onboarding and white-glove user acquisition laid the foundation for viral growth. Jeff shares the pivotal moments that shaped Axie's trajectory: tokenizing experience points, creating the "play-to-earn" model that democratized crypto mining, and the strategic decision to build their own blockchain when existing infrastructure couldn't scale. We also examine the current state of crypto gaming, the shift from retail mania to Wall Street adoption, and why the next wave of innovation might create entirely new cultural mediums rather than just new ways to make money.



Key topics covered:

  • The CryptoKitties Mafia: How a December 2017 viral game spawned the founders of Axie, OpenSea, and the modern NFT ecosystem
  • Manual onboarding at scale: From personally gifting Axies to Binance angels to hitting 2 million users
  • The biological insight: Why CryptoKitties failed (no death = exponential breeding) and how ecosystem balance became Axie's core principle
  • 300 users was "#1": How being the largest crypto game with just 300 players became a marriage proposal line - and a growth trajectory
  • Tokenizing the game economy: The moment players asked to buy experience points and accidentally invented play-to-earn
  • "You can't build your startup on another startup": Why Loom Network's failure forced Sky Mavis to create Ronin blockchain
  • The Ronin Effect: Deploying at 30,000 users, scaling to 2 million in six months - and the infrastructure playbook now powering 70+ games
  • The Uniswap wealth effect: How every Axie player unexpectedly received $4,000, creating a growth catalyst nobody predicted
  • Why gaming onboards better than DeFi: More people game than trade - and nostalgia beats complexity when introducing scary new technology
  • From Binance to NYSE: This cycle's institutional meta and why crypto gaming hasn't figured out Wall Street yet
  • The new Renaissance: How fractional reserve banking created the actual Renaissance, and why crypto's lasting impact will be cultural, not financial
  • Loyalty programs vs. helicopter money: Evolving from infinite money glitches to targeted behavioral incentives
  • 70+ economic experiments: From AI-powered tanuki battles to on-chain "Runescape" - why only one or two need to work
  • The cypherpunk optimism: Why crypto offers a more definite, grounded vision for the future than AI or robotics


Where to find...

Jeff 'Jiho' Zirlin:

  • Instagram: https://www.instagram.com/axieinfinity
  • X: https://x.com/Jihoz_Axie
  • LinkedIn: https://www.linkedin.com/in/jeffzirlin

Skymavis:

  • Website: https://skymavis.com
  • Instagram: https://www.instagram.com/axieinfinity
  • X: https://x.com/skymavishq
  • LinkedIn: https://www.linkedin.com/company/skymavis


Axie 

  • Website: https://axieinfinity.com/
  • Instagram: https://www.instagram.com/axieinfinity
  • X: https://x.com/AxieInfinity
  • LinkedIn: https://www.linkedin.com/company/axieinfinity


Ronin

  • Website: https://roninchain.com
  • Instagram: https://www.instagram.com/axieinfinity
  • X: https://x.com/ronin_network 
  • LinkedIn: https://x.com/ronin_network


David Phillips:

  • Website: www.fondo.com
  • Instagram: https://www.instagram.com/axieinfinity
  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips


In This Episode, We Cover


(00:00) From 300 to thousands of Users: The Binance Effect

(17:41) Community-Driven Growth: The Role of Guilds

(18:38) Experimentation as a Growth Strategy

(19:52) Challenges and Advantages in Crypto Growth

(20:03) Learning Through Gaming: Onboarding to Crypto

(21:27) The Uniswap Airdrop: A Catalyst for Growth

(22:18) Onboarding and Scaling in Crypto Gaming

(23:17) The Ronin Network: A Solution for Scalability

(24:40) The Evolution of Ronin and Its Community

(25:10) Expanding the Ronin Ecosystem: New Games and Innovations

(27:02) Economic Experiments in Crypto Gaming

(28:56) The Cultural Renaissance of Crypto

(30:14) Future Innovations in Web3 Gaming

(31:36) Optimism for the Future of Crypto

Brought to you by:

Fondo — All-in-one accounting for startups: https://tryfondo.com

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1 month ago
35 minutes

Startup Growth Podcast
Parthi Loganathan: Beyond Cold Outbound - How Letterdrop Transforms Intent Signals Into Revenue Opportunities

Parthi Loganathan is the founder and CEO of Letterdrop, a Y Combinator-backed startup that helps B2B companies build pipeline by focusing on the warmest leads and people who are actually in market. Since launching Letterdrop, he's helped companies move beyond saturated email and cold calling tactics to identify prospects who want to talk and send them highly tailored messaging. The platform analyzes public conversations, CRM data, and sales calls to segment buyers and enable personalized outreach without relying on high-volume approaches.


In this episode, we explore the fundamental shift happening in B2B sales as traditional cold outbound becomes less effective and companies invest in higher-effort tactics to stand out. The conversation covers the evolution from Letterdrop's origins as an SEO tool to its current focus on conversation intelligence, driven by market changes from ChatGPT's emergence. Parthi shares insights about the three essential components of effective outbound messaging, why customer conversations represent untapped content goldmines, and his firsthand experience being demoed by an AI sales agent. We also examine his predictions about AGI's timeline and the philosophical question facing all founders: do you build for today's market or tomorrow's technological reality?


Key topics covered:

  • Why cold email reply rates dropped 40% in 2024 and the shift away from "spam your TAM" tactics
  • The reality that only 2-3% of your market wants to purchase at any given time
  • Three components of effective outbound: solid observation, poking the P0 problem, and value-first offers
  • Letterdrop's strategic pivot from SEO tools to conversation intelligence as ChatGPT emerged
  • How customer and prospect conversations contain unique content that competitors can't replicate
  • The founder journey from Google product manager through multiple micro-SaaS startups to YC
  • Real experience with an AI AE conducting demos better than human salespeople
  • Why "marinating" in a single problem space beats jumping between different markets
  • The philosophical choice between building Cursor (for today) versus Anthropic (for the future)
  • AGI timeline predictions and whether UBI will arrive before widespread job displacement

Where to find Parthi Loganathan:


Linkedin: https://www.linkedin.com/in/parthiloganathan/

X: https://x.com/parthi_logan


Where to find Letterdrop:


Website: https://letterdrop.com/

Linkedin: https://www.linkedin.com/company/letterdrop/

X: https://x.com/letterdropco

Podcast: https://open.spotify.com/show/43bSCi3FcFaJ28H7qEK59X?si=2f6afe15cea342ea

Where to Find David Phillips:

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips/


In This Episode, We Cover


(00:00) Introduction to LetterDrop and Its Mission
(02:52) The Evolution of Outbound Sales Strategies
(06:11) Crafting Effective Outbound Messages
(09:09) Parthi's Journey as a Founder
(12:02) Leveraging Social Conversations for Sales
(14:59) Creating Content from Customer Conversations
(17:55) Back Office Operations for Startups
(20:49) The Role of AI in Sales
(23:38) The Future of Work: AGI and UBI
(26:46) Closing Thoughts and Future Questions


Brought to you by:

Fondo — All-in-one accounting for startups: https://tryfondo.com


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1 month ago
31 minutes

Startup Growth Podcast
John Paul Mussalli: How One EMT's Scrappy Prototype Evolved Into an AI Tool That Won Over 20% of NYC's EMTs

In this episode, I sat down with John Paul Mussalli, the co-founder and COO of CareSwift, a Y Combinator-backed startup building AI-powered software to streamline documentation for EMT workers. 

JP and his cofounders brings a unique blend of technical expertise and entrepreneurial drive to the healthcare technology space, having previously worked across diverse fields from real estate automation to web development. 

Since co-founding CareSwift, he's helped scale the platform to serve over 2,000 EMTs in New York City alone, generating more than 90,000 automated reports. Beyond product development, JP leads go-to-market strategy and is currently pursuing EMT certification himself to deepen his understanding of the industry's challenges.

In this episode, we explore the journey from scrappy prototype to venture-backed startup and the critical lessons learned along the way. 

Key topics covered:

  • How a ChatGPT prototype evolved into a venture-backed healthcare AI platform
  • The hidden costs of poor EMT documentation: $1,800 per error and 11% industry revenue loss
  • Why 25% of New York's EMTs organically adopted CareSwift without marketing
  • Critical incorporation mistakes that can delay funding and how to avoid them
  • The strategic decision to expand from narrative reports to full documentation workflow
  • Why domain expertise matters when building AI for specialized industries
  • Navigating regulatory compliance and the founder stack for healthcare startups
  • The reality of Y Combinator: 996 work culture and rapid iteration cycles
  • From 15-20 minute reports to 2-minute automated workflows saving hours per shift
  • Why sometimes a bug in Apple Mail can redirect your entire startup journey


Where to find John Paul Mussalli 


- Linkedin: https://www.linkedin.com/in/jpmussalli/
- X: https://x.com/jpm1126


Where to find CareSwift:


- Website: https://careswift.ai/

- Linkedin: https://www.linkedin.com/company/careswift/

Where to Find David Phillips:

- X: https://x.com/davj

- LinkedIn: https://www.linkedin.com/in/davjphillips/


In This Episode, We Cover


(00:00) Introduction to CareSwift and Its Founders

(02:54) The Birth of CareSwift: Addressing EMT Challenges

(06:09) Impact of CareSwift on EMT Efficiency

(09:01) Navigating the Startup Journey: Lessons Learned

(09:35) Navigating Startup Structures and Legalities

(12:14) The Journey Through Y Combinator

(15:06) Daily Life as a Founder in Y Combinator

(17:13) Building a Founder Stack: Tools and Resources

(18:57) Future Plans

Brought to you by:

Fondo — All-in-one accounting for startups: https://tryfondo.com


Show more...
1 month ago
21 minutes

Startup Growth Podcast
Reuben Torenberg: Inside SF's Office Market Comeback: Deals, Trends & AI Company Growth

Reuben Torenberg is a Senior Vice President at CBRE, the world's largest commercial real estate services firm. Reuben specializes in helping startups in San Francisco navigate the complex and rapidly changing office leasing landscape. Since joining CBRE in 2014, he's represented some of the biggest names in tech - including Airbnb, Coinbase, Cruise, and Dropbox - and is widely known as the go-to broker for early-stage startups and growth-stage companies alike. Beyond real estate, Reuben is also a community builder, having founded SF Hoops and SF Links, two of the city's most exclusive and founder-heavy social sports leagues.

In this episode, we explore the dramatic transformation of San Francisco's commercial real estate market and the evolving dynamics between landlords, tenants, and the broader tech community. The conversation delves into current market trends in both office and retail spaces, examines how AI companies are reshaping demand patterns, and discusses the critical importance of community building in the tech industry through initiatives like SF Hoops. We also dive deep into pricing strategies, emerging market opportunities, and provide a comprehensive outlook for businesses seeking space in San Francisco.


Topics covered:

  • Why SF's commercial real estate recovery is finally here after 5 years of decline
  • How AI companies are driving massive demand and changing the market dynamics
  • Where to find the best deals: neighborhood analysis and sweet spot sizing (10-20K sq ft)
  • Why rents are rising and landlords are getting more confident by the day
  • Buildings selling at 80% discounts and what it means for new opportunities
  • The return-to-office mandate trend and its impact on space demand
  • Lower SoMa as the last frontier for deeply discounted office space
  • Retail space conversion opportunities in Union Square
  • Why you should secure space now vs. waiting for better deals
  • Pricing breakdown: what 10, 25, and 50-person companies should budget
  • How to navigate the search process and when to use a broker
  • & Much more


Where to Find Reuben Torenberg:

CBRE: https://www.cbre.com

X: https://x.com/RTorenberg021

LinkedIn: https://www.linkedin.com/in/reuben-torenberg-b985b646


Where to Find SF Hoops:
https://sfhoopsleague.com

https://x.com/SFHoopsleague


Where to Find David Phillips:

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips/


In This Episode, We Cover

(00:00) Current Trends in San Francisco Commercial Real Estate

(02:53) Navigating the Market: Opportunities and Challenges

(05:54) The Shift in Office Space Demand

(08:43) Retail Space and Its Transformation

(11:55) Landlord Strategies and Market Dynamics

(14:52) The Rise of SF Hoops: Networking Through Sports

(17:59) Future Outlook: What to Expect in the Coming Months

Brought to you by:

Fondo — All-in-one accounting for startups: https://tryfondo.com

Show more...
1 month ago
27 minutes

Startup Growth Podcast
Stephen Llevano: The Founder Journey, Startup Surprises, and Takeaways for Every Founder

Stephen Llevano is the founder and CEO of Capabuild, where he helps insurance contractors navigate complex compliance requirements through innovative software solutions. With deep expertise in the insurance contracting space, Stephen specializes in compliance management, operational efficiency, and helping growing contractors optimize their business operations while managing regulatory challenges.

In this episode, Stephen breaks down his journey from "reluctant entrepreneur" to building successful compliance management software, particularly the game-changing insights about truly understanding customer needs and how contractors can leverage proper compliance tools to streamline their operations and focus on growth.

We explore the challenges that traditional compliance methods have created for contractors and dive into practical strategies for navigating these changes, including when direct customer observation makes sense and how to leverage evolving pricing strategies and operational improvements. Stephen also explains the powerful long-term benefits of supporting local service businesses and the importance of building strong community relationships for sustainable growth.

Check out Capabuild:

  • https://www.capabuild.app/
  • https://apps.apple.com/us/app/capabuild/id1642228115
  • https://play.google.com/store/apps/details?id=com.capabuild.app&pcampaignid=web_share


Brought to you by:

  • Fondo — Automate your accounting and unlock up to $500k from the IRS: tryfondo.com

Where to find Stephen Llevano

  • X: https://x.com/StephenLlevano
  • LinkedIn: https://www.linkedin.com/in/stephen-llevano/


Where to Find David Phillips

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/


Takeaways

  1. Connecting directly with customers as a founder is crucial for product success
  2. Observing customers in their actual work environment reveals true needs beyond feedback
  3. Pricing strategies must evolve based on real customer insights and market dynamics
  4. Building a startup requires more time and emotional investment than initially expected
  5. The insurance industry is shifting, creating new opportunities for adaptive contractors
  6. Personal relationships often drive initial customer acquisition and business development
  7. Deep market understanding is essential for navigating industry complexities
  8. Operational efficiency directly impacts a contractor's ability to serve clients effectively
  9. Supporting local service businesses creates stronger community economic foundations
  10. Every entrepreneurial experience offers valuable learning opportunities worth embracing


Chapters

  • (00:01) The Entrepreneur's Journey
  • (03:03) Identifying Market Opportunities
  • (05:55) Building the First Version of Capabild
  • (08:51) Customer Acquisition and Pricing Strategies
  • (11:57) The Evolution of Capabuild
  • (20:56) Operational Challenges and Solutions
  • (23:51) Future of the Industry and Capabild's Mission
Show more...
2 months ago
31 minutes

Startup Growth Podcast
Saving Startups Millions, R&D Credit Deep Dive, and Breaking Down the Big Beautiful Bill: Jake Wedig

Jake Wedig is the Director of Tax at Fondo, where he helps startups navigate complex tax legislation and maximize their tax benefits. With deep expertise in startup tax strategy, Jake specializes in R&D tax credits, Section 174 compliance, and helping growing companies optimize their tax positions while managing cash flow challenges.

In this conversation, Jake breaks down the recent changes in tax legislation that every startup founder needs to know about, particularly the game-changing provisions in the One Big Beautiful Bill and how startups can leverage R&D tax credits to get substantial cash back on their development investments.


We explore the challenges that Section 174 has created for startups and dive into practical strategies for navigating these changes, including when amending tax returns makes sense and how to leverage bonus depreciation and Section 179 deductions. Jake also explains the powerful long-term benefits of Qualified Small Business Stock (QSBS) for founder wealth optimization.


Key topics covered:

  • How the One Big Beautiful Bill creates new tax optimization opportunities for startups
  • Maximizing R&D tax credits for substantial cash returns on development investments
  • Navigating Section 174's impact on R&D expense deductions and cash flow management
  • Strategic use of amended returns to recover from unexpected tax positions
  • Leveraging bonus depreciation and Section 179 for immediate equipment deduction benefits
  • Understanding QSBS benefits and the five-year holding period requirements
  • The importance of proactive tax planning partnerships between startups and advisors
  • Staying ahead of evolving tax legislation to capture emerging opportunities
  • And much more

Brought to you by:

  • Fondo — Automate your accounting and unlock up to $500k from the IRS: https://tryfondo.com

Where to find Jake Wedig


  • LinkedIn: https://www.linkedin.com/in/jacob-wedig

Where to Find David Phillips

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/

In This Episode, We Cover

  • (01:42) Understanding the New Tax Bill
  • (03:31) R&D Tax Credits and Their Importance
  • (07:51) Impact of Section 174 on Startups
  • (13:05) Amending Returns and Cash Flow Considerations
  • (07:10) Lessons from a slow death and how to move on
  • (16:38) The Role of Tax Advisors for Startups
  • (30:55) Bonus Depreciation and Section 179
  • (35:23) Qualified Small Business Stock (QSBS) Benefits
Show more...
2 months ago
39 minutes

Startup Growth Podcast
Nathan Latka: Bootstrapping to $2M ARR, Turning Down $6.5M, and Funding 500+ Startups

Nathan Latka is the founder and CEO of Founderpath, a fintech platform that has deployed nearly $200 million in non-dilutive capital to 500+ software companies. He’s also the creator of GetLatka, a massive SaaS database built off the back of his top-ranked Latka podcast, where he’s interviewed thousands of founders. Nathan’s entrepreneurial journey began at 18 with the launch of Heyo, a Facebook fan page SaaS tool he bootstrapped to $2M in ARR before raising venture capital and eventually exiting.

In this conversation, Nathan shares hard-earned lessons from building and exiting companies, explains why most founders don’t understand the true cost of raising VC, and offers a compelling case for why debt and secondaries can be a smarter option. We also explore:

  • How he bootstrapped Heyo to $2M ARR before raising VC
  • The $6.5M exit offer he had to turn down (and regrets)
  • What most founders misunderstand about venture capital
  • How GetLatka became the #1 ranked SaaS benchmarking database
  • Why the future belongs to tiny teams with huge revenue
  • The three AI trends shaping SaaS company formation
  • How FounderPath prices startup equity daily—instantly enabling secondaries
  • Why hooks and attention matter more than ever
  • And much more

Brought to you by:

  • Fondo — Automate your accounting and unlock up to $500k from the IRS: https://TryFondo.com

Where to Find Nathan Latka

  • X: https://x.com/NathanLatka
  • Instagram: https://www.instagram.com/nathanlatka/
  • LinkedIn: https://www.linkedin.com/in/nathanlatka/
  • Podcast: Latka Podcast
  • SaaS Database: https://getlatka.com
  • Book: How to Be a Capitalist Without Any Capital

Where to Find David Phillips

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/

In This Episode, We Cover

  • (00:00) Intro to Nathan and FounderPath
  • (01:30) The story behind Heyo and bootstrapping to $2M ARR
  • (03:50) Raising venture and losing optionality
  • (05:30) The $6.5M offer and why his board said no
  • (07:10) Lessons from a slow death and how to move on
  • (08:15) Why Nathan started the Latka podcast
  • (09:30) Building GetLatka to 3,000+ daily organic clicks
  • (11:00) The power of hooks and attention in modern SaaS
  • (12:45) Inside FounderPath: non-dilutive capital for SaaS
  • (14:30) How venture debt differs from traditional VC
  • (16:15) Why secondaries are healthy, not harmful
  • (18:00) How FounderPath prices startup equity daily
  • (20:10) Big trends: tiny teams, chat-based dashboards, attention > tech

Referenced

  • GetLatka – https://getlatka.com
  • FounderPath – https://founderpath.com
  • Heyo (archived) – https://en.wikipedia.org/wiki/Heyo
  • How to Be a Capitalist Without Any Capital (Book) – https://www.amazon.com/How-Be-Capitalist-Without-Capital/dp/0525534440
  • ZoomInfo – https://www.zoominfo.com
  • Techstars – https://www.techstars.com
  • G2 Crowd – https://www.g2.com
Show more...
5 months ago
18 minutes

Startup Growth Podcast
Selling Before You’re Ready: How Early Stage Founders Close Their First Customers

Ajith Govind and Avinash Joshi are the co-founders of Cactus, an AI copilot for solopreneurs such as private chefs and caterers, helping them streamline admin tasks and grow their business. Brian Kuan, Community Manager at Vanta, hosted the conversation. Together, we explore early-stage sales, building trust, and the YC network's unique power to catalyze startup momentum. In this episode, we discuss:

  • Why founder-led sales is irreplaceable
  • Leveraging Bookface and social media for early traction
  • Building trust with SMBs and solopreneurs outside your network
  • Cold outreach tactics that actually worked
  • Why you should launch even a half-baked product
  • The underestimated power of urgency in early sales
  • Stories behind onboarding first customers at Fondo and Cactus
  • The emotional moments that proved they were building something impactful
  • How fundraising and selling are deeply intertwined
  • Much more

Brought to you by:

  • Fondo — All-in-one accounting for startups: https://fondo.com


Where to Find David Phillips

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/

Where to Find the Guests:


Brian Kuan (Vanta, W18)

  • LinkedIn: linkedin.com/in/briankuan

Ajith Govind (Cactus, X25)

  • X: x.com/itsajith747
  • LinkedIn: linkedin.com/in/ajith-govind

Avinash Joshi (Cactus, X25)

  • X: x.com/avinashjoshi
  • LinkedIn: linkedin.com/in/joshi-avinash

Where to Find the Companies

  • Cactus: x.com/oncactusai | LinkedIn
  • Fondo: fondo.com
  • Vanta: x.com/TrustVanta | LinkedIn

In This Episode, We Cover

  • (00:00) Introductions and what each company does
  • (03:12) How Fondo found its first customer through a cold DM to Sam Parr
  • (05:40) How Cactus began by solving a personal need with personal chefs
  • (09:05) Using Bookface to unlock growth
  • (13:00) Tips for selling to startups and SMBs
  • (16:45) How product-led growth and founder empathy drive traction
  • (20:18) Balancing building with selling as a founder
  • (25:12) Founder-led sales vs. traditional sales teams
  • (28:00) How trust is built—especially outside your network
  • (32:40) Lightning Round: first big sales wins, boldest cold DMs, best YC perks
  • (38:35) Sales tactics they wish they knew on Day 1
  • (41:00) Fundraising urgency and investor psychology

Referenced

  • Sam Parr (The Hustle): https://www.thehustle.co
  • PostHog: https://posthog.com
  • Bookface (YC Internal Network): https://www.ycombinator.com
  • Brex: https://www.brex.com
  • Christina Cacioppo (CEO, Vanta): LinkedIn
  • Marketplace Capital: https://marketplacecapital.vc
  • YC Demo Day: https://www.ycombinator.com/demo-day
Show more...
5 months ago
41 minutes

Startup Growth Podcast
From Overpriced to Undervalued: Why Now is the Time for Startups to Get in on SF's Real Estate Deals

Reuben Torenberg is a First Vice President at CBRE, the world’s largest commercial real estate services firm. Reuben specializes in helping startups in San Francisco navigate the complex and rapidly changing office leasing landscape. Since joining CBRE in 2014, he's represented some of the biggest names in tech — including Airbnb, Coinbase, Cruise, and Dropbox — and is widely known as the go-to broker for early-stage startups and growth-stage companies alike. Beyond real estate, Reuben is also a community builder, having founded SF Hoops and SF Links, two of the city’s most exclusive and founder-heavy social sports leagues.

In this episode, we dive into the state of commercial real estate for startups in 2025, including:

  • Why SF is now a tenant’s market — and what that means for startups
  • How to find cheap, high-quality office space (and avoid costly mistakes)
  • How much space your startup really needs at each stage
  • Why brokers are free for tenants — and why every founder should use one
  • Where the best startup neighborhoods are in SF right now
  • How coworking has evolved — and why it's a smart move for teams <10
  • What landlords are offering in TI (tenant improvement) allowances today
  • How much to offer below list — and why you should always send multiple proposals
  • The return of Class A space and what’s happening in Mission Bay, Hayes Valley, and Jackson Square
  • Much more

Brought to you by:

  • Fondo — All-in-one accounting for startups: https://tryfondo.com

Where to Find Reuben Torenberg

  • CBRE: https://www.cbre.com
  • X: https://x.com/RTorenberg021
  • LinkedIn: https://www.linkedin.com/in/reuben-torenberg-b985b646/

Where to Find David Phillips

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/

In This Episode, We Cover

  • (00:00) Intro to Reuben and CBRE
  • (01:30) From sports to real estate: Reuben’s career path
  • (03:15) Lessons from Custom Spaces and early startup deals
  • (04:50) Major tenants Reuben’s worked with: Airbnb, Coinbase, Cruise
  • (06:30) How SF Hoops became a startup founder hub
  • (08:05) SF Links and the evolution of social networking for tech
  • (09:40) How startups actually find space in SF
  • (11:00) What tenant brokers do and why they’re free
  • (13:00) Square footage per employee and planning for growth
  • (15:00) COVID's impact: SF market shift explained
  • (17:30) Class A space demand and the "flight to quality"
  • (19:45) Leasing terms, TI allowances, and negotiation tips
  • (23:00) Market insights from Q1 2025: 2.9M sq ft leased
  • (25:15) Hottest neighborhoods: Mission Bay, Jackson Square, and beyond
  • (28:00) Best advice for founders raising and scaling: flexibility, furnished space, subleases
  • (30:00) Budgeting by headcount: ballpark lease costs for 5, 10, and 25-person teams
  • (32:00) Final takeaways and next steps

Referenced

  • CBRE San Francisco Office Market Report Q1 2025 (search: “CBRE SF Q1 2025 report”)
  • LoopNet — Office space listings
  • Industrious — Premium coworking
  • Mindspace
  • Canopy
  • WeWork
  • OpenAI HQ in Mission Bay
  • Mission Rock Development — Home to Visa and the Warriors
Show more...
5 months ago
35 minutes

Startup Growth Podcast
He Built Mafia Wars to $10M a Day and Now Makes Bets on 130+ Startups

Roger Dickey is a serial entrepreneur and prolific angel investor with over 130 startup investments under his belt. From humble beginnings coding games as a kid to building Mafia Wars at Zynga—a game that reached a $300 million annual run rate—Roger has scaled multiple companies and exited to giants like Zynga, Home Depot, and private equity. He's also pioneered the "search lab" approach to company building, a structured yet high-velocity process for launching and validating startup ideas. In this episode, we cover:

  • Roger’s early obsession with coding and games
  • How Dope Wars turned into a breakout Facebook game success
  • The origin and explosive growth of Mafia Wars at Zynga
  • Building a startup that scaled to $100K/day in revenue
  • The matrix method for startup idea generation
  • Why distribution, not code, is today’s biggest moat
  • Why he believes in going deep on one growth channel
  • Lessons learned from two successful search labs
  • The importance of knowing when a product isn't working
  • What he's exploring now across SaaS, games, and social
  • Much more

Brought to you by:

  • Fondo – Accounting for startups: https://www.tryfondo.com

Find the transcript at: https://www.tryfondo.com/podcast (or wherever you're hosting it)

Where to Find Roger Dickey

  • X: https://x.com/rogerdickey
  • LinkedIn: https://www.linkedin.com/in/rogerdickey/
  • Essay – Lessons from 2 Search Labs: https://medium.com/@rogerdickey/lessons-from-2-search-labs-fe07d0bc0fb4

Where to Find David Phillips

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/

In This Episode, We Cover

  • (00:00) Intro and Roger's startup credentials
  • (01:04) Roger’s coding origin story and first “viral” product
  • (05:01) How Dope Wars exploded on Facebook
  • (10:45) Building and scaling Mafia Wars at Zynga
  • (16:00) Product-led growth mechanics and viral loops
  • (21:00) Inventing and reinventing distribution
  • (25:35) How Roger structured his “search lab” process
  • (31:00) Metrics and mindset for early-stage validation
  • (34:55) CAC, LTV, and cracking the S-curve of growth
  • (38:47) Scaling a $100K/day construction tech startup
  • (44:10) The role of deep focus vs. testing across channels
  • (48:05) What Roger’s building next and how he’s thinking about it

Referenced

  • Lessons from 2 Search Labs (Roger Dickey on Medium): https://medium.com/@rogerdickey/lessons-from-2-search-labs-fe07d0bc0fb4
  • Mafia Wars: https://en.wikipedia.org/wiki/Mafia_Wars
  • Dope Wars (original inspiration): https://en.wikipedia.org/wiki/Drug_Wars_(video_game)
  • Y Combinator Demo Day: https://www.ycombinator.com
  • Dropbox Growth Story: https://www.dropbox.com/business/resources/growth-story
  • Stripe Founder Story: https://stripe.com/blog/stripe-series-a
Show more...
6 months ago
37 minutes

Startup Growth Podcast
Fresh Blood in Old Insurance: How Vouch Built a Business Revolutionizing Startup Coverage

Travis Hedge is the co-founder and Chief Revenue Officer of Vouch, an insurance platform purpose-built for high-growth technology companies. After growing up around a family-owned insurance agency in Columbus, Ohio, Travis spent his early career at Nationwide Insurance and SVB Capital, where he saw firsthand the gaps in insurance for startups. He co-founded Vouch in 2018, and in just a few years, the company has scaled to nearly 6,000 customers. In our conversation, we dive into:

  • How Travis’s third-grade dream of becoming an insurance agent turned into a mission-driven startup
  • The critical moment that pushed him to found Vouch
  • The importance of founder-led sales and getting your first 20 customers
  • Why partnerships alone won't get you early traction
  • How Vouch built a full-stack insurance platform versus being a digital broker
  • The go-to-market lessons learned from Utah to nationwide expansion
  • How early hiring mistakes shaped Vouch’s sales strategy
  • How Travis thinks about demand generation and balancing inbound and outbound
  • Why domain expertise is essential in evaluating AI vendors
  • The inflection points that changed how Vouch scaled
  • How AI will reshape insurance but not eliminate the human element
  • Much more

Brought to you by:

  • Fondo — All-in-one accounting for startups: https://tryfondo.com

Where to Find Travis Hedge

  • Website: https://vouch.us
  • X: https://x.com/The_HedgeFund
  • LinkedIn: https://www.linkedin.com/in/travishedge/

Where to Find David Phillips (Host)

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/

In This Episode, We Cover

  • (00:00) Introduction to Travis and Vouch
  • (01:20) Travis’s early inspiration from his family's insurance business
  • (05:00) Lessons from Nationwide and SVB Capital
  • (10:30) The painful moment that sparked Vouch’s creation
  • (14:00) Building a startup insurance platform from scratch
  • (19:00) Getting the first 20 customers without relying on partners
  • (23:00) Lessons in early hiring and go-to-market team building
  • (27:00) How demand gen strategy evolved
  • (33:00) AI’s real role in insurance and go-to-market
  • (38:00) Big revenue and customer milestones
  • (43:00) How Vouch now serves both seed-stage startups and late-stage scale-ups
  • (47:00) How insurance mistakes can cost startups millions
  • (51:00) The best time for founders to get insurance
  • (56:00) Closing thoughts and Travis’s advice to founders

Referenced

  • Y Combinator (YC): https://www.ycombinator.com
  • Ribbit Capital: https://www.ribbitcap.com/
  • SVB Capital: https://www.svb.com/svb-capital
  • Opendoor: https://www.opendoor.com/
  • Root Insurance: https://www.joinroot.com/
  • Nationwide Ventures: https://nationwideventures.com/
  • Amplemarket (AI Sales tool): https://amplemarket.com/
  • Goodhart's Law: https://en.wikipedia.org/wiki/Goodhart%27s_law
Show more...
6 months ago
40 minutes

Startup Growth Podcast
Amazon's New Nemesis: How a 21-Year-Old Hit $1M ARR By Gaming Big Tech Engineering Interviews

Roy Lee is the 21-year-old founder and CEO of Interview Coder a breakout startup that has taken the internet by storm. In one year, Roy went from having his Harvard acceptance rescinded to building an AI tool used by thousands of aspiring developers to land jobs at companies like Amazon, Meta, and TikTok. His story — marked by risk-taking, resilience, and relentless building — has captivated millions on social media and sparked a firestorm of controversy in academia and Big Tech alike.

In this episode, we cover:

  • Why Roy's Harvard acceptance was rescinded, and how he bounced back
  • How a year of isolation turned into a coding bootcamp of one
  • Why community college is underrated — and how it shaped Roy’s founding team
  • How Interview Coder went from MVP to $10K MRR in a few months
  • The Amazon interview video that triggered a firestorm at Columbia
  • How going viral led to threats of expulsion — and Roy’s strategic response
  • Why Roy believes controversy is essential for attention
  • How the Z Fellows program changed his trajectory
  • A sneak peek into Roy’s new startup: Pike
  • Much more

Brought to you by:

  • Fondo — All-in-one accounting platform for startups. Bookkeeping, taxes, and cash back from the IRS: https://trifondo.com

Where to Find Roy Lee

  • X: https://x.com/im_roy_lee
  • LinkedIn: https://www.linkedin.com/in/roy-lee-swe/
  • Website: https://www.interviewcoder.co/

Where to Find David Phillips

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips/

In This Episode, We Cover

  • (00:00) Welcome and intro
  • (01:05) Roy's Harvard saga and forced gap year
  • (03:00) Learning to code in isolation
  • (05:10) Attending community college and meeting co-founders
  • (07:00) Transferring to Columbia and launching Interview Coder
  • (08:00) Building a viral-first product in 4 days
  • (10:20) The MVP, tech stack, and early traction
  • (12:00) Using the tool to land offers from Amazon, Meta, and more
  • (13:30) Turning open source into $10K MRR
  • (15:00) The infamous Amazon video and Columbia’s response
  • (17:30) Leveraging virality to fight institutional pressure
  • (19:30) Controversy and creator growth strategy
  • (20:40) Getting into Z Fellows and its impact
  • (22:00) Roy’s new startup: Pike
  • (23:30) What's next and where to follow along

Referenced

  • Interview Coder: https://www.interviewcoder.co
  • Z Fellows: https://zfellows.com
  • Roy’s Amazon interview post: Roy’s X Profile
  • LeetCode: https://leetcode.com
  • Cursor (AI code editor): https://www.cursor.sh
  • Claude (AI assistant by Anthropic): https://www.anthropic.com/index/claude


Show more...
7 months ago
24 minutes

Startup Growth Podcast
Three Startups, $70M Raised, and One Successful Exit

Jay Reno is the founder and CEO of PointHound, a free platform helping hundreds of thousands of people earn and redeem credit card points for maximum value—often unlocking free business class flights. But Jay’s journey started long before PointHound. He previously founded Feather, a furniture subscription startup that redefined how millennials furnish their homes. Under Jay’s leadership, Feather scaled to $15M in annual recurring revenue, raised over $70M in funding, and was ultimately acquired in 2022.

In this conversation, Jay and David dive deep into the full founder arc—from early failures to scaling a venture-backed operation—and everything he's applying to his new startup. They discuss:

  • How Jay lost his life savings on his first company—and what he learned
  • The origin story behind Feather and the cold email that changed his life
  • How Feather scaled from a duct-taped operation to $15M in ARR
  • The operational challenges of running a semi-vertical logistics business
  • Why the pandemic forced a complete shift in strategy
  • What it’s like raising capital when everything looks perfect—but still isn’t easy
  • How to build loyalty and change consumer behavior with time
  • Why most people are wasting their credit card points—and what to do instead
  • How PointHound helps anyone fly business class for free
  • The cards Jay wishes he used while running Feather
  • What Jay learned going through YC… twice
  • Much more

Brought to you by:

  • Fondo — Your all-in-one accounting platform for startups. Bookkeeping, taxes, and R&D credits, on autopilot. https://tryfondo.com
  • PointHound — Redeem credit card points for free flights. No guesswork, just travel. https://pointhound.com

Find the transcript at: Startup Growth Podcast

Where to Find Jay Reno

  • X: @jayjreno
  • LinkedIn: linkedin.com/in/jayjreno
  • Website: https://pointhound.com

Where to Find David Phillips

  • X: @davj
  • LinkedIn: linkedin.com/in/davjphillips

In This Episode, We Cover

  • (00:00) Introduction and welcome
  • (01:22) Jay’s first founder punch with his grocery delivery startup
  • (03:06) Early lessons from failure and jumping into Feather
  • (04:43) Starting Feather and how the West Elm deal happened
  • (06:55) Applying to YC from a pizza shop Wi-Fi
  • (08:59) Feather’s scrappy early operations—manual delivery and DIY logistics
  • (13:14) Raising a $3.5M seed and hitting 7% week-over-week growth
  • (19:46) Operating out of a chaotic Dumbo retail space
  • (22:34) Discovering a B2B growth channel and building a team
  • (26:48) The surprising difficulty of raising a Series A
  • (30:22) Closing a $30M warehouse line to unlock scale
  • (33:20) How COVID froze growth and forced strategy shifts
  • (36:02) Selling Feather to Vesta in 2022
  • (37:03) Jay’s time in VC and why he returned to building
  • (38:53) The pain of points mistakes and the birth of PointHound
  • (40:20) The best (and worst) credit cards for startups
  • (41:51) Making points redemption 10x easier and smarter
  • (43:40) Getting PointHound’s first users through Reddit and Bookface
  • (45:32) Final thoughts and where to find Jay

Referenced

  • Feather: https://feather.com
  • Y Combinator (YC): https://www.ycombinator.com
  • 645 Ventures: https://645ventures.com
  • Brex Card: https://www.brex.com/card
  • Amex Business Gold: https://www.americanexpress.com/en-us/business/credit-cards/business-gold-card
  • Capital One Spark Miles: https://www.capitalone.com/small-business/credit-cards/spark-miles
  • Bookface (YC network): https://bookface.ycombinator.com
  • Reddit r/Churning: https://www.reddit.com/r/churning/
Show more...
7 months ago
46 minutes

Startup Growth Podcast
He Bought a College to Fix Higher Ed — Tade Oyerinde’s $100M Vision

Tade Oyerinde is the founder and chancellor of Campus, a revolutionary online community college reimagining access to higher education. Starting with viral dorm-room startups, Tade’s journey took him from building UniRoulette and CampusWire to acquiring an accredited college and launching Campus. Today, Campus serves over 2,000 students, employs 240+ staff, and has raised $100M+ in venture capital, all while helping students graduate debt-free.

In this conversation, Tade shares the winding path to building Campus, including:

  • Building viral products from a college dorm
  • Pivoting away from unsustainable growth and recognizing false signals
  • Learning the limitations of synchronous social platforms
  • Discovering the adjunct professor pay gap—and turning it into a wedge
  • The insight that top professors teach at community colleges too
  • Why he acquired a college instead of starting one from scratch
  • Building custom education software from the ground up
  • Raising capital from Sam Altman, Jason Citron, and General Catalyst
  • Why Campus prioritizes human support over AI
  • Much more

🔑 Key Takeaways

  • Viral ≠ Valuable: Tade learned early that virality alone doesn’t lead to retention or sustainable business models.
  • Adjuncts are the secret weapon: Many top professors are adjuncts—underpaid and overlooked—yet open to better platforms.
  • Perception ≠ quality: Community colleges often offer courses from the same professors as elite schools, but carry social stigma.
  • Build infrastructure, not integrations: Campus runs fully on internally built tools for instruction, administration, and student support.
  • Debt-free college is viable: Through Pell Grants and optimized economics, 86% of Campus students pay $0 out-of-pocket.
  • Support at scale is human-powered: Every 50 students are supported by a real advisor, counselor, or coach—not AI.
  • Raising was milestone-driven: Capital was unlocked at each inflection point—acquisition, accreditation, first students, scaled cohorts.
  • Skepticism is a superpower: Having experienced the hype-crash cycle before, Tade built Campus with deliberate, durable conviction.

Brought to you by:

  • Fondo — The all-in-one accounting platform for startups: https://www.fondo.com

Where to Find Tade Oyerinde

  • LinkedIn: https://www.linkedin.com/in/tadeoyerinde
  • Website: https://www.campus.edu

Where to Find David Phillips (Host)

  • X: https://x.com/davj
  • LinkedIn: https://www.linkedin.com/in/davjphillips

In This Episode, We Cover

  • (00:00) Intro to Tade and the Campus vision
  • (01:35) The Tade origin story: homeschool, aerospace, and building UniRoulette
  • (03:45) Going viral and raising a seed round in London
  • (05:55) The retention issue with synchronous social apps
  • (07:15) Pivoting into mobile apps for universities
  • (09:35) Building CampusWire and avoiding enterprise sales
  • (11:05) Cold emailing 1M professors to grow
  • (12:45) How COVID created a head-fake spike
  • (14:20) Discovering the adjunct pay gap
  • (15:35) The insight that UCLA profs teach at community colleges too
  • (16:25) Why community college students weren’t retaining
  • (18:10) Walking away from CampusWire to start Campus
  • (19:45) Meeting Ralph Wolff, and the plan to buy a college
  • (21:10) How Tade raised to acquire an accredited school
  • (23:05) The challenge of buying a college as a dropout
  • (24:40) Getting the first students and launching Campus
  • (26:10) Making college free via Pell Grants
  • (27:40) The impact of improving retention on gross margins
  • (29:10) Building all the software from scratch
  • (30:10) Campus’ live class model and top professors
  • (31:05) Hiring a full-time human for every 50 students
  • (32:10) Lowering CAC from $15K to sustainable levels
  • (33:50) Unlocking funding across inflection points
  • (35:10) What’s next for Campus

Referenced
UniRoulette (inspired by ChatRoulette):
https://en.wikipedia.org/wiki/Chatroulette

The Social Network (Film):
https://www.imdb.com/title/tt1285016/

Clubhouse liquidity challenges:
https://www.nytimes.com/2021/07/11/style/clubhouse-app-decline.html

Andreessen Horowitz's investment in Clubhouse:
https://a16z.com/2021/01/24/investing-in-clubhouse/

CampusWire (Tade's previous startup):
https://www.campuswire.com/

General Catalyst:
https://www.generalcatalyst.com/

UC San Diego Transfer Admissions:
https://admissions.ucsd.edu/transfer/

FAFSA Application (for Pell Grants):
https://studentaid.gov/h/apply-for-aid/fafsa

Show more...
7 months ago
35 minutes

Startup Growth Podcast
Fondo is an all-in-one accounting platform for startups. Get your books closed, taxes filed, and cash back from the IRS.