49 episodes

Exploring the world’s greatest startup stories.

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.

The Peel with Turner Novak Turner Novak

    • Technology

Exploring the world’s greatest startup stories.

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.

    Building boldstart ventures from $1M to $850M with Ed Sim

    Building boldstart ventures from $1M to $850M with Ed Sim

    Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel

    Ed Sim is the Founder of boldstart ventures, which partners with bold founders reinventing the enterprise stack at the inception stage. Ed takes us inside the journey building boldstart, from its first $1m fund in 2010 up to $850m in AUM today.

    Timestamps:
    (00:00) Intro
    (03:48) Evolution of early stage investing(05:11) Inception stage investing
    (10:32) Backing bold founders reinventing the enterprise stack(11:20) Repeatable ways to build enterprise businesses
    (12:04) The 5 P’s of early stage investing
    (14:12) Backing Guy Podjarny and Snyk
    (18:18) Knowing when to follow-on
    (19:18) The 3 Ch's of a good board member
    (22:01) How Ed’s board role changes over time
    (24:20) Balancing founder friendly with returns
    (27:20) How to build customer relationships
    (30:24) Advice for closing customers
    (33:47) Creating the Seed category in 2009/10
    (37:31) boldstart’s $1m Fund 1
    (39:00) Why Ed didn’t join a large firm in 2012
    (39:55) boldstart’s $16.5m Fund 2
    (40:26) Why LPs passed on the first funds
    (43:11) Leading rounds in Kustomer, Snyk, BigID, and Blockdaemon in Fund 3
    (47:09) Why $112m Fund 4 was the hardest to raise(50:52) Ed’s approach to LP fundraising
    (55:12) Inside Meta’s acquisition of Kustomer and sale back to the founders
    (59:52) Backing Rahul from Superhuman a 2nd time
    (01:00:52) The different GTM playbooks
    (01:02:20) Importance of contract size and time to close
    (01:05:07) Why AI makes security more important
    (01:06:11) When to switch from founder-led sales(01:07:46) Backing ProtectAI after a conference
    (01:08:28) Balancing between inbound and outbound sales
    (01:09:55) Winners and losers in AI
    (01:15:26) Building the boldstart team
    (01:19:33) Lessons being an interim CEO
    (01:22:18) How ZIRP pulled revenue forward
    (01:29:08) The death of high growth software
    (01:32:58) Identifying startup opportunities incumbents won’t crush
    (01:35:00) Second order effects of AI
    (01:36:46) Using "Intuitive TAM" to size new markets
    (01:38:04) Investing before there’s a market map
    (01:38:57) Balancing family, fitness, and career



    Referenced:

    https://boldstart.vc/

    Turning Down HBS: https://x.com/edsim/status/1315644287007240193

    Ed’s tweet on raising Fund 4: https://x.com/edsim/status/1315644287007240193

    Second Order Effects of AI: https://www.whatshotit.vc/p/whats-in-enterprise-itvc-379

    Death of Hyper Growth: https://x.com/edsim/status/1797613384994623808



    Where to find Ed:

    Twitter: https://twitter.com/edsim

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

    Newsletter: https://www.whatshotit.vc/



    Where to find Turner:

    Twitter: https://twitter.com/TurnerNovak

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

    Newsletter: https://www.thespl.it/

    • 1 hr 45 min
    Scaling Instacart to $10+ Billion with ex-President Nilam Ganenthiran

    Scaling Instacart to $10+ Billion with ex-President Nilam Ganenthiran

    Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel

    Nilam Ganenthiran is the founder and CEO of Beacon Software. Previously, he was the 12th employee and President at Instacart.

    We talk tactics for customer research, building customer relationships, balancing strategy and execution, how to serve on and manage a board, what happened when Amazon bought Instacart’s biggest customer Whole Foods, inside its COVID response, surviving eight months of runway in 2015, his new company Beacon Software, and more.

    Timestamps:

    (00:00) Intro
    (04:23) Inside Amazon acquiring Instacart’s biggest customer, Whole Foods
    (12:13) Lessons from quickly signing 8 of the top 10 grocers
    (13:06) Why grocers were slow to adopt ecommerce
    (15:29) Building “Shopify for grocers”
    (16:22) Sales = building relationships
    (19:05) Why Wegman’s is one of the best grocers in the world
    (20:43) Cold calling Wegman’s and signing them two years later
    (24:33) How to do customer research
    (26:59) Catching an Uber in suits on the highway
    (28:50) Why Instacart was possible back in 2013
    (30:36) Launching Instacart’s advertising network
    (38:46) Growing 5x in 5 weeks during COVID
    (45:20) How Nilam started angel investing
    (47:56) Advice for sitting on boards
    (50:00) The roles and incentives of a board member
    (54:03) Deciding when to keep going and when to give up
    (56:02) Nilam’s framework around optionality
    (59:17) Seven years of weekly redeye flights
    (1:00:30) Almost running out of money 8 months after Instacart’s Series C
    (1:07:54) Why time is your scarcest resource & startups are default dead
    (1:10:00) Nilam’s new company, Beacon Software
    (1:11:28) Why he’s excited about AI
    (1:13:25) How AI makes human relationships more important
    (1:14:41) Turner’s investing lessons from family members

    Beacon Software: https://beaconsoftware.ca/

    Where to find Nilam:

    Twitter: https://twitter.com/nilamg

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

    Where to find Turner:

    Twitter: https://twitter.com/TurnerNovak

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

    Newsletter: https://www.thespl.it/

    • 1 hr 16 min
    How the Smartest Companies Use AI | Ankur Goyal, Braintrust

    How the Smartest Companies Use AI | Ankur Goyal, Braintrust

    Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel

    Ankur Goyal is the Founder and CEO of Braintrust, the end to end developer platform for building the world's best AI products. Their customers include companies like Instacart, Zapier, Notion, Airtable, Replit, and more.

    We hit on the importance of LLM evals, advice for building AI products, why the best companies have two AI product roadmaps, and his non-conventional advice for founders.

    Timestamps:

    (00:00) Intro
    (04:04) Why everyone’s now an AI company
    (06:03) Reasons LLM evals are so important
    (08:10) Typescript becoming the language of AI
    (09:19) Replacing vibe checks with Braintrust
    (10:37) Making OpenAI’s protocols the standard
    (11:27) Why the best companies have two AI roadmaps
    (13:06) Building your product so each LLM release makes it better
    (14:54) Predicting AGI is impossible
    (15:54) Why people who work with LLMs aren’t worried about AI safety
    (16:52) The best developers are all-in on co-pilots
    (18:11) How AI is changing software development
    (21:09) Combining IDE, CIDC, and observability in one product
    (27:18) Are models more like CPU’s or relational databases?
    (30:14) How to pick an LLM
    (33:00) Advice for staying on top of new AI developments
    (34:30) Why tool calling is so important
    (38:02) Advice for young software engineers
    (40:25) Learning to code doing linear algebra homework
    (42:36) Lack of purpose interning in big tech
    (44:07) Working at MemSQL learning to be a founder
    (47:52) How to get a job at a startup
    (50:43) Building his first startups product on an international flight
    (52:39) Three lessons from his first failed startup
    (54:46) Don’t delegate what you’re good at
    (55:46) Why you should be careful listening to VCs advice
    (57:34) Tactics for successful delegation
    (59:36) Why Ankur doesn’t do any meetings
    (01:02:42) The importance of self-service in unlocking certain customer segments
    (01:05:14) How Braintrust got started
    (01:07:45) Advice on picking your target customers
    (01:10:35) How Braintrust hires with work trials
    (01:15:21) Balancing security with a modern UI
    (01:17:49) Why it’s hard to sell non-AI products right now
    (01:19:21) Advice for selling to large enterprises
    (01:23:10) Ankur’s favorite AI products

    Referenced:

    https://www.braintrustdata.com/

    SICP Book

    PDF: https://web.mit.edu/6.001/6.037/sicp.pdf

    Hardcopy: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871

    Linear’s guide to work trials: https://linear.app/blog/why-and-how-we-do-work-trials-at-linear

    Where to find Ankur:

    Twitter: https://twitter.com/ankrgyl

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

    Where to find Turner:

    Twitter: https://twitter.com/TurnerNovak

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

    Newsletter: https://www.thespl.it/

    • 1 hr 27 min
    Lessons From 21 Years of VC Fund Investing | Alan Feld, Vintage Investment Partners

    Lessons From 21 Years of VC Fund Investing | Alan Feld, Vintage Investment Partners

    Get Attio, the next generation of CRM: https://bit.ly/AttioThePeelAlan

    Feld is the Founder and Managing Partner of Vintage Investment Partners. Vintage is one of the largest fund of funds in the world, managing over $4 billion across what is mostly investments into other venture funds, plus some secondary and direct startup investments at the growth stage.

    Timestamps:

    00:00 Intro
    03:53 What is Vintage
    05:40 Why VCs adding value can waste a founder’s time
    09:01 VC, where the asset chooses the investor
    10:14 Fund size is the enemy of returns in VC
    14:57 What people get wrong about FoFs
    16:01 The value FoFs bring to LPs
    17:11 Why entrepreneurs drive VC returns
    17:55 Vintage’s unique FoF model
    19:05 Does replacing the founders with an outside CEO work?
    21:39 Starting Vintage after the Dot Com Crash in 2002
    23:41 Buying secondaries at 70-80% discounts
    25:13 Biggest mistakes when buying secondaries
    26:18 Research around what makes the best entrepreneurs
    31:09 Lessons from six downturns
    34:41 Comparisons between 2002 and 2022
    37:07 Advice for raising your first VC fund
    41:16 The importance of differentiation
    45:57 Sustainable ways to differentiate
    49:05 What Vintage looks for in new fund investments
    49:57 Advice for scaling a VC firm
    53:47 Succession planning
    57:50 What Alan’s doing post-Vintage

    Vintage Investment Partners: https://www.vintage-ip.com/

    Where to find Alan:

    Twitter: https://twitter.com/alanf_feld

    LinkedIn: https://www.linkedin.com/in/alan-feld-1744389/

    Where to find Turner:

    Twitter: https://twitter.com/TurnerNovak

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

    Newsletter: https://www.thespl.it/

    • 1 hr 3 min
    Fixing The Maternal Health Crisis with Anu Sharma at Millie

    Fixing The Maternal Health Crisis with Anu Sharma at Millie

    Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel

    Anu Sharma is the Co-founder and CEO of Millie, building a better care system from the inside out. Our conversation covers the existing maternal health system, how Millie is reinventing it, and how to succeed building a healthcare company.

    Timestamps:
    (00:00) Intro
    (03:16) Problems in US maternity care
    (13:21) Why insurance reimbursement drives healthcare
    (16:11) How bundled care unlocks personalization
    (18:48) From fiction writer to 20 years in healthcare
    (24:22) Why consumers don’t act like consumers in healthcare
    (26:09) The reason scale matters
    (27:43) Bundled payments and new care design
    (32:16) What make Millie unique
    (35:58) Importance of picking regional markets in healthcare
    (37:08) The two paths for insurance reimbursement
    (41:08) Why distribution is the product in healthcare
    (44:25) Opportunities in cash pay care
    (48:28) How Anu fundraised without a product
    (51:06) The future of in-person, hybrid, and virtual healthcare
    (52:56) Building maternity clinics for $150k

    Check out Millie: https://www.millieclinic.com/

    Where to find Anu:
    Twitter: https://twitter.com/anu_anusharma1
    LinkedIn: https://www.linkedin.com/in/anu-sharma-b169b12

    Where to find Turner:
    Twitter: https://twitter.com/TurnerNovak
    LinkedIn: https://www.linkedin.com/in/turnernovak/
    Newsletter: https://www.thespl.it/

    • 58 min
    Aaron Levie | The $1 Trillion AI Opportunity, Stories From Early Days of Box

    Aaron Levie | The $1 Trillion AI Opportunity, Stories From Early Days of Box

    Get Attio, the next generation of CRM: https://bit.ly/AttioThePeel

    Aaron Levie is a co-founder and the CEO of Box. This conversation covers opportunities in AI, the early days of Box, and lessons Aaron's learned on his founder journey.

    Timestamps
    (00:00) Intro
    (03:11) Why ChatGPT was an iPhone moment
    (04:37) Advice for large companies incorporating AI
    (11:16) Why AI will add jobs, not steal them
    (16:13) How AI is supercharging Box’s products
    (19:03) AI agents: the $1 trillion opportunity
    (25:27)Estimating size of new markets(29:58) Starting Box with high school friends
    (33:18) Living out of their first office
    (34:52) Why early investors passed on Box
    (37:24) Pivoting from consumer to B2B
    (39:53) How Box got its first customers
    (41:57) Should founders talk to Associates at VC firms?
    (43:26) How Mamoon at Kleiner saved Box at its Series B
    (46:25) Turning down an acquisition before IPO
    (50:51) Why Box’s IPO was so hard
    (54:11) Fending off an activist investor during COVID

    Check out Box: https://www.box.com/

    Where to find Aaron:

    Twitter: https://twitter.com/levie

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

    Where to find Turner:

    Twitter: https://twitter.com/TurnerNovak

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

    Newsletter: https://www.thespl.it/

    • 58 min

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