The Peel with Turner Novak Turner Novak

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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
(01:25:19) Lessons being an interim CEO
(01:27:15) 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/

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/

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/

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/

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/

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/