Why Data Is the Next $1 Trillion Market
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Today's show:
How many startups matter in tech? Fewer than you think. That's why venture capitalists are tripping over themselves to get onto their cap tables, no matter the cost. Why? Footwork's Nikhil Basu Trivedi argues that the Valley has never been more "power-law-pilled" than it is today. Basu Trivedi joined Cendana Capital's Michael Kim and TWiST's Alex Wilhelm to go deep on secondary markets, the state of startup M&A, why the SaaSpocalypse may be temporary, and what could trigger a retrenchment of the AI trade. It's Wednesday, so it's time for our venture capital roundtable to go deep on how VCs are investing today, and where on the horizon they have their eyes fixed!
Guest links:
Nikhil Basu Trivedi https://x.com/nbt
Footwork https://www.footwork.vc/
Michael Kim https://x.com/MKRocks
Cendana Capital https://www.cendanacapital.com/
Show links:
The USVC-Anduril blowup https://x.com/ankurnagpal/status/2072701195714531398
Kline Hill Cendana Partners https://www.secondariesinvestor.com/kline-hill-and-cendana-raise-400m-for-second-vc-secondaries-fund/
GPTZero's exit https://gptzero.me/news/preserving-whats-human/
Salesforce buys Fin https://www.salesforce.com/news/press-releases/2026/06/15/salesforce-signs-definitive-agreement-to-acquire-fin/
Vercel buys Better Auth https://vercel.com/blog/vercel-acquires-better-auth
Figma buys Bud https://techcrunch.com/2026/07/07/figma-acquires-team-behind-a-vibe-coding-app/
Protoge https://withprotege.ai/
Windborne https://windbornesystems.com/
Etched https://www.etched.com/
Lovable's reported raise https://sifted.eu/articles/lovable-300m-13-2bn-valuation
Josh Browder https://x.com/Joshuabrowder
Timestamps:
0:00 Introduction: Nikhil Basu Trivedi (Footwork) & Michael Kim (Cendana Capital)
1:59 The Anduril vs. USVC secondary market blowup
4:08 Why Silicon Valley is 'power-law-pilled'
8:23 Plaud: If your work depends on conversations — interviews, meetings, calls — you need a Plaud NotePin. You can check it out at https://Plaud.ai/twist and use code TWIST for 10% off!
9:37 Information asymmetry in the secondary markets
9:45 Every.io — For all of your incorporation, banking, payroll, benefits, accounting, taxes or other back-office administration needs, visit https://every.io
15:02 Is SPV fraud smoke or fire?
16:32 Superhuman acquires GPTZero
19:54 Agree.com - Stop chasing invoices and automate your entire contract-to-cash stack. Go to https://agree.com and tell them Jason sent you to get 50% off for life!
21:10 The M&A wave
27:19 The SaaSpocalypse debate
29:59 DigitalOcean - Head to https://do.co/twist to start building on DigitalOcean's AI-Native Cloud today — and cut your AI workload costs by up to 50%.
30:44 Data's moment in the energy → compute → data loop
35:01 Where will AI value accrue?
40:04 What could cause an AI correction?
42:17 Why some companies are "too big to miss"
46:23 China's possible open-weight model ban
53:28 Young founders: Etched, Thiel Fellows, Z Fellows, Neo
55:33 Portfolio spotlight: WindBorne's weather balloons and data moat
58:47 Michael's favorite fund manager: Josh Browder
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Footwork’s Secret Sauce | Mike Smith and Nikhil Basu Trivedi
Nikhil Basu Trivedi and Mike Smith are the Co-founders of Footwork where they invest up to $15 million in Seed and Series A rounds. This is the first time they've ever sat down to record a conversation together on video.
We talk about starting the firm in 2020, their secret sauce for working with founders, lessons investing in Canva’s Seed round, scaling Stitch Fix from $0 to $1B revenue in five years with $17m in capital, why AI will enable a new wave of entrepreneurship, and how public company boards are discussing AI today.
Thank you to Tony Staehelin, Andrew Riesen, and Hunter Walk for helping brainstorming topics for the conversation.
Thank you to Flex for supporting this episode.
Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz
Timestamps:
(0:24) Starting Footwork from a tweet in 2021
(3:11) Difference between startup and public company boards
(4:52) 20-40% of board meetings are now about AI
(7:48) How Footwork’s investing in AI today
(10:37) AI will enable millions of new entrepreneurs
(15:04) 37 questions to ask when starting a VC firm
(17:40) Importance of differences
(23:08) The pace of VC is faster than operating
(26:26) Footwork’s secret sauce (2x board seats, 1-pager)
(31:59) Investors should talk to and help employees
(37:05) Building an equal-carry partnership
(39:33) How Footwork makes decisions
(43:21) Navigating short-termism and politics in VC firms
(51:18) “You’re only as good as your next investment”
(53:30) Characteristics of great founders
(58:13) Canva’s Seed pitch in 2014
(1:02:54) Joining Stitch Fix as 4th employee
(1:06:40) Scaling Stitch Fix $0 to $1B revenue in five years with $17m in capital
(1:16:48) Raising from Bill Gurley after a failed Series A
(1:19:40) Footwork’s office near YC
(1:22:10) Opportunities in consumer health
(1:25:20) Using flash mobs to win deals
(1:26:15) Dad life
Referenced
Footwork: https://www.footwork.vc/
Anything: https://www.anything.com/
Table22: https://www.table22.com/
Canva: https://www.canva.com/
Stitch Fix: https://www.stitchfix.com/
Honeydew: https://www.honeydew.com/
Follow Mike
Twitter: https://x.com/msmith492
LinkedIn: https://www.linkedin.com/in/michaelcsmith1
Follow Nikhil
Twitter: https://x.com/nbt
LinkedIn: https://www.linkedin.com/in/nikhilbt
Substack: https://nbt.substack.com/
Follow Turner
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak
Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/
SaaStr 705: Decoding the 2024 Market: How to Scale from Go-to-Market Through IPO for the Year Ahead with ICONIQ Growth's General Partner Doug Pepper and Head of Analytics, Christine Edmonds
A holistic and well-executed go-to-market strategy is one of the key pillars that drives sustainable, long-term growth for software companies. But there is a dearth of data that leaders can leverage to inform building out the best team, strategies, and tactics to scale their go-to-market organization.
Leveraging proprietary data from over 200 leading GTM executives and tens of thousands of data points related to executive profiles across Sales and Marketing leaders, Doug Pepper, General Partner, and Christine Edmonds, General Partner and Head of Analytics at ICONIQ Growth will share detailed answers to the key go-to-market questions from B2B SaaS leaders including:
The latest insights on what "effective" scaling means in today's environment
Best practices for building out GTM teams and processes
Learnings related to what profiles make the most successful IPO-ready executive hires
How top companies are tweaking tactics in today's environment to drive efficient selling
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SaaStr hosts the largest SaaS community events on the planet.
Join us in 2024 at:
SaaStr Annual: Sept. 10-12 in the SF Bay Area. Join 12,500 SaaS professionals, CEOs, revenue leaders and investors for the world's LARGEST SaaS community event of the year. Podcast listeners can grab a discount on tickets here: https://www.saastrannual2024.com/buy-tickets?promo=fave50
SaaStr Europa: June 5-6 in London. We'll be hosting the 5th SaaStr Europa in London for two days of content and networking. Join 3,000 SaaS and Cloud leaders. Podcast listeners can grab a discount on Europa tickets here: https://www.saastreuropa2024.com/buy-tickets?promo=fave20
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20VC: Why Small Funds Outperform Large Funds & AUM is a Vanity Metric | Why 99% of Investments in AI Startups Will Go To Zero | Being a "Traction First" VC & Investing Lessons from Investing in Canva and Missing Figma with Nikhil Basu-Trivedi
Nikhil Basu Trivedi is Co-Founder & General Partner at Footwork, an early-stage focused venture firm investing its first fund. In his venture career, he has invested in the early rounds of several companies that have exited or are currently valued at over $1B, including Athelas, Canva, ClassDojo, Color Health, Frame.io, Imperfect Foods, Lattice, and The Farmer's Dog. Prior to Footwork, Nikhil was a Managing Director at Shasta Ventures, on the investment team at Insight Partners, and on the founding team at Artsy.
In Today's Episode with Nikhil Basu Trivedi We Discuss:
1. From Summer Intern to Founding a Firm: The 13 Year Journey:
How did Nikhil first make his way into venture as an intern at Insight Partners in NYC?
What does Nikhil know now that he wishes he had known on his first day in venture?
Why does Nikhil advise all young VCs to "not look at their business card"? Why does title not matter in venture?
Should founders meet with Juniors as well as GPs and more senior people?
2. Small Funds Outperform Large Funds:
Why does Nikhil believe that small funds outperform large funds?
Why is AUM the biggest bullshit metric in VC?
How does Nikhil advise seed stage founders who have offers from seed firms for smaller rounds at lower valuations and are weighing them against larger rounds with higher valuations from multi-stage funds?
Does Nikhil believe that platform value-added services really provide any value?
3. The Art of Investing:
What has been Nikhil's biggest investing win? How has it changed his approach to investing?
How does Nikhil prioritize between people, traction, and market? What is most important?
What has been Nikhil's biggest investing miss? How has that changed his approach?
Does Nikhil believe the great founders are immediately obvious?
Why is market size the single question that keeps Nikhil up the most?
4. The Dysfunctions of Venture Capital:
What are the single biggest areas of misalignment between GP and LP?
What do many GPs see and know well that LPs should know and see more of?
What are the biggest ways that decision-making breaks down in a venture fund?
Why does Nikhil believe that so much of the investment in AI is going to go up in flames?
SaaStr 637: Unveiling the Data Behind Effective Scaling with ICONIQ Growth General Partner Doug Pepper and ICONIQ Growth Partner & Head of Analytics Christine Edmonds
In this illuminating session, ICONIQ Growth general partner Doug Pepper and head of analytics Christine Edmonds will share some of the latest insights from ICONIQ's annual "Growth and Efficiency Study" which utilizes aggregated operating data from a large set of enterprise SaaS companies, about half of which have gone on to IPO and/or been named to the Cloud 100 list. From the metrics most indicative of healthy business fundamentals and what top quartile performance looks like across these KPIs, to how those core metrics may be impacted in the current environment and where leaders are focusing in response to the macroeconomic uncertainty of today, Doug and Christine will share what strength looks like at all stages of company growth.
Updated slides: https://www.slideshare.net/saastr/unveiling-the-data-behind-effective-scaling-with-iconiq-growth-253098692
Video: https://youtube.com/live/oRtla9psS_8
Want to join the SaaStr community? We're the 🌎largest community for B2B software.
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SaaStr 615: Where Venture Capital Really is Right Now, With Accel, Iconiq Growth, and Salesforce Ventures at G2 Reach
SaaStr CEO Jason Lemkin recently moderated a session with 3 of the best investing in SaaS: Doug Pepper, GP at Iconiq, Arun Mathew, GP at Accel, and Alex Kayyal, VP and head of all of Salesforce Ventures. The four deep-dive on the real state of venture capital today and into 2023.
This podcast was recorded live during G2's digital reach event. Check out the rest of the sessions over at Reach.G2.com
This episode is an excerpt from the session. Watch the full video: https://youtu.be/hTvNqr395nY
Want to join the SaaStr community? We're the 🌎largest community for B2B software.
Subscribe for weekly updates: https://www.saastr.com/subscribeform
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SaaStr 557: Where Venture Is Right Now with Iconiq GP Doug Pepper and SaaStr Founder Jason Lemkin
Doug's been an investor is so many of top SaaS companies, from Marketo to Calendly to Loom to Braze to Lattice. Today he's a general partner at one of the top growth-stage VC firms, Iconiq. He and Jason do a deep dive on where the venture markets really are today, and what it means for founders.
Key Takeaways:
#1. VC remains open — at least for deals
#2. So many top, mid, and later-stage SaaS companies raised tons of capital in 2021, so much … that few really need to go back to market and raise again this year.
#3. VCs are taking more time, but more "back to normal" time Growth deals can still be done in 3-4 weeks, just not 1 week now.
#4. Not only is there is plenty of money in venture — but even more is coming. Top funds are continuing to raise huge funds.
#5. The biggest issue in venture today is just that founders haven't changed their expectations
#6. 2016 was tough, too.
#7. Watch What the Big PE Firms like Vista, Thoma Bravo, etc. do in SaaS. They know.
Full video: https://youtu.be/WehTJ4RNBaQ
Want to join the SaaStr community? We're the 🌎largest community for B2B software.
Subscribe for weekly updates: https://www.saastr.com/subscribeform
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SaaStr 322: ICONIQ Capital General Partner Doug Pepper on Key Lessons from a $5B SaaS Category Leader
Many people make the false assumption that the path for a highly successful SaaS company is straight "up and to the right". Of course, for those involved, the reality of the journey is characterized by a series of obstacles that must be navigated. Fmr. Shasta Ventures Doug Pepper will share the key challenges that were overcome to allow Marketo to become a $5B SaaS Category Leader in Marketing Automation.
This podcast is an excerpt from Doug's session at SaaStr Europa. You can find the full video and transcript on our blog.
SaaStr 178: 10 Key Lessons From Scaling Marketo to IPO with Phil Fernandez, Former Marketo CEO & Venture Partner @ Shasta Ventures
Phil Fernandez is a Silicon Valley veteran, with more than 35 years of experience building and leading breakout technology companies. Phil co-founded Marketo in 2006 and led the company as Chairman and CEO for a decade, overseeing its successful IPO and acquisition by Vista Equity Partners. Prior to Marketo, Phil served as president and COO of Epiphany, an enterprise customer relationship management (CRM) software company. Today, Phil is a Venture Partner with Shasta Ventures, the fund with a portfolio including the likes of Nest, eero, Zuora, Canva and many more incredible companies.
In Today's Episode You Will Learn:
When is the right time to hire your first CRO? Where did Phil make a big mistake in who owns what revenue numbers? What are the traits that make the best CROs? How should they look to work with both sales and marketing to drive efficiency internally?
Why does Phil believe you must hire the most senior Chief People Officer as soon as you can? What does the role of "Chief People Officer" really embody? How should they look to work with HR internally? Who should they report to? How does this role change with a scaling organisation?
How has Phil seen the relationship between average contract value and potential for expansion change? What is the correlation between and ongoing services component and both customer NPS and expansion? Where did Phil go wrong with this at Marketo?
How should emerging SaaS startups today be thinking about technical legacy debt? Why does Phil believe it is never to early to have a Head of Research function? How should this function work with the team to build the latest technology into new products?
Why did Steve sell Marketo to Vista Equity Partners? What was the thesis and big learnings from that experience? What does Phil mean when he says he did not "watch the clock properly''? How can founders today be proactively thinking about ramp time for sales reps, new product engagement etc.
Read the full transcript on our blog.
If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
SaaStr
Phil Fernandez
20VC: Why It Is BS That You Never Regret Paying A High Price To Get Into A Good Company, Why There Are Only 2 Price Points That Work in SaaS and Why eSports Will Be Bigger Than Traditional Sports in 5 Years Time with Jason Pressman @ Shasta Ventures
Jason Pressman is a Managing Director @ Shasta Ventures who have made investments in the likes of Nest, Dollar Shave Club, Smule, Class Dojo and more. With 10 portfolio company investments under his belt, Jason invests in both enterprise and consumer, currently serving on the boards of Crittercism, subscription billing unicorn Zuora, as well as Nextdoor and mobile music platform Smule. Prior to joining Shasta, Jason was Vice President, Strategy and Operations at venture-backed Walmart.com, where he took the online retailer from zero to large scale revenue in five years.
In Today's Episode You Will Learn:
1.) How Jason made his way into the world of venture from Walmart? What were the big takeaways from seeing Walmart enter their hyper-growth phase?
2.) Why does Jason believe it is bullshit to say, "you never regret paying a high price for getting into a good company"? How does Jason evaluate entry point? What makes one entry point attractive and another not?
3.) What does Jason see as the catalysts for the opening of public markets to tech companies? How long does he think this will continue? Is he concerned by the likes of Yext, IPOing with less than aggressive growth rates?
4.) Why does Jason believe there are only 2 price points that work in SaaS? What are they? How does this affect the structure and operations of your SaaS startup? What are the circumstances in which these price points do not apply?
5.) Why does Jason believe that eSports will be bigger than the NBA in 5 years? What are the catalysts driving this change? What needs to be formulated within eSports for this to happen?
Items Mentioned In Today's Show:
Jason's Fave Book: First, Break All The Rules
Jason's Most Recent Investment: Plays.tv
As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
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20VC: Mythbuster: Is Mobile Dying? Is AR/VR Overhyped? Is The Excitement Around Bots Justified with Sean Flynn, Partner @ Shasta Ventures
Sean Flynn is a Managing Partner @ Shasta Ventures where he invests in mobile-enabled consumer Internet and enterprise software companies. Sean has led Shasta's investments in Dollar Shave Club, Whisper and serves on the board of directors for the likes of TimeHop, Zefr, Swipely, Bloc and TigerText. Before joining Shasta, Sean worked at Yahoo, where he focused on growing the company's communication and messaging products such as Yahoo! Mail, Messenger, Groups and Flickr.
In Today's Episode You Will Learn:
1.) How Sean made his way into VC from the titan that is Yahoo?
Now today I want to do something slightly different and do a myth busting episode, take a couple of sectors and discuss whether they are truths and complexities to the core statement.
2.) Starting with the most common assumption in VC that it is all about team, to what extent does Sean place team ahead of product and is this a slight misconception?
3.) Many are saying mobile is a dying space. Sean previously said, 'it is not dead yet'. Why is there promise for mobile? What will be the catalyst of it's death? How does this affect Sean's investment decision making?
4.) Another much hyped topic is AR/VR, is the excitement surround AR and VR justified? Where does Sean stand on investing in the installation phase of cycles?
5.) Similar to AR/VR is the hype surround bots justified? What will be the sustainable business model for bots?
Items Mentioned In Today's Show:
Sean's Fave Book: What Do You Do With An Idea
Sean's Fave Blog or Newsletter: Nuzzel, 538 Blog
Sean's Most Recent Investment: Tally
As always you can follow The Twenty Minute VC, Harry and Sean on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Snapchat here! This episode was brought to you by DesignCrowd, the online marketplace for custom graphic, logo and web design that helps startups, entrepreneurs, web developers and agencies outsource design projects to designers from around the world. How Does It Work? Once you have launched your brief, designers will begin submitting quality designs for you to review. With some constructive feedback, you can quickly generate a large gallery of designs that really do fit your needs. You can have exactly what you need within just three days. Once you have selected your favourite design, you will be sent all the files you require to update your branding. If you don't like any of the submitted designs, then DesignCrowd offers a money back guarantee. So checkout designcrowd.com/VC and enter the promo code VC100 to get an astonishing $100 off your next project.
20VC: The Future For Autonomous Vehicles & How Software Is Eating Cars with Nikhil Basu Trivedi, Investor @ Shasta Ventures
Nikhil Basu Trivedi is an early stage investor with Shasta Ventures, where he focuses on consumer, mobile and SaaS. Prior to joining Shasta, Nikhil was a member of the Insight Venture Partners team in NYC. Before making the move into venture, Nikhil co-founded Artsy in his sophomore year at Princeton University, Artsy now employs over 100 people and has raised over $50m in venture financing. One of Nikhil's main passions is self driving cars and so today's show will be centred around the proliferation of autonomous vehicles and what that means for us as a society?
In Today's Episode You Will Learn: 1.) How did Nikhil come to be a VC in SF having spent his early years in the UK?
2.) Why is Nikhil so excited about self-driving cars? What is the enabler that is allowing this mass rise of the autonomous vehicle?
3.) What happens in a world of little mechanical engineering at all, where repairs can be achieved with software updates? How does this change the complexity of production? How does this change what the supply chain might look like? How does this change the capital structure required?
4.)How does the rise of the autonomous vehicles effect the sharing economy? Is Nikhil bullish on Lyft, Uber, Didi? With on demand, when will we reach a point of equilibrium when the supply of drivers that gets drawn in and the price that attracts consumers will be equivalent?
5.) Who is the leader, is this a winner take all, will the acquisition of GM and Cruise mean a dominance? Who has Nikhil been impressed by?
Items Mentioned In Today's Episode:
Nikhil's Fave Book: Leading by Sir Alex Ferguson and Michael Moritz
Nikhil's Fave Blog: Mattermark Daily, CB Insights
Nikhil's Most Recent Investment: Tally
As always you can follow The Twenty Minute VC, Harry and Nikhil on Twitter here! If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here! The Twenty Minute VC is brought to you by Leesa, the Warby Parker or TOMS shoes of the mattress industry. Lees have done away with the terrible mattress showroom buying experience by creating a luxury premium foam mattress that is order completely online and ships for free to your doorstep. The 10 inch mattress comes in all sizes and is engineered with 3 unique foam layers for a universal, adaptive feel, including 2 inches of memory foam and 2 inches of a really cool latex foam called Avena, design to keep you cool. All Leesa mattresses are 100% US or UK made and for every 10 mattresses they sell, they donate one to a shelter. Go to Leesa.com/VC and enter the promo code VC75 to get $75 off!
Saastr 007: What It Takes To Get Series A Investor Interested and Guidelines To Manage Your Burn Rate with Doug Pepper, Partner @ Shasta Ventures
I am thrilled to welcome, Doug Pepper, Partner @ Shasta Ventures to the show today. Doug is a master when it comes to SaaS investments with his companies generating over $500m in revenue in 2015, having funded the likes of Marketo, Optimizely and Flurry. In today's show with Doug we discuss:
How Doug made his approach into investing?
What metrics are required for startups to get Series A investors interested?
What are the guidelines for a startup to manage their burn rate?
In future tough markets, we will see greater consolidation?
How can startups stand out when selling to CIO, CEO's and VPs?
In a round we call the 60 Second Saastr, we also hear:
What has been the scariest moment of Doug's VC career?
Why Doug is so excited for the future of mobile SaaS?
What the main effects are of the rise of bottoms up sales strategies?
If you would like to find out more about the show and the guests presented you can follow us on Twitter here:
Jason Lemkin
Harry Stebbings
Saastr
Doug Pepper
Product Hunt Radio: Episode 2 w/ Kat Manalac, Nikhil Basu Trivedi, & Jack Altman
This week Kat Manalac (Partner at Y Combinator), Nikhil Basu Trivedi (VC at Shasta Ventures), and Jack Altman (Growth at Teespring) join me (Ryan Hoover) in the second episode of PHR. We chat about online-to-offline apps, a product to fight those darn San Francisco parking tickets, and the trend toward anonymous communication. Products mentioned: Flock - http://www.producthunt.co/posts/flock Jukely - http://www.producthunt.co/posts/jukely design+code - http://www.producthunt.co/posts/design-code Cloak - http://www.producthunt.co/posts/cloak-ios Fixed - http://www.producthunt.co/posts/fixed Patreon - http://www.producthunt.co/posts/patreon Secret - http://www.producthunt.co/posts/secret Rando - http://www.producthunt.co/posts/rando Facebook Nearby Friends - http://www.producthunt.co/posts/fb-nearby-friends Intro/outro music by eldienneproductions -https://soundcloud.com/eldienneproductions/hip-hop-beat-instrumental --- Product Hunt is a daily leaderboard of brand new products. Visit producthunt.co.