The state of VC within software and AI startups – with Peter Walker
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In this episode of The Pragmatic Engineer, I sit down with Peter Walker, Head of Insights at Carta, to break down how venture capital and startups themselves are changing.
We go deep on the numbers: why fewer companies are getting funded despite record VC investment levels, how hiring has shifted dramatically since 2021, and why solo founders are on the rise even though most VCs still prefer teams. We also unpack the growing emphasis on ARR per FTE, what actually happens in bridge and down rounds, and why the time between fundraising rounds has stretched far beyond the old 18-month cycle.
We cover what all this means for engineers: what to ask before joining a startup, how to interpret valuation trends, and what kind of advisor roles startups are actually looking for.
If you work at a startup, are considering joining one, or just want a clearer picture of how venture-backed companies operate today, this episode is for you.
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Timestamps
(00:00) Intro
(01:21) How venture capital works and the goal of VC-backed startups
(03:10) Venture vs. non-venture backed businesses
(05:59) Why venture-backed companies prioritize growth over profitability
(09:46) A look at the current health of venture capital
(13:19) The hiring slowdown at startups
(16:00) ARR per FTE: The new metric VCs care about
(21:50) Priced seed rounds vs. SAFEs
(24:48) Why some founders are incentivized to raise at high valuations
(29:31) What a bridge round is and why they can signal trouble
(33:15) Down rounds and how optics can make or break startups
(36:47) Why working at startups offers more ownership and learning
(37:47) What the data shows about raising money in the summer
(41:45) The length of time it takes to close a VC deal
(44:29) How AI is reshaping startup formation, team size, and funding trends
(48:11) Why VCs don’t like solo founders
(50:06) How employee equity (ESOPs) work
(53:50) Why acquisition payouts are often smaller than employees expect
(55:06) Deep tech vs. software startups:
(57:25) Startup advisors: What they do, how much equity they get
(1:02:08) Why time between rounds is increasing and what that means
(1:03:57) Why it’s getting harder to get from Seed to Series A
(1:06:47) A case for quitting (sometimes)
(1:11:40) How to evaluate a startup before joining as an engineer
(1:13:22) The skills engineers need to thrive in a startup environment
(1:16:04) Rapid fire round
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The Pragmatic Engineer deepdives relevant for this episode:
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See the transcript and other references from the episode at https://newsletter.pragmaticengineer.com/podcast
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What Founders Get Wrong About Scaling – With Carta’s CEO
Henry Ward, cofounder and CEO of Carta, has spent over a decade scaling his company from an early-stage startup to a 2,000-person industry leader. In this a16z Speedrun conversation with Games partner Josh Lu, Henry shares hard-earned lessons on:
Hiring missionaries vs. mercenaries — and how to keep company culture intact as you scale
The reality of product-market fit and why many founders try to sell too soon
The evolution of a CEO — from building a product to building a system around you
Inputs vs. outputs, and why companies should focus on the right leading indicators
Transparency in leadership, including when (and when not) to share
This episode is packed with candid insights and lessons on company building. Recorded live at the a16z Speedrun program, you can learn more at a16z.com/games/speedrun.
Resources:
Find Henry on X: https://x.com/henrysward
Find Josh on X: https://x.com/JoshLu
Stay Updated:
Let us know what you think: https://ratethispodcast.com/a16z
Find a16z on Twitter: https://twitter.com/a16z
Find a16z on LinkedIn: https://www.linkedin.com/company/a16z
Subscribe on your favorite podcast app: https://a16z.simplecast.com/
Follow our host: https://twitter.com/stephsmithio
Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
Stay Updated:
Find a16z on YouTube: YouTube
Find a16z on X
Find a16z on LinkedIn
Listen to the a16z Show on Spotify
Listen to the a16z Show on Apple Podcasts
Follow our host: https://twitter.com/eriktorenberg
Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
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SaaStr 771: The Top Marketing Strategies for 2025 Growth with the CMOs of Snowflake, LinkedIn, and Carta
SaaStr 771: The Top Marketing Strategies for 2025 Growth with the CMOs of Snowflake, LinkedIn, and Carta
Right now is one of the hardest times of the year for marketers. Most CMOs will be heads down wrapping up a year-end assessment and figuring out what to pitch for next year's budgetary spend to drive revenue, all while navigating an ever-changing environment of inconsistent metrics, lower conversion rates, and a rapid rate of change with the adoption of AI in SaaS.
A CMO panel consisting of the CMO of Snowflake, Denise Persson, CMO of Carta Nicole Baer, and the VP of Marketing at LinkedIn for Sales, Gail Moody-Byrd all answer Carilu Dietrick's questions, CMO and advisor formerly at Atlassian, about all things growth for 2025.
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Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code NOVEMBER20 for an extra discount on our very best pricing.
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Market Update: Peter Walker on 2023 VC Valuation Trends, Dry Powder, New Bubbles, Employee Trends
Subscribe to my newsletter The Split for new episodes emailed every week: https://www.thespl.it/
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Peter Walker is Head of Insights at Carta and writes a newsletter called “The Data Minute”, a weekly newsletter highlighting data from over 43,000 private tech companies that use Carta’s platform to manage their cap table. He gives us into a deep dive on VC valuation trends, the fundraising landscape, and startup strategies.
Timestamps:
(00:00) Intro
(04:50) Valuation trends in 2023
(08:10) Why Seed valuations went up over the past two years
(12:27) AI startups are getting higher valuations
(17:40) Why Biotech might be the next big bubble
(19:15) Boston as the 2nd largest VC ecosystem
(21:15) How SAFE’s work
(24:06) The impending SAFE reckoning
(26:13) Why startups don’t pay dividends
(28:31) Downrounds were 2x more common in 2023
(32:11) Almost half of all 2023 Series As were extensions
(35:34) Is there really a lot of dry powder?
(40:43) The emerging manager fundraising landscape
(48:19) Exit environment
(51:45) Why pre-Series B is the most common acquisition stage
(52:47) Liquidation preference & why an acquisition at Seed might make a founder more money than at a Series B
(55:59) Compensation market data
(56:38) Why the number of total startup employees shrank in 2023
(57:38) Why startup employees aren’t exercising their options
(1:00:57) Health of the secondary markets
(1:04:51) Most co-founder splits aren’t 50/50
(1:06:47) Why you should always vest co-founder equity
(1:09:30) 2023 record year for startup shutdowns
(1:17:19) Will other startup ecosystems ever catch Silicon Valley?
Links:
Carta’s Q4 ‘23 Private Market Report: https://carta.com/blog/state-of-private-markets-q4-2023/
Peter’s Newsletter: https://carta.com/subscribe/data-newsletter-sign-up/
Where to find Peter:
Twitter: https://twitter.com/PeterJ_Walker
LinkedIn: https://www.linkedin.com/in/peterjameswalker/
Where to find Turner:
Twitter: https://twitter.com/TurnerNovak
LinkedIn: https://www.linkedin.com/in/turnernovak/
Newsletter: https://www.thespl.it/
The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)
Will Larson is Chief Technology Officer at Carta. Prior to joining Carta, he was the CTO at Calm and held engineering leadership roles at Stripe, Uber, and Digg. He is the author of two foundational engineering career books, An Elegant Puzzle and Staff Engineer, and The Engineering Executive’s Primer, which will be released in February. In our conversation, we discuss:
• Systems thinking: what it is and how to apply it
• Advice for product managers on fostering productive relationships with engineering managers
• Why companies should treat engineers like adults
• How to best measure developer productivity
• Writing and its impact on his career
• How to balance writing with a demanding job
• How to develop your company values
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Find the full transcript at: https://www.lennysnewsletter.com/p/the-engineering-mindset-will-larson
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Where to find Will Larson:
• X: https://twitter.com/Lethain
• LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/
• Website: https://lethain.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Will’s background
(04:12) Changes in the field of engineering
(06:27) We need to stop treating engineers like children
(08:32) Systems thinking
(13:23) Implementing systems thinking in hiring
(16:32) Engineering strategy
(20:21) Examples of engineering strategies
(25:08) How to get good at strategy
(26:48) The importance of writing about things that excite you
(32:40) The biggest risk to content creation is quitting too soon
(35:24) How to make time for writing
(37:41) Tips for aspiring writers
(41:18) Building productive relationships between product managers and engineers
(43:45) Giving the same performance rating to EMs and PMs
(48:24) Measuring engineering productivity
(55:53) Defining company values
(01:02:10) Failure corner: the Digg rewrite
(01:11:05) Will’s upcoming book, The Engineering Executive’s Primer
(01:12:04) Lightning round
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Referenced:
• The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom
• Work on what matters: https://lethain.com/work-on-what-matters/
• Sheryl Sandberg to Harvard Biz Grads: “Find a Rocket Ship”: https://www.forbes.com/sites/kashmirhill/2012/05/24/sheryl-sandberg-to-harvard-biz-grads-find-a-rocket-ship/?sh=708c9a93b37a
• What Is Systems Thinking?: https://www.snhu.edu/about-us/newsroom/business/what-is-systems-thinking
• Introduction to systems thinking: https://lethain.com/systems-thinking/
• Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557
• Silent Spring: https://www.amazon.com/Silent-Spring-Rachel-Carson/dp/0618249060
• Writing an engineering strategy: https://lethain.com/eng-strategies/
• Carta: https://carta.com/
• Eric Vogl on LinkedIn: https://www.linkedin.com/in/ericvogl/
• Good Strategy/Bad Strategy: The difference and why it matters: https://www.amazon.com/Good-Strategy-Bad-difference-matters/dp/1781256179
• The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/
• How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/
• Technology Strategy Patterns: Architecture as Strategy: https://www.amazon.com/Technology-Strategy-Patterns-Architecture/dp/1492040878/
• The Value Flywheel Effect: Power the Future and Accelerate Your Organization to the Modern Cloud: https://www.amazon.com/Value-Flywheel-Effect-Accelerate-Organization/dp/1950508579
• The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win: https://www.amazon.com/Phoenix-Project-DevOps-Helping-Business/dp/1942788290
• The Engineering Executive’s Primer: Impactful Technical Leadership: https://www.amazon.com/Engineering-Executives-Primer-Impactful-Leadership/dp/1098149483
• An Elegant Puzzle: Systems of Engineering Management: https://press.stripe.com/an-elegant-puzzle
• Staff Engineer: Leadership beyond the management track: https://www.amazon.com/Staff-Engineer-Leadership-beyond-management-ebook/dp/B08RMSHYGG
• Gergely Orosz’s newsletter: https://blog.pragmaticengineer.com/author/gergely/
• Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer): https://www.lennyspodcast.com/videos/leaving-big-tech-to-build-the-1-technology-newsletter-gergely-orosz-the-pragmatic-engineer/
• The art of product management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo): https://www.lennyspodcast.com/videos/the-art-of-product-management-shreyas-doshi-stripe-twitter-google-yahoo/
• Henry Ward on LinkedIn: https://www.linkedin.com/in/heward/
• Vrushali Paunikar on LinkedIn: https://www.linkedin.com/in/vrushali-paunikar/
• Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339
• How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennyspodcast.com/how-to-measure-and-improve-developer-productivity-nicole-forsgren-microsoft-research-github-goo/
• DORA: https://dora.dev/
• Setting engineering org values: https://lethain.com/setting-engineering-org-values/
• Digg: https://digg.com/
• Kevin Rose on LinkedIn: https://www.linkedin.com/in/kevinrose/
• Digg’s v4 launch: an optimism born of necessity: https://lethain.com/digg-v4/
• Dash Gopinath on LinkedIn: https://www.linkedin.com/in/dashgopinath/
• Rich Schumacher on LinkedIn: https://www.linkedin.com/in/richschumacher/
• The ALL NEW Don’t Think of an Elephant!: Know Your Values and Frame the Debate: https://www.amazon.com/ALL-NEW-Dont-Think-Elephant-ebook/dp/B00NP9LHFA
• Top Chef on Peacock: https://www.peacocktv.com/watch-online/tv/top-chef/5172289448907967112
• Hard to work with: https://lethain.com/hard-to-work-with/
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Lenny may be an investor in the companies discussed.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe
Charting the future of the early-stage venture market with Carta’s CEO
This week, we had Carta CEO Henry Ward on to chat through the early-stage market with us.
Alex had a grip of data and a sheaf of questions, so here's what we got into:
The current state of the early-stage venture capital market: From Ward's perspective, the early-stage market is in better shape than many folks think. It's the later-stages of venture capital that are the most moribund. We also riffed on the quality of startups that are raising today, and how much pain is coming for young tech companies that can't quite attract more capital.
Carta's new Seed and Series A product: Carta is offering a mostly-automated method of closing early-stage rounds; we wanted to better understand the economics of the effort, and what the unicorn hopes to achieve from the work.
We closed with a look ahead, and a series of fun closing questions with Ward.
That's just the high-level summary. We also discussed entrepreneurship more broadly, the importance of LLCs, and even how to construct a podcast interview.
Don't forget: our listener survey is back! Take a moment to let us know what you want more of, what you want less of, and how we can make this the kind of podcast you want to come back to every week. Chat soon!
For episode transcripts and more, head to Equity’s Simplecast website.
Equity drops at 7 a.m. PT every Monday, Wednesday and Friday, so subscribe to us on Apple Podcasts, Overcast, Spotify and all the casts. TechCrunch also has a great show on crypto, a show that interviews founders, one that details how our stories come together and more!
Credits: Equity is produced by Theresa Loconsolo with editing by Kell. Bryce Durbin is our Illustrator. We'd also like to thank the audience development team and Henry Pickavet, who manages TechCrunch audio products.
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Henry Ward - Transforming Private Markets - [Invest Like the Best, EP. 273]
My guest today is Henry Ward, co-founder and CEO of Carta. Started in 2012, Carta helps companies and investors manage their cap tables, equity plans, and ownership. Last year, they launched CartaX, a platform for private companies and their employees to access secondary market liquidity. Our discussion is a detailed exploration of private market infrastructure and Henry’s views on building an enduring business. Please enjoy my conversation with Henry Ward.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Show Notes
[00:02:57] - [First question] - The first key mental moment of how Carta came to him
[00:05:30] - Initial thoughts on how to position Carta as a business model
[00:06:47] - Historical divergence between private and public market infrastructure
[00:08:33] - What a price discovery process for primary shares could look like in the future
[00:11:09] - The end state Carta is trying to effect in their perfect state
[00:13:29] - Why it’s so hard for private company staff to manage their illiquid wealth
[00:15:45] - Lessons and challenges in the new market creation business
[00:17:57] - The nature and dynamics of supply and demand in this space
[00:22:45] - How Carta is mapped onto the success of its customers
[00:25:27] - Deciding on what is a good idea and what isn’t when it comes to focus
[00:28:07] - Describing the One of N versus N of One market frameworks and principles of this philosophy that manifests in how he runs Carta
[00:32:11] - How working at Carta would differ from a payroll-type company
[00:35:37] - Characterizing his leadership and management styles
[00:37:57] - The types of circumstances that bring out his tough side
[00:39:33] - Making hard decisions in a bottom up management model
[00:44:05] - How he spends his time while building Carta
[00:45:02] - What a great product looks like to him
[00:47:10] - The Systems Bible; Defining what a great team looks like
[00:49:13] - What he’s learned about being great at Go-To-Market
[00:51:26] - Effective ways to beat competitors and build relationship pipelines
[00:53:49] - Things he likes the least about leading a company of this size
[00:55:13] - What he fears most as he thinks about the future of Carta
[00:55:45] - Advice for entrepreneurs when thinking about data in modern businesses
[00:58:26] - The biggest missing pieces in capital market structure writ large
[01:00:17] - What’s next for CartaX and what he’ll be pushing to make it work
[01:02:10] - Lessons learned from serving venture investors
[01:04:25] - Whether or not investment banks are their competitors
[01:05:18] - Public market dislocation and how long it will last
[01:06:58] - The kindest thing anyone has ever done for him
20VC: Portfolio Construction, Optimising SPVs, Opportunity Investing "Between Rounds", Being Distribution-Centric Over Product-Centric and Capital Concentration Within Funds With Sumeet Gajri, Chief Strategy Officer @ Carta
Sumeet Gajri is the Chief Strategy Officer @ Carta, the startup that helps companies and investors manage their cap tables, valuations, investments, and equity plans. Sumeet is largely responsible for all things fundraising and M&A and Carta have raised over $485m from a16z, USV, Thrive, Spark, K9, Lightspeed and Meritech to name a few. Sumeet is also Managing Partner @ Original Capital, where he has partnered with companies including Front, Tonal, Instabase, Everlywell and Cockroach Labs to name a few. Finally, Sumeet is also an LP in world-leading firms such as USV and Valar Ventures.
In Today's Episode You Will Learn:
1.) How Sumeet made his first foray into the world of venture in NYC having grown up in Scotland? How that led to his move to operations with Carta? How his learnings from Carta led to his establishing Original Capital?
2.) How is Original Capital different from every other micro-fund? How does Sumeet approach portfolio construction with the fund? What is the optimal number in a portfolio? How does Sumeet think about loss ratio? What 3 criteria dos every new investment have to pass to make it into the portfolio? How does check size vary by deal?
3.) How does Sumeet invest in some of the best companies in between "official rounds"? What does this conversation look like with the founders? How does Sumeet analyse reserve allocations? What makes the right strategy? What are his capital concentration limits per company? How does Sumeet think about using SPVs effectively?
4.) Sumeet helps his companies fundraise a lot, what does the first step look like? How does he advise on investor selection? How does he advise on pipeline management? Should founders speak to investors when they are not raising? How open should they be in these meetings? What can founders do to catalyse the process? Where does Sumeet see many founders make mistakes?
5.) How does Sumeet think about distribution vs product? What can founders do to adopt a more distribution first mindset? What have been some of Sumeet's biggest lessons in turning Carta from a single product company to a multi-product company? Do companies have to own their own lines of distribution today?
Items Mentioned In Today's Show:
Sumeet's Fave Book: Howard Marks: The Value of Predictions
As always you can follow Harry, The Twenty Minute VC and Sumeet on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Part 3: An Elegant Puzzle Book Discussion w/ Will Larson
In today's episode ,we release part 1 of a three part interview with Will Larson. Will is an engineering manager at Stripe, and he recently published a book titled, An Elegant Puzzle: Systems of Engineering Management.
In this part 3, we discuss focus and how Will built depth in your career journey.
Get in touch
If you have questions about today's episode, want to start a conversation about today's topic or just want to let us know if you found this episode valuable I encourage you to join the conversation or start your own on our community platform Spectrum.chat/specfm/developer-tea
🧡 Leave a Review
If you're enjoying the show and want to support the content head over to iTunes and leave a review! It helps other developers discover the show and keep us focused on what matters to you.
🍵 Subscribe to the Tea Break Challenge
This is a daily challenge designed help you become more self-aware and be a better developer so you can have a positive impact on the people around you. Check it out and give it a try at https://www.teabreakchallenge.com/.
Part 2: An Elegant Puzzle Book Discussion w/ Will Larson
In today's episode ,we release part 1 of a three part interview with Will Larson. Will is an engineering manager at Stripe, and he recently published a book titled, An Elegant Puzzle: Systems of Engineering Management.
In this part 2, we dig into common patterns that help us create a fair evaluation system.
Get in touch
If you have questions about today's episode, want to start a conversation about today's topic or just want to let us know if you found this episode valuable I encourage you to join the conversation or start your own on our community platform Spectrum.chat/specfm/developer-tea
🧡 Leave a Review
If you're enjoying the show and want to support the content head over to iTunes and leave a review! It helps other developers discover the show and keep us focused on what matters to you.
🍵 Subscribe to the Tea Break Challenge
This is a daily challenge designed help you become more self-aware and be a better developer so you can have a positive impact on the people around you. Check it out and give it a try at https://www.teabreakchallenge.com/.
🙏 Thanks to today's sponsor: GitPrime
Our sponsor GitPrime published a free book - 20 Patterns to Watch for Engineering Teams - based data from thousands of enterprise engineering teams. It’s an excellent field guide to help debug your development with data.
Go to GitPrime.com/20Patterns to download the book and get a printed copy mailed to you - for free. Check it out at GitPrime.com/20Patterns.
Part 1: An Elegant Puzzle Book Discussion w/ Will Larson
In today's episode ,we release part 1 of a three part interview with Will Larson. Will is an engineering manager at Stripe, and he recently published a book titled, An Elegant Puzzle: Systems of Engineering Management.
In this part 1, we dig into why Will chose that title and about his developer journey.
Get in touch
If you have questions about today's episode, want to start a conversation about today's topic or just want to let us know if you found this episode valuable I encourage you to join the conversation or start your own on our community platform Spectrum.chat/specfm/developer-tea
🧡 Leave a Review
If you're enjoying the show and want to support the content head over to iTunes and leave a review! It helps other developers discover the show and keep us focused on what matters to you.
🍵 Subscribe to the Tea Break Challenge
This is a daily challenge designed help you become more self-aware and be a better developer so you can have a positive impact on the people around you. Check it out and give it a try at https://www.teabreakchallenge.com/.
20VC: Carta Founder Henry Ward on Why The Best Companies Are Not Product Led But Distribution Led, 3 Requirements Needed For A New Market/Investment To Be Exciting and Why Small Markets Are So Attractive
Henry Ward is the Founder & CEO @ Carta, the startup that helps private companies, public companies, and investors manage their cap tables, valuations, investments, and equity plans. To date, Henry has raised over $147m in funding from some of the industries leading investors in USV, Spark, K9 Ventures and Meritech and then also leading founders including Flexport's Ryan Petersen, Transferwise's Taavet Hinrikus and Slack's Stewart Butterfield. Prior to founding Carta, Henry was Founder of SecondSight, a portfolio optimization platform for retail investors.
In Today's Episode You Will Learn:
1.) How Henry made his way into the world of startups and came to found the gamechanger of cap tables and valuations with Carta?
2.) What does Henry mean by the term "executive half-life"? How does Henry determine between an exec that can scale with the company and an exec that cannot? What are the leading indicators? When weaknesses are revealed, how does this manifest itself? Does the exec open up and admit to it or does the leadership team have to be proactive?
3.) Question from Manu @ K9: As a first time CEO, what have been the biggest personal challenges for Henry in the scaling of himself? Why does Henry think it is unfair founders are given exemption from blame in scaling but execs are not? How does Henry make decisions differently now to the early days? What have been the improvements?
4.) How does Henry buck the conventional wisdom with his willingness to go after very small markets? What does the N of 1 vs 1of N rule mean here? Why does Henry believe the N of 1 markets is the most attractive? What are the core advantages to owning your market? How can founders think about insertion points? When is the right time to add additional products? How does Henry respond to the traditional notion of "focus"?
5.) Why does Henry believe most founders are afraid to put investors to work? If fundraising is, as Henry suggests "an auction process", what can founders do to optimise it? How does Henry approach the element of value creation and value extraction? How does this influence his approach to pricing? How does Henry think more tech founders can leverage acquiring services businesses and automating their processes over time? Where is the arbitrage in pricing here?
Items Mentioned In Today's Show:
Henry's Fave Book: The Essays of Warren Buffett: Lessons for Corporate America
As always you can follow Harry, The Twenty Minute VC and Henry on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
20VC: eShares' Henry Ward on Why Portfolio Theory Is Wrong? Why Investors Will Never Take Market Risk & Why You have To Have A Line of Sight To A $Bn Outcome
Henry Ward is the Founder & CEO @ eShares, the No 1 cap table management platform providing equity management, 409A valuations and liquidity all in one place. They are backed by leading investors and past guests including USV, SV Angel, Spark Capital, Semil Shah, Manu Kumar, Tim Draper and Kamal Ravikant, just to name a few. Prior to eShares, Henry was Founder @ SecondSight, the first registered investment advisor to go direct to your brokerage and improve your portfolio.
In Today's Episode You Will Learn:
1.) How Henry made his way into the world of startups and came to found eShares?
2.) How does Henry challenge the notion that investors should have such high fail rates? How does Henry believe investors can build a strong and sustainable portfolio without home runs?
3.) Why does Henry believe that investors will never accept market risk? How much of a role does Henry believe herd mentality plays in the VC ecosystem?
4.) How does Henry view the increasing exit horizons for startups? Is this a problem? How can we create liquidity options pre large exits?
5.) How does Henry view the role of regulation in private markets? How does this differ to public markets? What would Henry like to see change in the VC ecosystem?
Items Mentioned In Today's Show:
Henry's Fave Blog: Hacker News
Henry's Fave Book: The Essays Of Warren Buffett
As always you can follow Harry, The Twenty Minute VC and Henry on Twitter here!
Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.
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