20VC: Cohere Founder on How Cohere Compete with OpenAI and Anthropic $BNs | Why Counties Should Fund Their Own Models & the Need for Model Sovereignty | How Sam Altman Has Done a Disservice to AI with Nick Frosst

Rachel Carlson is the Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. To date, Rachel has raised over $71m in funding with Guild from some of the best in venture with the likes of Michael Dearing @ Harrison Metal, Wes Chan @ Felicis, Byron Deeter @ Bessemer, Aileen @ Cowboy Ventures and Scott Raney @ Redpoint, all backing Guild. As for Rachel, prior to Guild, Rachel was the Founder of Student Blueprint, providing students with academic and career planning tools. In Today's Episode You Will Learn: 1.) How Rachel made her way into the world of startups having started her career in politics and how insights gleaned from politics formed the idea for Guild Education? 2.) Why does Rachel believe that ambitious Mums are the most under-utilized asset in the economy? What are the biggest misconceptions people have about hiring and working with Mums? How can founders really implement practically facilities, tools and an environment where one can be both ambitious personally and professionally? 3.) Before the show, Byron Deeter @ Bessemer said, "Rachel has been among the best at recruiting star execs across their portfolio". What have been Rachel's biggest lessons when it comes to hiring the very best talent? Where do most go wrong? How has her hiring style changed over the years? What are Rachel's favourite questions to ask candidates? 4.) Why does Rachel believe that mission and margin are tightly integrated? How did Rachel acquire Walmart as one of their first clients? What are the positives and negatives of having a client so huge, so early? What advice would Rachel have for other early-stage companies when they have such behemoths as clients in the early days? 5.) Why did Rachel make the move from SF to Colorado? What did Rachel strategically do to ensure the chances of success were higher? How does Rachel feel about keeping leadership teams in SF and then the rest elsewhere? How did the move impact their ability to hire the best talent? How did their move impact their ability to access the best capital? Between customers, capital and employees, who is it most important to be near? Items Mentioned In Today's Show: Rachel's Fave Book: To the End of June: The Intimate Life of American Foster Care, Where The Crawdads Sing As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

11 Okt 201934min

John Fein is the Founder and Managing Partner @ Firebrand Ventures, one of the leading early-stage funds in the midwest with a portfolio including the likes of ScaleFactor, Replica, Dwolla and more fantastic companies. As for John, prior to founding Firebrand, he was the Managing Director of Techstars based in Kansas City and before that spent close to 9 years at OptumRx where he managed multi-billion dollar large-scale programs for the $15B pharmacy benefit manager division of UnitedHealth Group. In Today's Episode You Will Learn: 1.) How John made his way into the world of venture from scaling a pharmaceuticals business to almost $2Bn in revenue and how that led to founding Firebrand? 2.) What was it like for John raising the first fund for Firebrand with no existing network of LPs or high-net-worth individuals? How did John approach his closing strategy? How did he decide the amount of money to raise for the fund? How did Techstars Founder, David Cohen change and impact his thinking here? Was John surprised by how long the fund took to raise? 3.) What does John know now that he wishes he had known at the beginning of the fundraise for the first fund? Does it ever get easier? What does John believe are the biggest challenges in managing your own fund? What does he do to mitigate them? How does running your own fund differ from operating in a venture partnership? 4.) "Seed" is so confused in meaning today so what does "seed stage" really mean to John? Does John agree with Harry that we are seeing the eradication of the pre-seed stage? Where does John believe is the ideal insertion point? Does John believe that ownership can be built over time? How does John think about reserve allocation? 5.) How does John think about the relationship-building process with founders? Is John worried by the compressed fundraising timelines we are seeing today? What can investors do to build trust with founders quickly? What signs impress John in the early days of getting to know the founder? What are some common red flags for John? Items Mentioned In Today's Show: John's Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna John's Most Recent Investment: The Minte As always you can follow Harry, The Twenty Minute VC and John on Twitter here!

7 Okt 201939min

Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame. In Today's Episode You Will Learn: 1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel? 2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here? 3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far? 4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do? Items Mentioned In Today's Show: Jason's Fave Book: Meditations by Marcus Aurelius As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

4 Okt 201939min

Brad Feld is Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio that includes the likes of Zynga, Fitbit, SendGrid and many more incredible companies. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars, the worldwide network of entrepreneurs in 150 countries and 300,000 alumni. Brad is also the co-author of the incredible, Venture Deals, for your chance to win a signed copy email venturedeals@foundrygroup.com with the code "First Episode". In Today's Episode You Will Learn: 1.) How Brad made his way into the world of venture following 40 angel checks and how that led to his co-founding Foundry Group? Why did Brad find the transition from angel to VC in the early days such a challenge? What 2 core things did he focus on when writing angel checks? How has that changed now as a VC? 2.) How did seeing the boom and bust of the dot com impact Brad's investing mindset today? How does Brad think about investing through market cycles and the right way to think about investment cadence? Why does Brad believe that to be successful as a VC you have to be fundamentally optimistic? 3.) Where does Brad believe we are today in the cycle? Does he agree with Bill Gurley on the biggest challenge being the "oversupply of capital"? What must entrepreneurs understand with regards to market cycle dynamics and how they can and need to future-proof their business? 4.) From analysing his best investments, why has Brad come to the conclusion that TAM in the early days is really not helpful? What are the commonalities in how Brad's most successful companies approach experimentation? 5.) What does Brad mean when he says, "don't have fake CEO or fake VC days"? What does he mean when he often says, "run your fucking business"? What in Brad's mind would constitute a "fake day" vs moving the needle for your business? What does Brad think is the best way for VCs to truly get to know one another? Why is, "hey let's do a deal together one of the most hollow and fake statements in venture?" 6.) Brad has sat on some of the most meaningful boards of the last 2 decades, what have been Brad's biggest learnings on what it takes to be a great board member? How does that change with the progression of your career? What advice would Brad give to me, having just gained my first board seat? If the VC does not support the CEO, what is the right process? Why does Brad believe the VC should work for the CEO? 7.) What is Brad's biggest advice when it comes to learning how to say no? What advice does Brad hear most often that he commonly disagrees with? Why does Brad feel we are in a moment of peak noise in the ecosystem today? To be a great leader, what 2 skills does Brad believe you need to have? Items Mentioned In Today's Show: Brad's Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna, The Moment of Lift: How Empowering Women Changes the World by Melinda Gates Brad's Most Recent Investment: Boundless As always you can follow Harry, The Twenty Minute VC and Brad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

30 Sep 201950min

Julia Enthoven is the Founder & CEO @ Kapwing, the startup that provides a new, collaborative platform for creating images, videos, and GIFs. To date they have raised $13m from some dear friends of the show including Saar Guur @ CRV, Mamoon Hamid @ Kleiner Perkins, Niv Dror @ Shrug and Nikhil Basu Trivedi @ Shasta. Prior to founding Kapwing, Julia was an Associate Product Manager @ Google where she worked on everything from image search to sign up workflows. In Today's Episode You Will Learn: 1.) How Julia made her way into the world of startups and came to found the future of content editing with Kapwing? 2.) What does Julia believe are the 4 benefits to building a website over an app today? How does this change your development cadence and speed of product iteration? How does this change your economics and margin structure? Where does Julia see many founders making mistakes here? 3.) Why does Julia believe that marketing innovation is as important as product innovation? Kapwing is now at 1m users per month, what has been Julia's biggest lessons in scaling a customer base to this size with very little spend? How does Julia think about marketing channel mortality rate? How should founders approach this? 4.) Why did Julia decide it was better to bootstrap than straight away trying to raise VC dollars? What were the benefits of this? Was it the right decision? What was the turning point when Julia realised was the moment to raise external funding? How did her mindset change as a result of the funding? How does bootstrap life compare to VC funded startup? 5.) How is Julia finding the personal scaling journey from PM to CEO? What have been some of the biggest challenges? What has she done to overcome them? What advice would Julia have for other newly minted CEOs? What have been some of Julia's biggest lessons in what it takes to hire the very best talent early? Items Mentioned In Today's Show: Julia's Fave Book: Influence: The Psychology of Persuasion As always you can follow Harry, The Twenty Minute VC and Julia on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

27 Sep 201933min

Matt Harris is a Partner @ Bain Capital Ventures, a leading US venture fund with a portfolio that includes the likes of LinkedIn, Lime, SendGrid, Jet.com and more incredible companies. As for Matt, he specialises in financial technology and services and has led investments in the likes of Acorns, OpenFin, SigFig, Ribbon and Billtrust. Prior to joining BCV, Matt founded Village Ventures, which he ran for 12 years and where he focused on early-stage fintech investing. Before Village Matt actually started his investing career Bain Capital private equity in 1995. In Today's Episode You Will Learn: 1.) How Matt made his way into the world of venture from private equity and what led him to specialise as he has done in the world of fintech? 2.) How did seeing the boom and bust of the dot com impact Matt's investing mindset today? How has Matt's fear of the cyclicality of markets actually lost him a lot of money in the past? What has that taught Matt on trying to time markets? What were the main takeaways for Matt from running his own firm? How does it differ to a partnership? 3.) Why does Matt believe we are seeing late-cycle momentum investing today? What is the evidence to suggest this? How does Matt think about the right cadence to invest through market cycles? What does Matt mean when he says, "Series A valuation does not matter anymore"? Why? How does Matt assess his own price sensitivity today? 4.) Why does Matt believe that investing in improbable ideas is a good strategy? What does this mean the internal investment decision-making process looks like at Bain? Why is full consensus sometimes a concern? How does Matt approach market sizing? Why does it not matter at Series A? When does it really start to matter? 5.) Matt has said before that "backing sociopaths can work". What did he mean by this? What founder type does Matt most like to back? Does one have to manage the relationship with them very differently to other founder types? What are the acceptable risks vs unacceptable risks with this founder type? Items Mentioned In Today's Show: Matt's Fave Book: The Third Plate: Field Notes on the Future of Food Matt's Most Recent Investment: Finix As always you can follow Harry, The Twenty Minute VC and Matt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

23 Sep 201935min

Immad Akhund is the Founder & CEO @ Mercury, the startup that makes bank accounts that help tech companies scale. To date, Immad has raised funding from some of the best in the business including a16z and CRV on the fund side and then individuals including Elad Gil, Airtable's Howie Liu, Plaid's Zach Perret, Naval Ravikant, Justin Kan and OpenDoor's Eric Wu. Prior to founding Mercury, Immad held enjoyed numerous different roles including being a part-time partner at Y Combinator and then also founding HeyZap, building developer tools for mobile game developers, ultimately acquired in 2016. In Today's Episode You Will Learn: 1.) How Immad made his way from studying in the UK to being a YC Partner in 2017 and building one of the valley's hottest startups today in the form of Mercury? 2.) What does Immad want to do differently this time around with Mercury vs his time with HeyZap? What 1-2 mistakes that he made the first time round is Immad looking to avoid? How does being a serial founder impact one's ability to acquire the best talent? What does Immad think is harder the second time around? How has becoming a parent changed the way that Immad thinks about founding and building companies? 3.) How does Immad approach the process of picking the idea? What was the specific process with Mercury, step by step? Why does Immad believe it is an advantage to not have a background or prior career in the space you are looking to innovate in? What advice does Immad have for founders looking to move into highly regulated industries? 4.) How does Immad approach and assess the element of competition? What is the right way for founders to present competition when pitching to investors? Why is a 2x2 matrix the wrong approach? What does Immad advise portfolio founders he has invested in with regards to competition and the landscape in front of them? 5.) What have been some of Immad's biggest learnings from making over 120 angel investments? How has angel investing specifically helped certain parts of how he thinks about operating and being a founder today? What advice does Immad give with regards to investor updates? What makes the best ones? What makes the worst? How often should they be? Items Mentioned In Today's Show: Immad's Fave Book: The Accidental Superpower: The Next Generation of American Preeminence and the Coming Global Disaster As always you can follow Harry, The Twenty Minute VC and Immad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20 Sep 201934min

Semil Shah is the Founder & General Partner @ Haystack, one of the valley's leading seed funds of the last 5 years with a portfolio including the likes of Instacart, DoorDash, Carta, OpenDoor, Hashicorp and more $Bn companies. Alongside his role at Haystack, Semil is also a Venture Partner @ Lightspeed Venture Partners. Prior to founding Swell, Semil was on the operating side as an early advisor and employee at Concept.io (Swell), acquired by Apple in August 2014. In Today's Episode You Will Learn: 1.) How did Semil make his way into the world of venture from his start writing about startups and financing rounds? How did that also lead to his role as Venture Partner @ Lightspeed today? 2.) What does Semil mean when he says, "the most talented founders are bypassing seed firms and seed rounds"? How does this mean that seed funds need to respond? For founders, what are the pros and cons of taking a multi-stage fund at seed? Will they really get GP time with such a small check? How should they also think about potential signalling risk? 3.) Does Semil share Harry's concern with regards to pricing today? What do multi-stage funds investing at seed do to pricing? Why is staying disciplined on price the biggest challenge for Semil? How does Semil assess his own price sensitivity and when to stretch? Does Semil believe that ownership is built on first check or overtime? 4.) How does the strategy for Semil change moving from a $25m fund to a $50m fund? Why does Semil think that temporal diversification is such an important element to bake into a portfolio? What are the benefits? How does Semil think about effective reserve allocation today? What does that investment decision-making process look like the 2nd time? 5.) How has Semil seen the ecosystem for VC fundraises change over the last 5 years? What would Semil like to change about the ecosystem of LPs? What blanket rule does Semil believe that LPs should introduce for new managers to ensure discipline? For Semil, how did the fundraise differ for the latest $50m fund compared to the prior $25m fund? Items Mentioned In Today's Show: Semil's Fave Book: Reboot by Jerry Colonna As always you can follow Harry, The Twenty Minute VC and Semil on Twitter her

16 Sep 201942min