The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most revolutionary products in society from the iPhone and iPod to more recently founding Nest, creating the Nest Thermostat, leading to their $3.2BN acquisition by Google. Tony recently released Build, a masterclass taking 30 years of product and company building lessons and packaging them for you, check it out here.

1.) On reflection, what would Tony most like to change about his childhood?

• How did moving so much as a child change who Tony was as a person?
• How can parents instill that same grit and desire in their kids today?
• What does Tony think is the biggest problem with modern parenting?

2.) As a leader, should the company you are building be a family or a team?

• What does Tony believe are the 3 hats of being a great CEO?
• What is the biggest challenge in the transition between hats?
• Where does Tony see many founders make the biggest mistake?
• Which hat was Tony strongest with? What was he weakest with?

3.) How to solve the loneliness of being a solo founder?

• Why does Tony believe that everyone needs a co-founder?
• Why does Tony not like to invest in teams with a solo founder or more than 4 founders?
• For Tony, what is the ideal composition of that founding team?
• How does he test for these skills and traits pre-investing?

4.) How to think differently in the face of adversity?

• Tony has made bold bets when everyone says he is crazy, how does he not question himself and remain strong in the face of criticism?
• How does Tony know when to change his mind? When to accept that the bold idea was not right?
• Is Tony concerned in the face of macro challenges today, investment and commitment to climate change will be cut heavily?

Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few. As for Kyle, before moving to the world of venture and crypto, he founded Pristine, a health IT startup that raised more than $5M in VC, and was acquired by Upskill.

1.) The Founding of Multicoin Capital:

• How did Kyle make his way from a healthcare startup to founding Multicoin?
• What was his a-ha moment with the realization of the opportunity we have ahead of us in crypto?
• What does Kyle know now that he wishes he had known when he started Multicoin?

2.) Crypto Investing in 2022:

• Why does Kyle believe the crypt investing landscape is less collaborative than ever?
• What are the biggest challenges of token issuances today?
• How does the option of liquidity help and hurt Kyle's investor psychology?
• Is Kyle concerned the volatility in the market will harm institutional investor sentiment for crypto?

3.) Constructing a Crypto Portfolio in 2022:

• Why does Kyle not believe in temporal diversification?
• Why does sector-centric company diversification suck?
• Why are the loss ratios in crypto so much lower than in traditional venture?
• Why does Kyle believe a no reserves model is optimal in crypto?

4.) Multicoin vs Traditional Venture Firms:

• Why does Kyle believe that every person over 10 people in a venture firm is a net negative towards the investment decision-making process?
• What do Kyle and Multicoin do reach the truth together? How do they aggressively use writing and word docs to progress their thoughts?
• Their discussions are "brutal", how brutal can one be in a discussion on a deal? How does one make team members feel safe but also really push them for the truth and debate?

Kyle's Favourite Recent Reading: Eugene Wei

Kyle's Most Recent Investment: Delphia

Sam Taylor is the VP of Sales and Customer Success @ Loom, an essential tool for hybrid and remote teams allowing you to record quick videos of your screen and cam. At Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist, Sales Development, Global Customer Support, Revenue Ops + Strategy and Sales Enablement. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader.

1.) Entry into the World of Sales:

• How did Sam land his first big role in sales at Salesforce?
• How did the sales orgs differ when comparing Salesforce to Dropbox?
• What are 1-2 of Sam's biggest lessons from his time at Salesforce and Dropbox that shapes how he thinks today?

2.) Sales People Should Be Customer Therapists:

• What is the right way to approach customer discovery?
• How can sales reps get potential customers on a call in the first place?
• What are the right questions to ask? What engenders the most honesty?
• What are the wrong questions to ask? What are common mistakes?
• How do the best sales reps then feed that back to customer success and product?

3.) The When and The Who:

• When should founders consider hiring their first sales hire?
• Should this hire be a sales leader or a sales rep? What are the nuances?
• What are the characteristics of the best first sales hires?
• What are the first sales hires really on the hook for?
• Why does Sam disagree with the word "playbook" and instead suggest "frameworks"?

4.) How To Hire The Best: The Process

• What are Sam's lessons on what it takes to hire the very best sales reps?
• What are the right questions to ask in the interview process?
• What tangible case studies or tests are done to measure quality?
• Who is brought into the hiring process and at what stage?

Des Traynor is a Co-founder and the Chief Strategy Officer of Intercom, the modern customer communications platform that unifies every aspect of the customer journey. To date, Intercom has raised over $238M from some of the best including Index, ICONIQ, Kleiner, GV, and Bessemer. As for Des, before co-founding Intercom, he was a UX consultant, a university lecturer in computer science, and also a Ph.D. researcher. Des is also a prolific angel investor with a portfolio including the likes of Stripe, Algolia, Notion, Miro, and many more.

1.) Origins of Intercom:

• How did Des make his way into the world of startups and come to co-found Intercom?
• When did they realize they really had something with Intercom and had to focus on it?
• What does Des know now that he wishes he had known at the start of Intercom?

2. Two of the Biggest Myths in Startups: Being First and Defensibility

• Why does Des believe that being the first does not matter? Why is it not an advantage?
• Why does Des believe that no company has defensibility on day 1? How does Des believe defensibility is built?
• What does Des mean when he says, when investing in companies he looks for a "long road to the starting line"?

3.) Product 101: A Masterclass on Product:

• How does Des answer the question of when to release a second product?
• How should the second product be resourced? MVP and lean or full budget and committed?
• What are the biggest mistakes people make when releasing a second product? What mistakes have Des and Intercom made when releasing new products?
• How does Des advise founders on when to stop working on a product? How do you know when it is not working?
• How does Des determine between a feature and a product both when building and when investing?

4.) Moving to Enterprise:

• What does Des believe are the three core things all companies need to scale into the enterprise effectively? Which should they do first? Which is most challenging?
• How does Des advise founders on when is the right time to move into the enterprise?
• How does the product need to change to meet enterprise needs and requirements?

5.) The Makings of Great Product Marketing:

• What does Des believe makes truly great product marketing? Who does it well today?
• How does your product marketing need to change as you scale from SMB to enterprise?
• If product marketing to both an end user and a separate buyer, which persona should one prioritise their messaging towards?
• How does Des advise founders on product marketing when they have a horizontal product with a very broad customer base?

6.) Angel Investing 101: From Stripe to Miro to Notion:

• Why does Des believe it is beneficial for operators to also be investing?
• What are the biggest lessons Des has learned from angel investing?
• How does Des approach both market sizing and outcome scenario planning today?
• How price sensitive is Des today? How has that changed over time?

Des' Favourite Book: How Will You Measure Your Life by Clayton Christensen

Peter Singlehurst is the Head of Private Companies at Baillie Gifford. As of 31st March 2022, funds under Baillie Gifford's management and advice totaled £277bn. The firm is owned and run by 51 of its senior executives who operate as a partnership, a structure that has endured for over a century. As for Peter, he has been with Baillie Gifford since graduating from Durham University 12 years ago and has backed some astonishing breakouts such as Wise, Grammarly and Zymergen to name a few.

1.) Entry into Venture:

• How Peter landed his role with Baillie Gifford straight out of university?
• Why does Peter and Baillie Gifford prefer to hire young people without backgrounds or studies in finance? Why do they tend to be better investors?
• What does Peter believe are the basic building blocks that can be taught in investing? What cannot be taught and needs to be learned with experience and time?

2.) The Biggest Misnomers and Misalignments in Venture:

• Why does Peter believe the distinction between public vs private markets is BS?
• Why does Peter believe it is an advantage to invest at the same time in both public and private markets?
• Why does Peter think there is an inherent misalignment in venture between GPs and their LPs?

3.) Baillie Gifford: Constructing a Portfolio with £277BN:

• How does Baillie Gifford approach portfolio construction today?
• How many lines do they want to have in their portfolio? What is the right level of diversification?
• How does Peter think about sizing each position? How does Peter think about capital concentration across rounds vs first check being the largest?
• How does Peter approach outcome scenario planning? How does Peter think about downside protection and loss rates?

4.) Peter Singlehurst: The Investor:

• How has Peter's investing style changed over the last 10 years? What has gotten easier? What has gotten harder?
• What is Peter's biggest miss? How did it change his approach?
• What is Peter's biggest hit? What did he learn and take from this?
• How did the crossover funds change and impact the way that later stage venture was conducted?

Peter's Fave Book: The Myth of Sisyphus

Peter's Most Recent Investment: Grammarly

Luc Levesque is currently the VP of Growth at Shopify and also advises companies like Twitter, Pinterest, and Quora. At the age of 21, Luc founded TravelPod, the world's first travel blogging platform. 10 years later, TravelPod was acquired by Expedia, where Luc led the creation of two award-winning products: TripWow and the Traveler IQ Challenge. Luc then served as an executive at TripAdvisor, where he built and led the growth team which helped TripAdvisor become the world's largest travel site. Luc was then recruited by Mark Zuckerberg to Facebook where he was an executive and led the creation of Messenger Kids.

1.) Entry into Growth:

• When did Luc realise the power of "growth" within every company?
• How did Luc subsequently make his way into the world of growth pose-selling his first company?
• What does Luc know now that he wishes he had known when he made the entry into growth?

2.) Growth and Viral Loops:

• How does Luc define "growth" today?
• How should leaders choose what is the right north star to focus on for their business?
• Should this north star change? If so, how often should the north star change?
• How does Luc define "viral loops"? What makes the best viral loops today?

3.) Growth: Building the Team:

• When is the right time for founders to start thinking about building a growth team?
• Should it be standalone or integrated into other functions in the company?
• Should the first growth hires be senior and tasked with hiring the team or junior and be more lean as a way to test growth as a new function?
• What are the signals Luc looks for when hiring for growth?
• What are the best questions that reveal the characteristics growth leaders need to have?

4.) Growth: The Action:

• What is a growth decision Luc made without data? How did it go?
• What are some growth tactics that have become stronger over time? What have died a death?
• How should leaders know when to kill a new project vs continue and keep testing?
• What are the biggest mistakes Luc sees founders make when building and scaling their growth team?

Matt Mullenweg is the Founder of Automattic, the force behind WordPress, Tumblr, WooCommerce, Jetpack, Longreads, Simplenote, Pocket Casts, and more. What started as a simple open-source blogging platform, Matt has turned into one of the most significant internet properties of our generation, now powering over 43% of sites on the internet. Alongside Automattic, Matt also invests through Audrey Capital and has backed the likes of Stripe, SpaceX, Gitlab, and Sendgrid to name a few.

1.) The Origins of WordPress:

• How did Matt start the for-profit, Automattic, as a 19-year-old, having been a lead developer for WordPress?
• What were the clearest signs to Matt in the early days that WordPress could change the world?
• What does Matt know now that he wishes he had known at the beginning of WordPress?

2.) Matt Mullenweg: The Essence of Leadership:

• What does high performance mean to Matt? How has that changed over time?
• What does truly great listening mean to Matt as a leader today? Where do many get this wrong?
• How does Matt approach decision-making today? What are the two types of decisions?
• What are Matt's biggest insecurities in leadership today? How have they changed over time?

3.) Matt Mullenweg: The Person:

• Why does Matt have insecurities around his body? How do those insecurities manifest?
• What did Matt learn about himself in the pre-grieving process before his father's passing?
• How does Matt assess his own relationship to risk today?
• How does Matt think through his relationship to money today? Has it changed?

4.) WordPress: The Company:

• Why did Matt decide it was the right decision to buy Tumblr? Why did Matt make himself the CEO earlier this year?
• With many strong cashflow businesses within Automattic, how does Matt think through the balance between growth and profitability?
• Why does Automattic not have any emails within the company? How do 2,000 people communicate so effectively?

Matt's Favourite Book: Principles by Ray Dalio

Mike Chalfen is a solo GP with Chalfen Ventures and one of the most respected and successful early-stage investors in Europe over the last two decades. Among Mike's incredible portfolio includes the likes of King.com (makers of Candy Crush), Houzz, Tipalti, Snyk, and Tray.io, to name a few. Some incredible facts on Mike, he has a 15x career track record, he has a portfolio value of over $40BN+ and he joined the venture industry, the year of my birth!

1.) Entry Into Venture and The Broken Customer Experience of VC:

• How did Mike make his original entry into venture way back in 1996?
• What does Mike mean when he speaks of the difference between "managing your career vs the money you invest"?
• What does Mike believe are some of the greatest challenges of venture partnerships today?
• What does Mike believe that the customer experience in venture partnerships for founders is broken today?
• How did seeing the prior booms and busts impact Mike's investing mentality today?

3.) Portfolio Construction 101:

• How does Mike think about portfolio construction today?
• With 9-10 core positions, why does Mike disagree with the traditional notion of "diversification"?
• How does the decision-making framework for Mike change when considering new investments vs re-investments?
• Does Mike believe that pro-rata is a lazy notion? What does Mike need to see on the upside to re-invest?
• How does Mike feel about the importance of temporal diversification? Why did Mike increase the cadence of his investing in 2021? Does he regret the increased speed?

3.) The Market 101:

• How does Mike think about the importance of market sizing? If we always underestimate the size of our winners, is this market sizing exercise not destined for failure?
• Why does Mike believe so many over the last few years have poorly sized markets they invested in?
• How does Mike assess market timing risk? What market risk is he willing vs not willing to take?
• What have been some of Mike's biggest mistakes when analyzing markets in the past? How did it change his perspective?

4.) Boards 101:

• How would Mike describe his style of board membership today? How has it changed over time?
• Why does Mike believe that boards at seed are not valuable? When do they become valuable?
• What is the single biggest mistake Mike sees so many young board members make today? What is his biggest advice to young board members?
• How does Mike advise founders on preparing for boards? What does he want to see?
• What are the biggest mistakes founders make when conducting board meetings?

Mike's Favourite Books: Don't Let's Go to the Dogs Tonight: An African Childhood, Days Without End

Mike's Most Recent Investment: Opply

Scott Belsky is an entrepreneur, master of product reviews, author, investor, and currently serves as Adobe's Chief Product Officer and Executive Vice President, Creative Cloud.

Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most game-changing products in society from the iPhone and iPod to more recently founding Nest.

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here.

Kayvon Beykpour is one of the most prominent product leaders of the last decade. For the last 7 years, Kayvon has been at Twitter where he led all of the teams across Product, Engineering, Design, Research and Customer Service & Operations.

Aparna Chennapragada is Chief Product Officer @ Robinhood, the company revolutionising consumer finance with commission-free investing.

1.) What makes a truly great product review?

2.) What are the biggest mistakes that product leaders make when leading product reviews?

3.) Who should be invited to the product review? How does this change with scale? How does this change in a world of remote work and Zoom?

4.) Who should set the agenda for the product review?

5.) How can leaders assign accountability and ensure that the follow-ups from product reviews are executed on?

6.) How can leaders ensure that they do not dominate product reviews with the weight of their words? How can they give designers and devs the space to share their thoughts without being judged?

Daniel Yanisse is the co-founder and CEO of Checkr, a leading HR technology company, currently valued at $5 billion. During the journey, Daniel has raised over $679M for Checkr from some of the best including Accel, Bond, Coatue, GV, Elad Gil and IVP to name a few. Prior to Checkr, Daniel was a software engineer and helped develop prototypes of the Mars Rover for NASA. Daniel has been recognized in Forbes "30 Under 30" and recently Checkr was recognized by Forbes as one of America's best start-up employers.

1.) The Origins of Checkr: The $5BN Company

• How did Daniel come to co-found Checkr? What was the a-ha moment?
• How did Daniel's experience with his prior company impact how he thought about building Checkr?
• What does Daniel know now that he wishes all first-time founders knew when they started?

2.) Hiring 101:

• What are the single biggest hiring mistakes Daniel made in the early days of Checkr?
• How does Daniel structure his interview process for new candidates today? How has it changed?
• How does Daniel test for ego and humility in the interview process?
• How does Daniel approach giving feedback today? How has it changed over time?
• What does Daniel believe is the right way to let someone go? How long does one give a team member who is not performing?

3.) Fundraising 101:

• How does Daniel advise founders going out to raise today in the challenging market conditions?
• What terms should founders optimize for? What terms should they not optimize for?
• What are the single biggest mistakes Daniel sees founders make when raising?
• What does Daniel wish he had done differently with Checkr's raises?
• What was the hardest raise for Checkr? Why was it so hard? What was the outcome?

4.) Going into Enterprise:

• Why does Daniel believe they went into enterprise too soon? What was the result of this?
• How does Daniel advise founders on when is the right time to go into enterprise?
• What changes in both your company and your product when moving to enterprise?

Daniel's Favourite Book: Accelerate: The Science of Lean Software and Devops: Building and Scaling High Performing Technology Organizations