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

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman. If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.
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Now displaying: Category: Investing
Sep 28, 2022

Kipp Bodnar is the Chief Marketing Officer of HubSpot, where he sets HubSpot’s global inbound marketing strategy. Prior to his role as CMO, Kipp served as VP of Marketing at HubSpot, overseeing all demand generation activity worldwide and building out the EMEA and APAC marketing teams. Kipp serves as a marketing advisor for SimplyMeasured, InsightSquared and Guidebook. Kipp is the co-author of “The B2B Social Media Book: Become a Marketing Superstar by Generating Leads with Blogging, LinkedIn, Twitter, Facebook, Email, and More.”

In Today's Episode with Kipp Bodnar We Discuss:

1.) The Journey to CMO @ Hubspot:

  • How Kipp made his way into the world of marketing and came to be CMO @ Hubspot?
  • What does Kipp know now that he wishes all CMOs knew when they started?

2.) Choosing The Channel:

  • How does Kipp advise founders on which channel they should focus on? What is the framework which will tell them which channel is right for them?
  • How many different channels should they try? How focussed should they be? Should they have independent teams for each channel?
  • How do the best founders allocate resources to new channels? How do you know when one is not working and you need to stop? When do you just need to keep going and persisting?
  • What have been some of Kipp's biggest mistakes when entering new channels?

3.) Product Marketing, Brand Marketing and Founders Marketing:

  • How does Kipp advise founders who say that, "social and personal brand is just not for them"?
  • In what two ways does Kipp believe that all businesses are constrained?
  • Does Kipp agree that the state of product marketing has never been worse? What is truly great product marketing to Kipp?
  • How does Kipp distinguish between good and great brand marketing? How has what it takes to be great at brand marketing changed over time?

4.) The Best Marketing People:

  • What are signs of clear 10x performers in marketing?
  • What advice would Kipp give to someone aspiring to be a CMO? What mistakes do 95% make that they should change?
  • How do the best CMOs manage up and manage their team? Why does Kipp compare the role of the CMO to the general manager in NFL teams?
  • Why does Kipp believe the role of the CMO is a lonely one? What are the hardest elements?
  • What framework for learning does Kipp use to learn all new topics? What works? What does not?

Sep 26, 2022

Paul Davison is the Co-Founder and CEO @ Clubhouse, the startup that believes people are at the centre of every moment, providing a platform to talk with friends and meet new friends. To date, Paul has raised over $310M with Clubhouse from a16z, DST, Elad Gil, Naval Ravikant, and many more. Prior to co-founding Clubhouse, Paul was the Founder of Highlight, a location-based consumer social service backed by Benchmark. Before Highlight, Paul actually spent time at Benchmark as an EiR.

In Today's Episode with Paul Davison We Discuss:

1.) Entry into Startups:

  • How Paul came to found Highlight in the early days of consumer social?
  • What elements worked with Highlight that he took with him to Clubhouse? Which elements did not work that he learned from?

2.) Clubhouse: What Worked:

  • What does Paul believe are the primary reasons that Clubhouse grew so fast?
  • What metrics does Paul use to determine true product-market-fit and stickiness?
  • What is good retention on Day 1, Day 7 and Day 30? How important is 12-month retention?

3.) Clubhouse: What Did Not Work:

  • COVID: Does Paul believe that Clubhouse was the COVID antidote we all needed? How sustainable is that if so? What trends make it more sustainable?
  • Live Does Not Work: How does Paul respond to Mike Mignano's comments that "live does not work"? Why does Paul believe that Clubhouse is not a content platform?
  • Quality: Does Paul agree that the quality of live is not as good as the quality of produced content? Is that a problem? If the quality is worse, what is significantly better about live?

4.) The Future of Social:

  • Does Paul agree that we are seeing the disregard of the once hailed social graph in favour of a new era of recommendation media? What does this mean for Clubhouse?
  • With the rise of the likes of BeReal, how does Paul think about the importance of authenticity in the next wave of consumer social?
  • How does Paul forsee Web3 and the next generation of consumer social being interlinked? What will it take for Web3 to break through? What are the core barriers today?
  • Does Paul agree that the best consumer social tools empower creators with Superhuman powers?

5.) Lessons on CEOship:

  • What are Paul's biggest lessons on successful company building?
  • How does Paul manage the criticism and negativity of the press personally?
  • How does Paul maintain the morale internally when the press cycle is so negative?
  • How has Paul adapted himself to gain a thicker skin and not pay as much attention?

Items Mentioned in Today's Episode:

Paul's Favourite Book: Reality Is Not What It Seems: The Journey to Quantum Gravity, Information: A History, a Theory, a Flood

Sep 23, 2022

Julio Vasconcellos is the Founder and Managing Partner @ Atlantico, one of the leading early-stage funds in Latin America. Prior to the world of venture, Julio got his break in the world of startups as Facebook’s first country lead for Brazil. Julio then went on to co-found Peixe Urbano, a company he scaled to over 1,200 employees and $100M+ in revenue. Post the sale of Peixe Urbano, Julio became an EiR @ Benchmark Capital where he met Scott Belsky. Scott and Julio went on to co-found Prefer, a Benchmark backed company transforming the future of work. If that was not enough, Julio has a stellar angel track record with prior investments in the likes of Ipsy and Quinto Andar.

In Today's Episode with Julio Vasconcellos We Discuss:

1.) Entry into Startups:

  • What are 1-2 of Julio's biggest takeaways from being Facebook's first hire in Brazil?
  • What does Julio know now that he wishes he had known at the start of his career in startups?

2.) Lessons from Scaling Peixe Urbano to $100M in Revenue:

  • How does Julio advise founders on when is the right time to launch a second product or market?
  • How does Julio advise founders on the right balance between growth and unit economics?
  • When times are tougher, should founders cut fast or cut slower? What is irreversible?
  • What are the single biggest and worst things to break in hyper-scaling?

3.) Investing: Why Not Enough Play To Win:

  • What is more important, a great market or a great founder?
  • Why do not enough VCs today play to win? If they do not play to win, what do they play to do?
  • Why is greed the number one enemy of venture returns?
  • What are the single biggest investing lessons Julio has learned from Benchmark Founder, Andy Rachleff? How have they impacted his investing mindset?
  • Why does Julio believe you can have a close relationship with founders as an angel and not a VC?
  • How did Julio's approach to investing change with the transition from angel to VC?
  • Does Julio believe that boards really add any value? If so, how?
  • What is Julio's biggest investing hit? How did it change his approach?
  • What is his biggest miss? How did that impact his mindset?

4.) The Future for LATAM:

  • Is Julio as concerned as I am by the removal of growth stage capital from the LATAM ecosytem?
  • Does this mean a higher mortality rate for LATAM companies? How does Julio advise founders?
  • How did COVID adoption of technology in LATAM fundamentally differ to the US?

Sep 21, 2022

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos, which he has led with immense success for the last 9 years. In the last few weeks, David announced his latest move, to join Y Combinator, one of the world's leading accelerators as a Visiting Group Partner. If that was not enough, David also has a stellar angel portfolio with the likes of Rippling, Flexport, Tally, Maven and many more.

In Today's Episode with David Lieb We Discuss:

1.) Entry into Product:

  • How did an idea at business school turn into Bump and ultimately the creation of Google Photos?
  • What are the single biggest mistakes David made with the early Bump product?
  • What does David know now that he wishes he had known at the start of Bump?

2.) Scaling the Team Alongside the Product:

  • What is product-market fit to David? What is it not?
  • What are the single biggest mistakes founders make when they think they have it?
  • What should founders do first and most importantly, when they do have it?
  • Why does David believe individual user data is more important than relying on data?

3.) Product: Art or Science:

  • Why does the description we have for product managers need to change?
  • How does David determine when to act on customer feedback vs stick to the current product plan?
  • What is the right way to do customer discovery? What questions are best to ask? Where do founders make the biggest mistakes in customer discovery?
  • Ultimately, is product more art or science? Is this changing with ever-increasing data?

4.) Product: The Process:

  • How does David conduct product reviews? What are the biggest mistakes founders and product leaders make when managing product reviews?
  • Who is invited? Who sets the agenda? Who determines who is accountable for what?
  • How do product reviews change in a world of Zoom? What is better? What is worse? What can product leaders do to build culture in remote worlds?
  • How can product leaders make everyone feel safe and comfortable to share how they feel, regardless of seniority, in product reviews?

Items Mentioned in Today's Episode:

David's Best Performing Investment: Flexport

Sep 16, 2022

Seba Kanovich is the CEO @ dlocal, the #1 payments leader with a single solution focused on Latin America and other emerging markets. In June 2021, dlocal raised $617M in their NASDAQ IPO listing valuing the company at nearly $9BN. Before their IPO, dlocal raised from some of the best including General Atlantic, Bond Capital, and Oren Zeev to name a few. Prior to dlocal, Seba was CEO @ AstroPay, a leading payment solution provider in Emerging Markets.

In Todays Episode with Seba Kanovich We Discuss:

1.) The Journey to CEO of an $8BN Company:

  • How Seba made his way to the role of CEO of an $8BN company through dinner at his mother-in-law's house?
  • What does Seba know now that he wishes he had known when he first became CEO?

2.) Leadership 101:

  • What does "high performance" in business and leadership mean?
  • How important are velocity and speed of execution in startups? When should one trade speed for quality? Where is the nuance?
  • How does Seba approach prioritization? What framework does he use to determine what to focus on?
  • How does Seba think through effective delegation? How can leaders determine what only they can do?

3.) Leadership: The Challenges and Lessons:

  • What are Seba's biggest insecurities in leadership today? How does he manage them? How have they changed over time?
  • What is the single most painful leadership lesson Seba has learned that he is also pleased to have learned?
  • What gets easier with scale as a leader? What gets harder?
  • In a scaling organization, what is the first thing to break? What can be done to mitigate this?

4.) The Funding and The IPO:

  • Why did dlocal bootstrap for 4 years instead of raise funding? How did that process change their mindset toward capital efficiency? What was good about it? What was bad?
  • What are the single biggest advantages great investors can bring to the table?
  • Why did Seba decide 2021 was the right time to go public?
  • What was the biggest surprise about going public? What is better and what is worse about being a public company?

Items Mentioned in Today's Episode:

Seba's Favourite Book: Steppenwolf by Herman Hesse

Sep 14, 2022

Eleanor Dorfman is a Sales Leader @ Retool, the company that allows you to build internal tools, remarkably fast. Prior to Retool, Eleanor joined Retool when there were only three account executives and has scaled the sales org sales to over 30 AEs, many SEs, and an entire SDR team. Before Retool, Eleanor was at Segment, where she built out the company’s customer success operations team before pivoting to creating an expansion sales team, renewals team, and a new business sales team. Finally, before Segment, Eleanor made her way into startups, starting as an unpaid intern at Clever, just four years later, Eleanor was Head of Customer Success and Solutions Engineering.

In Today's Episode with Eleanor Dorfman We Discuss:

1.) Entry into Sales from Working with the US Education Department:

  • How did Eleanor get her first role as an unpaid intern at Clever?
  • What are 1-2 of her biggest takeaways from her time at Segment?
  • What are the biggest advantages of sales reps having experience in customer success?

2.) The Sales Playbook:

  • How does Eleanor define, "a sales playbook"? When does it need to be created?
  • Does it need to be the founder who creates it or can it be a Head of Sales?
  • Is it possible to run a PLG and enterprise motion from Day 1? How does this change your sales playbook?
  • How does Eleanor advise founders on when is the right time to layer on an enterprise motion, on top of a PLG motion?

3.) Who, What and When: Building the Sales Team

  • Should founders hire a Head of Sales first or sales reps first? If sales reps, should founders always hire sales reps in two's?
  • How does Eleanor structure the hiring process for all new sales team recruits?
  • What are the clearest signals of 10x sales hires? What are red flags in the interview process?
  • How does Eleanor use demo's and case studies to determine technical ability?

4.) The First 30, 60 and 90 Days: The Onboarding:

  • What is the right structure for all new sales hires to be onboarded?
  • Why does Eleanor believe you will always hire your Head of Sales Enablement too late?
  • What are the signs that now is the right time to hire your Head of Sales Enablement?
  • What tools, materials and resources can founders provide to shorten the ramp time for new AEs?
  • What are the single biggest mistakes founders make in the onboarding of new sales reps?

 

Sep 12, 2022

Will Quist is a Partner @ Slow Ventures. Over the last decade, the team at Slow Ventures have invested in the earliest rounds of over 500 companies including Robinhood, NextDoor, Airtable, Solana and many more. As for Will, prior to Slow he spent over 8 years at Industry Ventures and before industry, cut his teeth in the world of finance at Banc of America.

In Todays Episode with Will Quist We Discuss:

1.) Entry into Venture:

  • How Will made his way from 6th generation San Francisco to Partner @ Slow?
  • What are 1-2 of the biggest takeaways from his early 1-1s with Don Valentine?
  • What does Will know now that he wishes he had known when he started in venture with Industry?

2.) WTF Really is Venture Capital?

  • Why does Will believe that 95% of venture capital today is not really venture capital?
  • What is true venture capital in Will's mind?
  • How does Will divide the world of VC into two with; venture classic and new venture?
  • How are they different? How are their return profiles different?

3.) The Questions: Discovering Greatness:

  • Why does Will believe “for the most part, investors across asset classes are just asking the same questions”?
  • What are those questions? What different answers are each looking for?
  • What are the 5 core questions that will needs to understand to determine conviction and accurately price an asset?
  • How does Will think through and analyze the question when meeting founders of; “what needs to come true for this business to become a great business”?

4.) The Future of Venture Capital:

  • How does Will predict the venture capital ecosystem will look in 5 and then 10 years?
  • What are the most concerning traits of the venture ecosystem for Will today?
  • Who will be the winners of the next decade? Who will be the losers?
  • What happens to the crossover funds? What will happen to Tiger?

Sep 7, 2022

Mike Mignano is a Partner @ Lightspeed, one of the most successful venture firms of the last decade with a portfolio including the likes of Snap, Affirm, Epic Games, Mulesoft and more. As for Mike, prior to venture, he was Head of Talk for Spotify where he led the podcast, live, and video businesses for the world’s leading audio streaming platform. Michael came to Spotify through their acquisition of Anchor, a company he co-founded and is credited for democratizing podcasting globally. Mike has also been a prolific angel investor with a portfolio including Cameo, Pipe, Sandbox VR and Stir.

In Today's Episode with Mike Mignano We Discuss:

1.) Exclusive News:

  • What exclusive news does Mike have to share today?
  • What would Mike most like to change about the way founders experience the product of venture capital? How can VCs be better?
  • What is Mike most nervous about in the new role?

2.) The World of Social is Changing Forever:

  • Why does Mike believe there has never been a better time for the next social media giant to be born?
  • Why are the largest social giants leaving behind the social graph?
  • What is recommendation media? Why is it a better business model?
  • How does the shift from social graph to recommendation media change the way large social giants operate and interact today?

3.) Startups: Risers, Fallers and Is There Room For Another Giant?

  • What does Mike believe Clubhouse did well? What was their undoing?
  • Does Mike believe BeReal is defensible? What features make it both sticky and defensible?
  • Will TikTok be a $2 trillion dollar company? Will Meta catch TikTok or have they gone too far ahead?
  • Will OpenSea be able to sustain and make the market for NFTs, despite crypto crashing?
  • Should startups be concerned about large social giants "copying" their features?
  • What does true defensibility look like in consumer social today?

4.) Angel Investing: Hits, Misses and Lessons:

  • From writing over 50 angel checks, what are the single biggest lessons Mike has learned?
  • What has been his biggest hit? How did that change the way he thinks about investing?
  • What has been his biggest miss? In what way did that change how he invests?
  • What advice does Mike give to all angel investors looking to invest today?

Sep 2, 2022

Rene Haas is the CEO @ Arm. The technologies that Arm creates are used in over 230+ Bn devices with everything from sensors to smartphones to servers. In 2016 Softbank made Arm it's largest ever acquisition with a reported price of $32Bn. As for Rene, he was appointed CEO in February 2022 having spent the last 8 years in numerous different roles within the company. Before Arm, Rene was Vice President & General Manager of the Computing Products Business Unit at Nvidia where he enjoyed a very successful 7 years with the team there.

In Today's Episode with Rene Haas We Discuss:

1.) Entry into Tech from Eastman Kodak:

  • How did Rene make his way into the world of technology and innovation?
  • What are 1-2 of the biggest takeaways from his 7 years at Nvidia?
  • How did working with Jensen impact his leadership approach and philosophy?

2.) Decision-Making in Leadership:

  • What is the single biggest mistake leaders make when making decisions today?
  • How does Rene balance the trade-off between speed vs quality of decision?
  • At what point does Rene believe leaders have enough data to make a decision?
  • What does Rene know now that he wishes he had known when he started on decisions?

3.) Scaling the Org and Remaining Nimble:

  • Agile: How does one retain the speed and agility of a startup when one is the size that Arm is today?
  • Ambition: How does Rene as a leader inspire the same level of ambition and vision in his team when Arm is as large as it is?
  • Risk: How does Rene encourage his teams to take large risks when they have so much more to lose?
  • Breakage: What are the first things to break in scaling? What can leaders do to get ahead of them?

4.) Leadership 101:

  • What really is strategy? What is it not? What mistakes do all leaders make when it comes to strategy?
  • How does Rene define "high performance" in leadership? How has his style of leadership changed over time?
  • How does Rene approach vulnerability in leadership? What are the pros and cons?

 

Aug 31, 2022

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health.

In Today's Episode with Annie Pearl We Discuss:

1.) Entry into Product From Consulting:

  • How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor?
  • What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset?
  • What does Annie know now that she wishes she had known when she started in product?

2.) PLG vs Enterprise: What, When, How:

  • Is it possible to do PLG and top-down enterprise strategy together from Day 1?
  • Why does every PLG company eventually have to adopt an enterprise strategy?
  • What are the single biggest challenges companies face when moving to enterprise?
  • How do founders know when is the right time to make this transition?
  • How do founders need to restructure their org to make the transition to enterprise?

3.) Building the Product Bench: Hiring:

  • When is the right time to hire your first product leader? What are the core signals?
  • What are the core character traits needed for a first product leader?
  • How do we specifically structure the interview to test for them?
  • Who do we bring into the interview process from other parts of the org?
  • Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies?

4.) Product Strategy, Reviews and Alignment:

  • How does Annie assess how often product strategy should be reviewed? When should it change?
  • How does Annie approach post-mortems? What is the right way to structure them?
  • How does Annie create alignment between sales and product? Why is this so important?
  • What is the single biggest product mistake Annie has made? What did she learn?

Aug 29, 2022

Logan Bartlett is a Managing Director @ Redpoint, a firm with a portfolio including the likes of Stripe, Nubank, Twilio, Netflix, Snowflake and many more incredible names. As for Logan, at Redpoint he has led investments in the likes of Ramp, Monte Carlo, Cribl, Crossbeam and Acuity MD to name a few. Before joining Redpoint, Logan spent over 5 years with the team at Battery where he made investments in Pendo, Amplitude, Dataiku, Braze and Kustomer.

In Today's Episode with Logan Bartlett We Discuss:

1.) Entry into Venture:

  • How Logan made his way into the world of venture joining Battery Ventures?
  • What are 1-2 of Logan's biggest takeaways from his time with Battery?
  • What does Logan know now that he wishes he had known when he started in venture?

2.) The Venture Landscape Today:

  • Is now really the best time to be investing? How does Logan compare today to prior vintages? How does this differ when comparing consumer to B2B?
  • How does Logan analyze the state of the growth market? Is anyone really doing deals today? If so, what is the discount on price vs last year?
  • How do the public markets impact the later stage financings which have disappeared in the last 3 months? How do the later stage financings impact the early stage?
  • Does Logan agree that "venture has never been less collaborative as it is today"?

3.) The Role of the Venture Investor:

  • Why does Logan believe that VCs have gotten lazy over the last 2 years? Does Logan believe we will see even more GPs at the top retire in the downturn?
  • How does Logan analyse his role as a board member today? How has his style changed over time?
  • What is the single best board Logan is on? Why that one? Who is the best board member Logan works with? What makes this board member so good?
  • How does Logan assess the importance of personal brand in venture today? Why does Logan believe no company should hire PR firms from the early days?

4.) Investing Style and Lessons:

  • What has been Logan's single biggest hit as an investor? How did seeing that impact his mindset?
  • What has been Logan's biggest miss? How did not doing the investment change how he thinks about making new investments today?
  • How does Logan assess his own relationship to price? How has it changed over time?
  • As a growth investor today, how important is ownership? How does this change with stage?

Items Mentioned in Today's Episode:

Logan's Favourite Book: Team of Rivals: The Political Genius of Abraham Lincoln

Logan's Most Recent Investment: AcuityMD

Aug 26, 2022

Whitney Wolfe Herd is the Founder and CEO @ Bumble, changing the way people date, find friends, and the perception of meeting online, for the better. Women make the first move. Over an incredible 6 year journey, Whitney has scaled Bumble to a community of over 100 million across six continents. Bumble has facilitated an incredible 1.8 billion first moves as of 2021 and so many more by now. Prior to founding Bumble, Whitney was the Co-Founder and VP of Marketing @ Tinder.

In Todays Episode with Whitney Wolfe Herd We Discuss:

1.) Founding Bumble:

  • How Whitney made her way into the world of startups with her co-founding Tinder?
  • What happened when Whitney left Tinder in a very public way?
  • How did that and the scrutiny that came with it, impact her? How did she change?

2.) CEOship 101:

  • What does "High Performance" mean to Whitney?
  • What are the biggest benefits and biggest downside of transparency? What are the few things that as a leader, you cannot be transparent about them?
  • What does it mean to truly listen as a leader? What are the biggest mistakes leaders make when it comes to listening?

3.) Risk and Pressure in Leadership:

  • What is the single moment of highest pressure Whitney has been through in the Bumble journey?
  • How does Whitney deal with pressure as a leader today? How has that changed?
  • How does Whitney approach risk as a leader today? What is too risky?
  • How does Whitney think through her own decision-making framework?

4.) Whitney: The Mother and Wife

  • What does Whitney believe makes a truly successful marriage?
  • How does Whitney not lose an inch of performance as a public markets CEO and also be an amazing mother to two children under the age of 2?
  • What does Whitney know now that she wishes she had known when she started Bumble?
  • As a leader and mother, what gets easier with time, what gets harder?

Items Mentioned in Today's Episode with Whitney:

Whitney's Favourite Book: Shantaram

Aug 24, 2022

Over the last 7 years, I have scaled 20VC to 100M+ downloads, and listeners in 117 countries, and all of this with a spend of less than $1,000. Here are 10 of my biggest lessons:

Lesson 1: Persistence: This is a game of who can last the longest.

Lesson 2: Platform Selection: Choose the platform that best aligns to your skills and passion, not the one that is "hottest" at the time.

Lesson 3: Just Start: The biggest reason people fail is because they do not take the first step. The V1 will never be perfect but it will improve. Press publish.

Lesson 4: Consistency: You have to create a habit within your audience. You have to let them know when they should expect your content. This will also creating a forcing function for you to stick to.

Lesson 5: Be Targeted on your Content Topic: Do not be vague. You have to be very specific in the topic you choose. Start very niche. Find your 100 true fans. Expand from there.

Lesson 6: Every Piece of Content is Born Multi-Channel: You do a talk. This is not a single talk. This can be turned into a podcast. Several TikToks. A medium piece. No content is in isolation.

Lesson 7: The Right Ratio Between Creation and Distribution: Do not create content and then press publish and think the work ends there. You have to spend the same amount of time distributing the content as you do creating it.

Lesson 8: Create Champions: In the early days it is all about finding your 100 true fans. DM people that follow you. Make them feel special. They will retain and tell their friends. Create champions.

Lesson 9: Bring People Into the Creation Process: When people feel a part of the creation of content, they will share it actively. Make more people feel part of the creation process.

Lesson 10: Each Channel is Different, Optimise for Them: Different channels require different content types, formats, audio, optimise on a per channel basis.

Aug 22, 2022

Wes Chan is the Co-Founder and Managing Partner at FPV Ventures, a $450M early-stage fund, launched earlier this year. Wes is an investor in five $10B+ "decacorns," his most notable being Canva where he is a member of the board of directors and led the Series A and C rounds. Wes also wrote the first or very early check into Plaid, Flexport, Gusto, Lucid, and RobinHood. Before FPV Wes was a Managing Director at Felicis Ventures and before Felicis Wes founded GV’s seed investing program. If that was not enough, as an operator, Wes co-founded Google Analytics and Google Voice and holds 18 US patents for his work in creating Google AdWords.

In Today's Episode with Wes Chan

1.) From Founding Google Analytics to Venture:

  • How did Wes make his way from founding Google Voice and Google Analytics to starting GV's seed investing program?
  • What are 1-2 of the single biggest product takeaways from working closely with Larry and Sergey @ Google?
  • How did Wes make his way from Google to Felicis and scaling the firm with Aydin Senkut?

2.) Market vs Founder: Why Market Sizing is BS:

  • Why does Wes believe that the market always wins over the founder?
  • That said, what does Wes mean when he says "the best founders have 100 year plans?"
  • How does Wes question and analyse 100 year plans? What makes the best? What makes the worst?
  • Why does Wes not do market sizing? Why does Wes not do outcome scenario planning?
  • What does Wes believe is the biggest fallacy of outcome scenario planning?

3.) The Venture Landscape:

  • Does Wes believe that now is really the best time to be investing?
  • Why does Wes believe there are some treacherous deals being done now? What are the signs that these deals are challenging?
  • What advice does Wes give founders fundraising in these markets?
  • What does Wes believe are elements that traditional VCs decide to do, which prevents founders from choosing to work with them?
  • Does Wes believe VCs on board truly provide value? If so, which ones and why them?

4.) FPV: Firm Building and Portfolio Construction:

  • With the new $450M fund, what is the portfolio construction that Wes chose?
  • Why does Wes prefer to have more lines in the portfolio than a concentrated portfolio?
  • Does Wes believe you can increase your ownership in your best companies over time?
  • How does Wes think about capital concentration on a per company basis?
  • What have been Wes' biggest lessons from his biggest hits and misses?

Items Mentioned in Todays Episode:

Wes' Favourite Book: Liar's Poker

Aug 17, 2022

Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California.

In Today's Episode with Jordan Van Horn We Discuss:

1.) Entry into the World of Sales:

  • How did Jordan make his way into the world of sales first with a vineyard?
  • What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset?
  • What does Jordan know now that he wishes he had known when he entered sales?

2.) The Sales Playbook:

  • How does Jordan define "the sales playbook"? What is it not?
  • What five core things should the sales playbook help you accomplish?
  • Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales?
  • How does Jordan advise founders on three signals that now is the right time to bring in a sales hire?
  • How does Jordan advise founders on whether the first sales hire should be a rep or a leader?

3.) The Secrets to Pricing and Discounting:

  • Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for?
  • When does price discipline become important in a company journey? What are the dangers of not having price discipline?
  • What two tools do sales leaders have to use in order to create urgency in a deal closing process?
  • How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it?

4.) The Hiring Process:

  • How does Jordan structure the hiring process for all new sales hires?
  • What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers?
  • Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for?
  • Does Jordan use case studies with candidates? What makes the best? What makes the worst?

5.) The Onboarding:

  • What is the ideal onboarding process for new sales reps?
  • What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready?
  • What are some early signs that a new hire is not working out? How do we measure their impact?
  • For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long?

Aug 15, 2022

Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired. If that was not enough, Sheel is also a master at measuring the width of swimming pools and making cameo appearances in music videos with Justin Bieber.

In Todays Episode with Sheel Mohnot We Discuss:

1.) Entry into Venture:

  • How Sheel made his way into the world of venture having founded 2 fintech companies?
  • Why did no LPs give Sheel money in the early 500 Fintech days? What were some of his biggest lessons from investing in 100s of companies with 500 Fintech?
  • How did BTV with Jake come together most recently? What are the biggest differences to Sheel of being a fund manager vs being an investor?

2.) The Power Law:

  • How does Sheel define "the power law" in venture capital? What multiple of return would be power law status?
  • Given the size of outcome available with these power law returns, how does Sheel approach portfolio construction? Would it not be best to invest in 100s of companies?
  • Who does Sheel believe has done the indexing approach best? Why?

3.) Venture Capital has Never Been Less Collaborative:

  • Why does Sheel disagree with Harry that venture capital has never been less collaborative?
  • Why now, for the first time, are large multi-stage funds taking single-digit ownership?
  • Does Sheel agree with Harry it is moronic to have "guaranteed pro-rata"? How does Sheel approach re-investment decision-making? When does he pay up vs not?

4.) The Biggest Wins and Misses:

  • What have been Sheel's biggest wins from a cashback and a multiple perspective?
  • How did Sheel miss the chance to invest in both Robinhood and Chime early on? What did he not see? How would he have thought differently with the benefit of hindsight?
  • How have Sheel's biggest hits and misses impacted how he invests today?

5.) Emerging and Frontier Markets:

  • Does Sheel share Harry's concern for the removal of capital from emerging markets?
  • Why does Sheel believe that India, South East Asia and LATAM will be fine?
  • Why does Sheel believe Pakistan and Africa are most in trouble?
  • What advice does Sheel give to his emerging markets founders today?

Items Mentioned in Today's Episode:

Sheel's Favourite Book: Enders Game

Aug 12, 2022

Marcelo Claure is an entrepreneur and investor who has founded and led some of the world’s most iconic businesses. He is currently the Chairman & CEO of Claure Capital, a newly founded multi-billion-dollar global investment firm. Before this, Marcelo was COO @ Softbank Group, the world’s largest technology investment company.

Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more.

Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade.

David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more.

Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few.

Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital.

Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ’s total value.

Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN.

Nick Shalek is a General Partner @ Ribbit Capital, specializing in fintech they are one of the most successful venture firms of the last decade with a portfolio including Robinhood, Coinbase, Revolut, Nubank and more.

Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more.

Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives.

Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures. Their portfolio includes SpaceX, Wish, Anduril, Flexport, and WorkRise (formerly Rigup) to name a few.

David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora.

In Today's Episode We Discuss Price Sensitivity:

1.) How do you assess your relationship to price and price sensitivity?

2.) When is the time to pay up and have less price discipline?

3.) When should we remain disciplined and not pay up for a deal and walk away because of price?

4.) Of the deals you have paid up for, did their growth rate justify the high entry price?

5.) Knowing all you know now on price, how do you advise younger investors today?

Aug 10, 2022

Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of 'The Hustle.' He is also an advisor and investor in early-stage companies.

In Today's Episode with Kieran Flanagan We Discuss:

1.) Entry into Growth and Marketing:

  • How did Kieran make his way into the world of growth and marketing?
  • What has been 1-2 of Kieran's biggest lessons from seeing firsthand the hyper-scaling of Hubspot?
  • On reflection, how would Kieran summarise both Hubspot's community building attempts and also their product messaging?

2.) Why You Need Growth Hires Pre Product Market Fit:

  • What does "growth" mean to Kieran? Where do so many get it wrong?
  • Why does Kieran believe that you should have a growth team/people before product market fit? What specifically do they do and work on during this stage?
  • Pre PMF, what is the core metric that all startups should focus on? How does it change with time?

3.) Building Your Growth Team:

  • What does Kieran believe are the 3 key stages to hiring for growth?
  • How should founders determine whether to have external standalone growth teams or integrate them into existing functions?
  • What are the single biggest mistakes founders make when hiring for growth?

4.) The Future is Content:

  • Why does Kieran believe every great tech brand will have to become a media brand?
  • Why is Elon Musk an example of the perfect brand? What has he done right?
  • Why does Kieran say that data is the best and worst thing that has happened to marketing?

5.) WTF Really is Community:

  • How does Kieran define "community"? What is it? What is it not?
  • What makes the best communities? Why do some work and others not?
  • Should every company have a community approach? Who does it make sense for?
  • Have Hubspot done a good job at community building? On reflection, is there anything that Kieran would have done differently?

Aug 8, 2022

Mo Koyfman is the Founder and General Partner @ Shine Capital, who announced earlier this year Shine II, a $200M early-stage fund, and Shine Opportunities I, a $100M vehicle. Prior to founding Shine, Mo was the Managing Member @ Moko Brands where he made angel investments in Coinbase, Polychain, Harry's to name a few. Before Moko, Mo spent over 7 years as a General Partner @ Spark Capital where he made investments in Plaid, Warby Parker, Skillshare and Hivemapper, to name a few. Finally prior to Spark, Mo spent over 5 years at IAC where he oversaw group of companies that included Connected Ventures, parent of Vimeo, CollegeHumor & BustedTees.

In Today's Episode with Mo Koyfman:

1.) From Entrepreneurial Parents to IAC, Spark Capital and Founding Shine:

  • How did Mo make his way into the world of venture having worked with Dara Khros, Barry Diller and Jeremy Liew?
  • What were some of the biggest takeaways from his time with Barry Diller and IAC?
  • How did Mo's time at Spark impact his investing mindset? What did he learn that he took with him to founding Shine?

2.) Investment Firm vs Investment Partnership:

  • What are the biggest differences between investment firms and investment partnerships?
  • What are the biggest risks founders are taking when they take money from investment firms?
  • Mo has very strong beliefs, how does he manage and inspire debates within his firm without shutting down or intimidating younger, less experienced team members?
  • What does Mo mean when he says, "firms are great but partners matter".

3.) How To Win in Venture:

  • Why does Mo always believe that small funds outperform large funds?
  • What have been some of Mo's biggest lessons from Fred Wilson on fund strategy and sizing?
  • How much of an emphasis does Mo place on the importance of ownership?
  • Why does Mo believe the way to win in venture is to be collaborative?
  • Why does Mo believe in the macro conditions we are entering, the landscape is about to become a lot more collaborative?
  • Why does Mo believe any firm that says they will always do their pro rata is lying?

4.) The Lessons: Success and Failure:

  • What are some of Mo's biggest lessons from his biggest wins, like Plaid at seed?
  • That said, why does Mo believe it is so dangerous to try and learn lessons from the wins?
  • What failures have been most impactful to Mo? What did he take away from them?
  • Why does Mo believe that making great burgers is like building great companies?

Items Mentioned in Today's Episode:

Mo's Favourite Book: Portnoy's Complaint by Philip Roth

Aug 5, 2022

Sameer Shariff is the Co-Founder and CEO @ Cambly, the company that allows you to become fluent faster through one-on-one video chat lessons with native English tutors. To date, Sameer has raised over $60M with Cambly from the best including Jeremy Levine @ Bessemer, Sarah Tavel @ Benchmark, Monashees, YC and more. Prior to founding Cambly, Sameer spent close to 5 years at Google on the Search Quality team and became the Tech Lead of the Search experiments team helping make experimentation a core part of the launch process.

In Today's Episode with Sameer Sharif We Discuss:

1.) Entry into Startups and Co-Founding Cambly:

  • How did Sameer make his way into the world of tech with his joining Google straight out of college?
  • What were the 1-2 biggest takeaways from his time at Google? How did it shape his mindset?
  • What was the a-ha moment for Sameer with Cambly?

2.) The Trials and Tribulations of Leadership:

  • What does "high performance" mean to Sameer in business? How has it changed over time?
  • What are the first things to break in a scaling company?
  • How do the best companies retain speed and agility with scale?
  • What are the single biggest hiring mistakes Sameer has made? What did he learn?

3.) The Fundraise that Led to Cash Flow Positive:

  • Why does Sameer think it was so hard to fundraise for Cambly in the early days?
  • When they failed to raise their Series A, what 3-4 core decisions did they make to get Cambly to cash flow positive as fast as possible?
  • How did Sameer communicate their failed fundraising to the team? How did he do this in a way that rallied the troops and did not worry or scare them?
  • What was the tipping point for fundraising to become much much easier for the company?
  • Given they have not touched any of their Series A or Series B funds, how does Sameer think about the balance of growth vs profitability?

4.) Marketplace Dynamics 101:

  • How did Cambly acquire the first 100 customers on the demand side?
  • What is the most challenging dynamic of Cambly; demand or supply side?
  • Where does Sameer see most marketplace founders make the biggest mistakes?
  • What does Sameer know now on the intricacies of marketplace dynamics that he wishes he had known at the beginning?

Items Mentioned In Today's Episode with Sameer Shariff:

Sameer's Favourite Book: The Most Human Human: What Artificial Intelligence Teaches Us about Being Alive

Aug 3, 2022

Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped define and grow the Product Management function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter and prior to Twitter spent over 6 years as a Group Product Manager @ Google. Today Shreyas has invested and advises some of the best including advising Airtable, Kalshi, Lendflow, to name a few.

In Today's Episode with Shreyas Doshi:

1.) Entry into Product:

  • How did Shreyas make his way into the world of product and product management?
  • Why did Shreyas decide not to do business school when it was the conventional route for everyone going into product management?
  • What were some of Shreyas' biggest takeaways from his time at Stripe and Google? How did they impact his product mind today?

2.) Product Management 101:

  • How does Shreyas define product management today? How do many confuse it?
  • How does Shreyas define product success today? What is the single biggest mistake Shreyas sees founders make when determining the success/PMF of their product?
  • Does Shreyas believe that great product management is science or art? Data or intuition? When should you listen to customers? When should you not?

3.) Metrics 101 & How To Use Them:

  • What is the single biggest mistake Shreyas sees founders make when it comes to selecting their North Star metric?
  • How should founders think about input vs output metrics? What is the difference between the two?
  • What are the 6 types of metrics that all founders and product teams need to focus on? How does their importance change over time?
  • How should the responsibility for these metrics be split between different people and teams?

4.) Three Types of Product Leader:

  • What are the three different types of product leaders?
  • The Craftsperson: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company?
  • The Operator: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company?
  • The Visionary: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company?

Aug 1, 2022

Kirsten Green is the Founder and Managing Partner @ Forerunner Ventures, one of the leading firms of the last decade investing at the intersection of innovation and culture. As a founder, Kirsten has led efforts to raise over $2B+ from leading institutional investors and invest in more than 100 companies. She currently serves as a board member at Glossier, Ritual, Faire, Hims & Hers, and Curated, to name a few. She has also invested in other smash hits including Chime, Jet, Warby Parker, Hotel Tonight and many more. Due to her immense success, Kirsten has been honored in Time’s 100 Most Influential People and named a Top 20 Venture Capitalists by The New York Times in 2018 & 2017. Prior to Forerunner, Kirsten was an equity research analyst and investor at Banc of America Securities.

In Today's Episode with Kirsten Green We Discuss:

1.) Entry in Venture at 40 and Founding Forerunner:

  • How did Kirsten make her way into VC at 40 with the founding of Forerunner having never had a role in VC before?
  • What did everyone tell Kirsten when she was looking to break into venture? What did she tell herself when she heard this?
  • What does Kirsten believe she is running from? What does she believe she is running toward?

2.) Fund Management and Leadership:

  • How does Kirsten define high-performance today? What are the nuances of high performance in fund management?
  • How would Kirsten describe her leadership style today? How has it changed over time?
  • What have been some of Kirsten's biggest lessons in terms of what it takes to retain quality with scaling AUM and teams?
  • What have been Kirsten's biggest lessons when it comes to giving hard feedback with kindness?

3.) The Venture Landscape Today and Forerunner's Position:

  • Why does Kirsten believe the venture landscape is more dynamic today than ever?
  • Does Kirsten agree with the statement that venture is less collaborative than ever?
  • Why did Kirsten and Forerunner seem to amend strategy and move into B2B?
  • Why does Kirsten disagree with the delineation between B2C and B2B?

4.) Parenting, Relationships and Life:

  • What have been Kirsten's biggest lessons since becoming a parent? How has it impacted her mindset?
  • Does Kirsten agree that relationships attract from sheer input on work? How does Kirsten separate relationships into two kinds of relationships?
  • What does success in marriage mean for Kirsten? How has she seen that in her own marriage?

Jul 29, 2022

Jim Lanzone is the CEO @ Yahoo, a company that today reaches nearly 900 million people around the world and is the third largest property on the Internet. Prior to Yahoo, Tim was the CEO of Tinder, the world’s most popular app for meeting new people, downloaded by more than 400 million people. Before Tinder, Jim spent a decade as President and CEO of CBS Interactive, a top 10 global Internet company with brands ranging from CBS All Access to CNET. He joined CBS Interactive in 2011 when CBS Corporation purchased Clicker Media, where he was founder and CEO. Before founding Clicker, Jim served as CEO of Ask.com (formerly Ask Jeeves).

In Today's Episode with Jim Lanzone

1.) Jim's Entry into the World of Startups:

  • How did Jim go from law school to founding his first tech startup in the dot com boom?
  • How did seeing the crash and the first company going bust, shape Jim's perspectives on great leadership?
  • What does Jim know now that he wishes he had known when he started way back in 1999?

2.) Leadership 101:

  • How does Jim define "high performance" in business today?
  • What are the 4 things Jim always looks for when hiring new people?
  • Why does Jim believe the standard interview process and questions are broken? How does he do it differently? What are his biggest lessons on how to hire effectively?
  • How does Jim know when to let someone go? How long do you give under-performers?

3.) Crashes and Turnarounds:

  • Jim has seen three crashes as a CEO, what are Jim's biggest lessons from 3 prior crashes?
  • How does Jim advise founders to be acting today? What should they focus on?
  • How can leaders maintain morale and optimism in the face of tough macro times?
  • How does Jim advise founders to communicate both with their investors and board when it comes to reduced performance in harder times?

4.) The Yahoo Turnaround:

  • What does Jim believe the 1-2 core things Yahoo needs to fix is? Why are they priorities?
  • How does Jim approach turning round the Yahoo brand? How does he plan to make it attractive?
  • What is the biggest misnomer that people have about Yahoo today?
  • How does Jim think about running a portfolio approach with Yahoo moving forward?
  • How has Jim changed the org structure and management of Yahoo most significantly?

Items Mentioned in Today's Episode:

Jim's Favourite Book: Team of Rivals: The Political Genius of Abraham Lincoln

Jul 27, 2022

Today we deconstruct the canonical question in early-stage sales. Does the founder need to create the sales playbook? Then secondly, if not, should the first sales hires be reps or a sales leader? Today we are joined by 7 of the best sales leaders to share their thoughts.

Jordan Van Horn is a Revenue Leader @ Montecarlo. Previously Jordan spent 4 years with Segment and before that spent another 4 years at Dropbox.

Oliver Jay (OJ) most recently spent 6 years at Asana where he was hired as the company’s first revenue leader. Before Asana, OJ spent 4 years at Dropbox where he scaled the sales team from 0 to 50 while tripling ARR.

Dannie Herzberg is a Partner @ Sequoia Capital and previously spent 4 years at Slack as their Head of Enterprise Sales. Before Slack, Dannie spent 5 years at Hubspot building sales, opening an SF office, and then joining product to launch CRM & platform.

Zhenya Loginov is the CRO @ Miro, where he runs the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas.

Kyle Parrish is VP Sales @ Figma, where he has scaled the sales team from 0 to over 100 people in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, where he scaled the Austin, Texas office from 3 to over 80 people.

Sam Taylor is the VP of Sales and Customer Success @ Loom, at Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist. 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.

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM.

Mitch Tarica is Head of North America Sales at Zoom Video Communications. Before Zoom, Mitch spent over 5 years at RingCentral and before RingCentral, Mitch was at Oracle for over 7 years in numerous different sales roles.

In Today's Discussion on Sales Playbooks We Learn:

1.) What is the right definition for a "sales playbook"?

2.) When is the right time to change your "sales playbook"?

3.) What are the biggest mistakes or misnomers made around the "sales playbook"?

4.) Should the founder be the one to create the first sales playbook or can it be a sales leader?

5.) When is the right time for founders to hire their first sales leaders?

6.) For the first sales hire, should founders hire sales reps or a sales leader?

7.) When should you hire a rep vs a sales leader? What are the nuances?

Jul 25, 2022

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.

In Today's Episode with Tony Fadell: New York Times' 36 Questions of Love

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?

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