20VC: How Founders Should Think Through Distribution and Customer Acquisition Today, The Challenges of the Digital Advertising Duopoly Currently & How To Structure Company Post Mortems Effectively with Gabriel Weinberg, Founder & CEO @ DuckDuckGo

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Gabriel Weinberg is the Founder & CEO @ DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. Over the last 12 years, Gabe has scaled DuckDuckGo to doing 1.6Bn private searches every month, a team of 83 full time fully remote employees, raising funding from some of the best in the business; USV and most importantly, being a profitable company. If that was not enough, Gabe has also written two phenomenal books, Traction and Super Thinking. 

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In Today’s Episode You Will Learn:

1.) How Gabriel made his way into the world of startups and came to found one of today’s leading search engines and privacy companies in DuckDuckGo?

2.) Gabriel decided to raise from USV 4 years into the life of DDG, why did he believe that was the right time? Why does Gabe believe that DDG never needed any primary capital? How does Gabe advise founders to think when it comes to chasing profitability early? How does Gabe view the relationship between growth and capital? Are they in conflict or aligned? What does Gabe make of the many $100M rounds getting done today?

3.) How does Gabe feel about the lack of free and open distribution today? How does Gabe strategise when it comes to channel diversification? What is the right level of marketing channel diversification to have? How do you know when to really double down on one that is working? How should founders be thinking about channel saturation rates? What have been Gabes biggest lessons on payback period over the last 12 years with DDG?

4.) How does Gabe feel about the digital advertising duopoly on the internet between Facebook and Google? Why does Gabe argue that this duo of incumbents are so much more powerful than any other prior generation of incumbents? How does Gabe think about strategies to reduce their data monopolies?

5.) DDG is 83 people and fully remote, what have been Gabe’s biggest lessons on what it takes to run a fully-remote team from Day 1? What mistakes did they make? WHat would Gabe advise founders contemplating the fully remote strategy? Why does Gabe have nor formal hierarchy or org chart internally at DDG? Why is this so important for culture and employee morale?

Items Mentioned In Today’s Show:

Gabe’s Fave Book: The Advantage: Why Organizational Health Trumps Everything Else In Business

As always you can follow HarryThe Twenty Minute VC and Gabe on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

20VC: Lessons from 150 Angel Investments into the likes of Carta, Gusto, Airtable and Superhuman, Creating Algorithms and Models For Investing At Seed & Why Younger Investors Have An Advantage When It Comes To Finding Deals Early with Jude Gomila, Angel Investor & Founder @ Golden

Jude Gomila @ Golden

Jude Gomila is the Founder & CEO @ Golden, creating the world’s first self-constructing knowledge database built by artificial and human intelligence. To date, Jude has raised from some of the best in the business including Founders Fund, a16z, SV Angel and one of my dearest friends, Josh Buckley. Jude is also a prolific angel having invested in over 150 companies including Carta, Airtable, Superhuman, Gusto, Linear and many more incredible companies. Prior to Golden, Jude started Heyzap (now used by 100,000 mobile apps) alongside former guest Immad, now Founder of Mercury.

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In Today’s Episode You Will Learn:

1.) How Jude made his way into the world of tech and Silicon Valley having been born and raised in Harrow, London? How did he then make his way into the world of investing?

2.) What models should investors and founders have common ground on? Where are founders and investors often misaligned? What does Jude mean when he says he uses “algorithms for investing”? How are these algorithms structured? What is within them? How can/should people build their own?

3.) Why does Jude very much disagree with spray and pray to be the dominant model to make money at seed? How does Jude think about portfolio construction having now made 180 investments? How has Jude’s approach and attitude to ownership changed over time?

4.) Does Jude agree with Semil Shah that founders are voting with their feet and taking multi-stage money at seed today? How does Jude evaluate the approach of multi-stage funds back into seed? How does Jude think about VC value add? Where does he believe they really can add value? Where do people think they do but they actually do not?

5.) How does Jude foresee the future of the early-stage market? Will we see a generation of old school venture firms die out? Why does Jude believe younger investors have a higher chance of finding and winning the next best deal? How does Jude believe the angel ecosystem will shake out? Will we fundamentally see the unbundling of capital?

Items Mentioned In Today’s Show:

Jude’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid

Jude’s Most Recent Investment: Linear

As always you can follow HarryThe Twenty Minute VC and Jude on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Why You Never Want To Fight A Fair Fit For Distribution, Why No Great Company Is Built with 1 Product and When To Release Your Second & What Founders Can Do To Extract The Most From Their Cap Table with Shoaib Makani, Founder & CEO @ KeepTruckin

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Shoaib Makani is the Co-Founder & CEO @ KeepTruckin, the modern fleet management platform building solutions that make drivers and fleets safer, smarter, and more efficient. To date, Shoaib has raised over $229M from some of the world’s leading investors including Index, GV, Greenoaks, IVP & Scale Venture Partners. Pre-founding KeepTruckin, Shoaib was an investor @ Khosla Ventures where he led investments in Instacart, Everlane and Indiegogo to name a few. Before venture with Khosla, Shoaib was on the operations side enjoying roles at both Google and Admob.

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In Today’s Episode You Will Learn:

1.) How Shoaib made his way from the very comfortable world of venture to changing the way trucking fleets are managed today with KeepTruckin? How does Shoaib analyse and assess his own attitude to risk today?

2.) How has Shoaib seen himself change and evolve as a leader over the last few years? How did his time investing impact how he approaches the role of CEO? How does Shoaib think about appropriate market sizing today? What advice does he give to founders on this? What is a reasonable market penetration to assume if successful?

3.) What advice would Shoaib give founders when it comes to successful board management? How does Shoaib ensure investors have the right context at the right time to provide advice? What does that information flow to investors look like? How does Shoaib determine between the advice to accept vs what to reject?

4.) Shoaib thought about distribution and customer acquisition long before he launched the product, why? What did this thought process conclude with? Does Shoaib believe you have to own your own lines of distribution to succeed? How does Shoaib feel when it comes to current CAC’s on incumbent platforms?

4.) As a founder, what does Shoaib say is his biggest mistake made in the KeepTrickin journey? How does Shoaib think about what it takes to acquire the very best talent? How does Shoaib advise founders work with recruiters? What can they do to really get the most out of them? When can this function be brought in house?

Items Mentioned In Today’s Show:

Shoaib’s Fave Book: Presidents of War

As always you can follow HarryThe Twenty Minute VC and Shoaib on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Breaking News: Meet First Round Capital’s Newest Partner, How To Approach Generational Transition as a Venture Firm & The Dangers of Attribution In Venture

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Todd Jackson is First Round Capital‘s newest Partner (announced today) having spent the last 2 years as a Founder-in-Residence working with the FRC portfolio. Prior to his time in venture, Todd spent close to 3 years at Dropbox as VP Product & Design. Before that he was with Twitter as Director of Product Management, following his startup, Cover, being acquired by Twitter in 2014. Before founding Cover, Todd was a Product Manager @ Facebook where he helped lead major redesign of Newsfeed. Finally, Todd started his career at Google as a Product Lead taking Gmail from 0 to 200m users in 4 years.

Todd is joined today by his Partner @ First Round, Phin Barnes. Phin also writes the most fantastic blog, sneakerheadVC, that really is a must-read.

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In Today’s Episode You Will Learn:

1.) Phin, what is the exclusive news you would like to break on the show today? Todd, taking one step back, how did you make your way to this stage, what was your entry into technology and how did you come to be a Partner @ First Round Capital today? What were Todd’s biggest takeaways from working on some of the most transformative social products in Gmail, Twitter, Newsfeed @ Facebook and Dropbox?

2.) What advice does Phin have for Todd when it comes to entering a venture partnership? Where do many people go wrong in their first year in venture? What should Todd be optimising for in the partnership? In terms of measurement, how does one measure success of the first year of work as a Partner?

3.) Todd, making the move from angel to institutional VC is a mindset shift, how does Todd think his investment mentality will be impacted by the shift from angel to institutional VC? Having raised funding as a founder, what type of founder experience and investor does Todd want to be and bring?

4.) Phin, it has been a long time since FRC added a Partner, walk me through the recent changes at the top of FRC? What are the most important qualities for First Round when adding a Partner? What are the biggest tips to doing generational transition well? Where do many firms go wrong in generational transition?

Items Mentioned In Today’s Show:

Todd’s Fave Book: Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve JobsTrillion Dollar Coach: The Leadership Handbook of Silicon Valley’s Bill Campbell

Todd’s Most Recent Investment: Papaya Payments, Snackpass

As always you can follow HarryThe Twenty Minute VC and Todd on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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20VC: Alexa Von Tobel on Raising NYC’s Largest Ever Female Led Fund, Portfolio Construction, Compression of Fundraising Timelines, Reserves Management & Personal Branding in Venture

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Alexa Von Tobel is the Founder & Managing Partner @ Inspired Capital, announced in 2019 as the largest ever female-led VC fund based in NYC. Prior to co-founding Inspired, Alexa founded LearnVest where she enjoyed an incredible 11-year journey culminating in their $250M exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times Bestseller “Financially Fearless” and is an inaugural member of the Presidential Ambassadors for Global Entrepreneurship for the White House.

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In Today’s Episode You Will Learn:

1.) How Alexa made her way into the world of startups with the founding of LearnVest? How did that experience running LearnVest lead to her founding NYC’s largest-ever female-led VC fund in the form of Inspired?

2.) How does Alexa think about portfolio construction with the new $200M fund? What does she mean when she says they have segmented it into 3 distinct and separate buckets? How much is in each bucket? How does Alexa think about reserves and re-investment decision making? What is the process here?

3.) As a former entrepreneur, how does Alexa think about those moments when the VC and the Founder are no longer aligned? What are those moments? How does Alexa approach the aspect of saying no to founders? What is the right way? How does Alexa feel about the compression in fundraising timelines? How does Alexa meet founders before they raise their round?

4.) Why does Alexa believe that capital is no longer the differentiator? How does Alexa think about personal brand in venture today? Where does Alexa believe are the most crucial times for reputation building? How does Alexa approach time allocation across the portfolio? What is the correlation between decision-making and reputation?

Items Mentioned In Today’s Show:

Alexa’s Fave Book: The Power of Moments: Why Certain Experiences Have Extraordinary Impact

Alexa’s Most Recent Investment: Snackpass

As always you can follow HarryThe Twenty Minute VC and Alexa on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: Moxxie Ventures’ Katie Stanton on What It Takes To Raise A First Time Fund As A Solo GP, The Entrance of Multi-Stage Funds Into Seed Rounds and The Inverse Relationship of Those That Fund Diverse Managers and Those That Say They Do

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Katie Stanton is the Founder and General Partner of Moxxie Ventures, investing in founders who make life and work better. Prior to Moxxie, Katie was a Founding Partner of #angels and has the most incredible angel portfolio including Airtable, Carta, Cameo, Coinbase and Modern Fertility to name a few. Katie also served in numerous executive operating roles at TwitterGoogleYahoo, and Color and also served in the (Obama) White House and State Department. If that was not enough, Katie is also on the board of Vivendi and previously sat on the board of Time Inc.

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In Today’s Episode You Will Learn:

1.) How Katie made her way into the world of tech with Yahoo? How did that translate into her investing in Lowercase Fund I? How did the angel investing lead to founding Moxxie? How has Katie found her investment mindset has changed moving from angel to VC?

2.) How did Katie find the fundraise for Moxxie? How many LPs did Katie meet and how did she structure the process? What does Katie think she did well in the fundraise? What would she look to improve or change when raising for Fund II? What advice was Katie given in the process by Semil Shah which really changed her thinking? What advice would Katie give to other emerging managers raising today?

3.) Does Katie agree with Semil Shah that “founders are voting with their feet in taking multi-stage money at seed”? What advice does Katie give to founders who do have these offers from multi-stage funds at seed? How does Katie assess these later stage funds moving earlier? How should smaller micro-managers respond to this?

4.) How does Katie think about portfolio construction today with Moxxie? What are the hard rules that mean Katie is willing to walk away from a deal? How does Katie think about and assess her own price sensitivity? In terms of decision-making, what support system has Katie built around herself to enhance her decision-making process?

5.) How does Katie advice founders when it comes to selecting their VC? What are the most common ways founders look for and need to help with? How does Katie think about party rounds? When are they good? When are they not? Why does Katie believe so much of the power has shifted to the hands of the founders?

Items Mentioned In Today’s Show:

Katie’s Fave Book: Becoming by Michelle Obama, Angel by Jason Calacanis

Katie’s Most Recent Investment: ethel’s club

As always you can follow HarryThe Twenty Minute VC and Katie on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC: The Most Successful Companies Are Not Where Employees Work The Most, How To Know When To Promote From Below Or Bring in External Candidates & Why It Is A Unique Advantage To Be Building A Company Outside A Tech Hub with Rick Nucci, Founder & CEO @ Guru

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Rick Nucci is the Co-Founder & CEO @ Guru, the knowledge management platform that delivers everything you need so you can spend less time searching and more time doing. To date, Rick has raised over $38m with Guru from some of the best in the business including Thrive, Emergence Capital, Firstmark, Slack and Salesforce. Prior to Guru, Rick was the Founder of Boomi, which defined and led a new segment as the first-ever cloud integration platform-as-a-service. Boomi was ultimately acquired by Dell where Rick went on to grow the organisation into the industry leader it is today.

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In Today’s Episode You Will Learn:

1.) How Rick made his way into the world of startups originally and how he came to change the way we think about knowledge management with his founding of Guru?

2.) How would Rick describe his leadership style today? How has he seen his style change over the years? What have been those learnings and the inflexion points causing them? Does Rick believe can be learned as a leader? What does he recommend to founders wanting to become more empathetic?

3.) Culture is a fluffy and overused term, what does it mean to Rick? What has Rick done to purposefully build a very specific culture that he wanted to create? What specific initiatives have worked well? What have not worked so well? How does Rick think about culture maintenance with scale? What are the challenges with scaling culture?

4.) How does Rick think about the interview process when adding to the team at Guru? How do they literally structure it? What does their culture interview encompass? How heavily is it weighted? What specific questions do they ask and responses they look for? If it does not work out, what have been Rick’s biggest lessons on letting people go?

5.) Rick is based in Philadelphia, often people say if you are not in a tech hub it is not possible to get the best talent, does Rick agree with this? In what roles does it make sense to hire from a tech hub for? What are the advantages of hiring outside of a hub? Fundraising wise, does Rick believe you have to have a presence in a core hub to raise from Tier 1 VCs?

Items Mentioned In Today’s Show:

Rick’s Fave Book: The 9 Types of Leadership: Mastering the Art of People in the 21st Century Workplace

As always you can follow HarryThe Twenty Minute VC and Rick on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

 

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