20VC: How To Solve The Chicken and Egg Problem in Marketplaces? How Important Is Differentiated Supply? How To Prevent Leakage? How to Create Marketplace Defensibility and more with Alyssa Ravasio, Founder & CEO @ Hipcamp

Alyssa Ravasio is the Founder & CEO @ Hipcamp, the startup that allows you to book unique camping experiences on over 300,000 campsites, cabins, RV parks, public parks and more. To date, Alyssa has raised over $41M in funding from some of the best in the business including Benchmark, a16z, Brad Feld, Dave Morin, Sam Shank @ Hotel Tonight and more. Prior to founding Hipcamp, Alyssa enjoyed numerous diverse roles including being Director of Sales & Marketing @ Revel Systems to working on International Information and Communication Policy in the US State Department.

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In Today’s Episode You Will Learn:

1.) How Alyssa made her way from the US State Department to founding the game-changer of camping experiences in the form of Hipcamp?

2.) How did Alyssa solve the classic chicken and egg problem for marketplaces in the early days with Hipcamp? How important does Alyssa believe it is for marketplaces to have truly differentiated supply? How does Alyssa think about what it takes to prevent leakage in marketplaces today? How can marketplace founders be strategic in building moats around their business? What works? What does not work when building marketplace defensibility?

3.) How does Alyssa manage the psychology of being CEO? What does Alyssa find to be the most challenging element of the role? What have been Alyssa’s biggest lessons from her last 12 months in the role? How has she seen her style of leadership change and develop over time? How does Alyssa deal with the shit hit the fan moments?

4.) How did Alyssa find the fundraising process for Hipcamp? Why did Alyssa wait 5 years before raising the Series A? What changed in the business that made Alyssa realise then was the right time to raise big? How did the Series B with a16z and Andrew Chen catalyse so fast? Why did Alyssa select the investors she did? What investors did Alyssa not select or not select her that she would also loved to have worked with?

Items Mentioned In Today’s Show:

Alyssa’s Fave Book: The Overstory: Shortlisted for the Man Booker Prize 2018, Uncanny Valley: A Memoir

As always you can follow HarryThe Twenty Minute VC and Alyssa 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: How To Assess Risk and Value Creation, Why It Would Be Better If VCs Had Smaller Portfolios & How To Optimise Internal Decision-Making with Misha Esipov, Founder & CEO @ Nova Credit

Misha Esipov is the Founder & CEO @ Nova Credit, the startup that allows you to use your international credit history to apply for credit cards, apartment rentals, loans and more. To date, Misha has raised over $70M with Nova from some of the best in the business Kleiner Perkins, Index, First Round and General Catalyst to name a few. As for Misha, prior to changing the world of credit history, he spent over 5 years in the more traditional world of finance including time at Apollo in the world of private equity and then also Goldman Sachs in the world of investment banking. If that was not enough, due to the incredible impact Nova Credit is having, Misha also sits on the board of World Education Services.

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In Today’s Episode You Will Learn:

1.) How Misha made his way from the world of investment banking and private equity with Goldman and Apollo to changing the way we think about international credit with the founding of Nova?

2.) How does Misah think about and asses both risk and value creation? How did Misha’s time at Goldman Sachs influence his operating mentality and how he thinks about the value of data today? Why does Misha find the growth at all costs and revenue later mindset challenging? What core fundamentals around unit economics did Misha establish early with Nova? How does Misha advise founders when it comes to unit economics?

3.) Misha has raised over $69M from some of the best, how did Misha find the process of fundraising? Where specifically does Misha believe his investors provide outside value? What is the optimal way to use an investor in the recruitment process? Where does Misha believe investors could do better and improve? How does Misha advise founders when it comes to manager selection?

4.) How does Misha manage the psychology of being CEO? How does he deal with the shit hit the fan moments? How has his role changed over the last 3 years? What elements have been the most challenging to learn and scale?

5.) How does Misha advise founders on building a diverse pipeline of recruitment candidates from day 1? Why does Misha believe that no recruitment firm can solve for diversity? What is his process as a result for ensuring a truly diverse team? What works? What does not? How does Misha building a culture of accountability? How does Misha think about optimising internal decision-making?

Items Mentioned In Today’s Show:

Misha’s Fave Book: Mastery (The Robert Greene Collection)

As always you can follow HarryThe Twenty Minute VC and Misha 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: 3 Addictions of Early-Stage Startup Founders, How Founders Should Strategically Think Through Unit Economics From Day 1 & Why Micromanagement Can Be Beneficial In The Early Days with Adena Hefets, Co-Founder @ Divvy Homes

Adena Hefets is Co-Founder @ Divvy Homes, the startup that turns your monthly rent into a down payment allowing you to get on the property ladder, sooner. To date, Adena has raised over $189M with Divvy from some of the best in the business including a16z, Ray Tonsing @ Caffeinated, Max Levchin, DFJ and Threshold Ventures to name a few. Prior to founding Divvy, Adena was an early-stage fintech investor at DF. Before the world of venture, Adena was part of the original team that started Square Capital and grew the product to over 10,000 advances ($50M) within 1 year. Prior to that, Adena started her career in the world of private equity with TPG.

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In Today’s Episode You Will Learn:

1.) How Adena made her way from the world of venture with DFJ to changing the way we think about homeownership with Divvy?

2.) What does Adena believe are the 3 addictions of many early-stage startup founders? How does Adena advise founders on the right way to think about paid marketing? What have been some surprising lessons from seeing Divvy’s CAC change over time? How does Adena advise founders to construct a playbook and cadence for hiring?

3.) How does Adena think differently about unit economics today? Is it fundamental to have this mindset from Day 1? Where does Adena believe many founders go wrong when it comes to unit economics? Who is to blame for this desire for synthetic growth? The founders? The VCs?

4.) Considering female founders get a tiny portion of VC funds raised, how was the fundraise for Adena with Divvy? How does Adena advise other female founders and minorities on fundraising successfully? Does Adena believe that founders should always be raising? How does raising debt differ to raising equity? Why is it so much more challenging?

5.) Why does Adena believe that micromanagement can be beneficial in the early days? How does Adena ensure that it does not lead to dependencies and dejected team members? What does Adena to do push people to really get the most out of them? What works? What does not?

Items Mentioned In Today’s Show:

Adena’s Fave Book: Evicted: Poverty and Profit in the American City

As always you can follow HarryThe Twenty Minute VC and Adena 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: Matt Mochary, Coach To Silicon Valley’s Leading VCs & Founders on How To Deal with Imposter Syndrome and Self-Doubt, How To Manage Fear and Anger & Why Board Seats Are The Death of Investors

Matt Mochary coaches some of the world’s leading venture capitalists and founders helping them to build the best organizations possible. On the VC side, Matt has worked with Peter Fenton @ Benchmark, several Sequoia Partners, Hemant @ GC and Mamoon @ Kleiner to name a few. As for founders, Matt has worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport and more. Prior to coaching, Matt began his business career as an investor with Spectrum Equity Investors.  He then co-founded Totality, eventually sold to MCI/Verizon.  In his own words, Matt went on to have fun (making the Academy Award short-listed documentary Favela Rising) and do good (starting the Mochary Foundation).

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In Today’s Episode You Will Learn:

1.) How Matt made his way from growth investor to immensely successful founder to now coaching the world’s leading investors and founders?

2.) How does Matt advise founders to think about their relationship towards fear and anger? Why doe they generate bad quality of decision-making? What should be done when one recognises they are fearful or angry? Where do many founders and investors go wrong here?

3.) How does Matt advise founders who struggle with issues of self-doubt and imposter syndrome? What process should they go through to gain their confidence? What should they not do? How should they communicate their self-doubt to their team and the world?

4.) How does Matt advise founders in terms of the optimal communication strategy both with their team and their co-founders? Does radical transparency need to be instant or should it be timed correctly? What are the best conflict resolution strategies between founding teams?

5.) Why does Matt believe boards are the death of investors? Why are board members not optimally placed to advise their founders? What does Matt believe makes the best board members having worked with the likes of Peter Fenton? What does Matt advise new board members to be the best board member they can be?

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

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

I doubt you started a business to track financial statements or make cash flow spreadsheets. Now we have Pilot and Pilot for bookkeeping gives you back the freedom to focus on your business. Every month your dedicated account manager will send you an accurate, detailed financial report. Pilot does accrual basis bookkeeping in QuickBooks Online, so you’re never locked into a proprietary platform. Plus, you’ll work with the same person each month, so you can rely on them to become an expert in your business. Check them out today at pilot.com/20vc.


20VC: Why Most Founders Do Not Structure Their Fundraise Correctly, The Pros Of Having An MBA As A Startup Founder & How To Manage The Psychology Of Being CEO and Overcome Self Doubt with Iman Abuzeid, Founder & CEO @ Incredible Health

Iman @ Incredible Health

Iman Abuzeid is the Founder & CEO @ Incredible Health, the startup that connects hospitals with nurses and other high shortage healthcare professionals to dramatically speed up the hiring process. To date, Iman has raised over $17M with Incredible Health from some dear friends of the show including NFX, a16z, Charles Hudson @ Precursor and Obvious Ventures to name a few. As for Iman, prior to Incredible, she was a medical doctor, a McKinsey alumnus and led product management at AliveCor, a Khosla-backed health tech startup.

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In Today’s Episode You Will Learn:

1.) How Iman made her way into the world of startups from a family of surgeons and then through being a medical doctor herself?

2.) How was the fundraising process for Iman as a female minority founder? What advice would Iman give to other women and/ or minority when it comes to getting the very best investors? Where does Iman see so many founders make mistakes raising? How should founders structure their meetings with VCs?

3.) Where does Iman believe VCs can be most helpful? Where do many think VCs are helpful but they are actually not? What does Iman think of the “VC Twitter” ecosystem at play today? What investors said no along the way but Iman really liked? Why? Why does Iman believe MBA’s provide such an advantage to startup founders today?

4.) How does Iman manage the psychology of being a CEO? How does Iman deal with moments of self-doubt and imposter syndrome? How has Iman seen herself evolve and change as a leader over the last 3 years? What elements have been the most challenging to come to grips with?

5.) Why does Iman still believe if you are not building your startup in the bay, you are missing out? What is so special about Silicon Valley? What advice does Iman give to founders looking to build a diverse team from day 1? How does Iman think about inevitable hiring mistakes? When is the right time to pull the plug?

Items Mentioned In Today’s Show:

Iman’s Fave Book: The Hard Thing About Hard Things

As always you can follow HarryThe Twenty Minute VC and Iman 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: Index Ventures Partner, Mark Goldberg on The Questions Founders Must Ask A Multi-Stage Fund Before Taking Their Money At Seed, Why Most Angels Will Lose Their Money & Why We Will See Our First $100Bn Neo-Bank Shortly

Mark Goldberg @ Index Ventures

Mark Goldberg is a Partner @ Index Ventures, one of the leading venture firms of the last decade with a portfolio including the likes of Dropbox, Revolut, Supercell, Plaid and Transferwise to name a few. As for Mark, since joining Index he has largely specialised on all things financial services and sits on the board of Plaid, Nova Credit, Intercom, Pilot and more incredible companies. Prior to Index, Mark spent 3 years in BizOps at Dropbox where the company increased tenfold during his time there.

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In Today’s Episode You Will Learn:

1.) How Mark made his way into the world of venture with Index having spent 3 years at Dropbox during a transformational time for the company? What were Mark’s biggest takeaways from seeing the growth cycle at Dropbox? How did that impact his investing mindset with Index?

2.) Why does Mark believe that venture as an asset class is commoditising? What does Mark believe the best funds will have to do to stay ahead? How does Mark build relationships of trust and authenticity so early with founders? What works? What does not? What is the right way to deliver direct and tough feedback to founders?

3.) How does Mark feel about multi-stage funds re-entering seed investing again? What are the right questions seed founders should ask multi-stage funds when determining whether to take their money? What does Mark believe it takes to be competitive and win the very best of deals? How is the Founder <> VC dynamic changing with capital supply?

4.) Why does Mark believe that most angels are going to lose their money? What does Mark wish all angels knew when they started? How does Mark feel about the rise of founders investing alongside operating? What are the pros? What are the cons? How does Mark feel about the rise of scout funds? Where is there place in the ecosystem?

5.) We are seeing unparalleled levels of activity in fintech, is this a boom or are we at the start of a fundamental shift in the landscape? Why does Mark believe we will soon see our first $100Bn neo-bank? Why does Mark believe we will see a strong rise in the consolidatory environment for fintech moving forward?

Items Mentioned In Today’s Show:

Mark’s Fave Book: Barbarian Days: A Surfing Life

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

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

I doubt you started a business to track financial statements or make cash flow spreadsheets. Now we have Pilot and Pilot for bookkeeping gives you back the freedom to focus on your business. Every month your dedicated account manager will send you an accurate, detailed financial report. Pilot does accrual basis bookkeeping in QuickBooks Online, so you’re never locked into a proprietary platform. Plus, you’ll work with the same person each month, so you can rely on them to become an expert in your business. Check them out today at pilot.com/20vc.

20VC: Gusto Co-Founder, Tomer London on Why Most Founders Approach Fundraising With The Wrong Mindset Today, How To Construct A Values/Motivation Alignment Test To Determine The Right Investors For You & Why Delight Is So Crucial To The Success of Any Consumer Facing Product

Tomer @ Gusto

Tomer London is the Co-Founder @ Gusto, the people platform for small businesses providing one place to run payroll, manage benefits, and support your team. To date, Tomer and the team have raised over $520M with Gusto from some of the industry’s leading investors including General Catalyst, CapitalG, Kleiner Perkins, T Rowe, Fidelity and more and then individuals including Shopify Founder Tobias Luttke, Sam Altman, Max Levchin, Matt Mullenweg, Kevin Hartz and Elad Gil to name a few. Prior to Gusto, Tomer did a PHD in Electrical Engineering at Stanford and before that was Founder and CEO @ Vizmo, mobile self-service technologies for enterprise to try to fix customer care.

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In Today’s Episode You Will Learn:

1.) How Tomer made his way from creating inventory management software for his Father’s small business in Israel to Stanford and founding the unicorn that is Gusto?

2.) Why does Tomer believe that most founders approach fundraising with the wrong mindset today? What does he mean when he says, “fundraising = creating change”? What is the “values motivation alignment”? How can founders use it to help them select the right investor for them? Why should you add investors just as you would new team members?

3.) Having raised over $200M in the latest financing, how does Tomer think about when is the right time to pour fuel on the fire and go big? Is it a fundamentally different mindset when you have so much cash thrown on you? What would Tomer advise founders with suddenly expanded budgets? With 111 investors on the Gusto cap table, what would Tomer advise founders when it comes to cap table management?

4.) What have been Tomer’s biggest learnings when it comes to building a delightful product at scale across different segments? How important does Tomer feel time to delight from the UX perspective is? How does Tomer think about testing levels of user delight? NPS? Product analytics? How does Tomer think about the balance between product development and going all out for scaling?

5.) How has Tomer seen himself change and evolve as a leader of the last 5 years? What elements has he found super challenging to come to grips with? Where does Tomer believe he has a superpower on the flip side? Question from Laela @ CapitalG, what specifically did you do to create the culture that you did in the early days?

Items Mentioned In Today’s Show:

Tomer’s Fave Book: No Room for Small Dreams: Courage, Imagination and the Making of Modern Israel

As always you can follow HarryThe Twenty Minute VC and Tomer 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.

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