20VC: Reddit’s Alexis Ohanian on How It All Started With Paul Graham @ YC, The Biggest Surprises About Making The Move Into VC & Why Alexis Believes All The Best Investors Have Operating Experience

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Alexis Ohanian is co-founder of Reddit & Initialized Capital. After graduating from UVA in 2005, Alexis and his co-founder Steve Huffman started Reddit, which they sold in 2006 to Conde Nast. In 2015, he returned to a full-time capacity with Steve Huffman as the two returned to the helm of a fully independent Reddit, which is now the 8th largest US website. In 2016, he joined Garry Tan in kicking off the third fund for Initialized Capital, an early stage venture capital firm. He’s invested in and advised over two hundred tech startups and was a partner at Y Combinator; Alexis has also written a national best-selling book, Without Their Permission and was named on Forbes 30 Under 30 list two years in a row.

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In Today’s Episode You Will Learn:

1.) How Alexis made his way into the world of VC from founding Reddit?

2.) What were the biggest surprises for Alexis about making the move into venture full time? What have been the biggest challenges?

3.) How do Alexis and Garry (Alexis’ partner) look to integrate process into their investing with Initialized? What is core to the success of this process? Why should more VCs be doing so?

4.) What does Alexis believe makes the best seed investors? What are the benefits of investors that have been in the trenches? How can they add to their companies in a way those without operating experience cannot?

5.) How does kindness integate into Alexis’ role as an investor? Can one win in investing while being kind? How does Alexis look to show his kindness to founders and investors?

Items Mentioned In Today’s Show:

Alexis’ Fave Blog: Reddit

Alexis’ Fave Book: Slaughterhouse 5 

Alexis’ Most Recent Investment: Workramp

As always you can follow Harry, The Twenty Minute VC and Alexis on Twitter here!

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

Pearl believes the latest automotive technology should be available to every driver – whether it’s time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it’s solar powered. Since RearVision is software based, we’re able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It’s also available on Amazon and through Crutchfield.

Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

20VC: Peter Weijmarshausen

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Peter Weijmarshausen is the CEO and Co-Founder of Shapeways, the world’s leading 3D printing marketplace and community. Shapeways have raised funds from some of the world’s leading investors including the likes of USV, Andreesen Horowitz and Index Ventures just to name a few. Prior to Shapeways, Peter was the CTO of Sangine, where he and his team designed and developed satellite broadband modems. Peter was also Director of Engineering at Aramiska, where he was responsible for delivering a business broadband service via satellite.

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In Today’s Episode You Will Learn:

1.) How Peter made his way into startups and came to found Shapeways?

2.) Where are we in the 3D printing cycle today? Has it developed slower or quicker than Peter expected? How was it for Peter inhabiting a space with so much hype?

3.) When does 3D printing make the transition from early adopter market to mass market? What are the determinants that will allow for this to happen?

4.) Having started life in an incubator, why did Peter decide that for the origin of Shapeways? What are the benefits? What type of founder is this model right for?

5.) Shapeways have raised from Index, USV and a16z, so how was the fundraising journey for Peter? What would he like to improve upon for next time? What did he do well?

Items Mentioned In Today’s Show:

Peter’s Fave Blog: New York Times

Peter’s Fave Book: Leadership and Self-Deception

As always you can follow Harry, The Twenty Minute VC and Peter on Twitter here!

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

Pearl believes the latest automotive technology should be available to every driver – whether it’s time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it’s solar powered. Since RearVision is software based, we’re able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It’s also available on Amazon and through Crutchfield.

Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

20VC: Kara Nortman

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Kara Nortman is a Partner @ Upfront Ventures, one of LA’s leading venture funds. Kara is also co-founder of Seedling where she currently serves as Chairman. Prior to starting Seedling, Kara spent close to seven years at IAC where she acted as the Senior Vice President and General Manager of Urbanspoon and Citysearch. Prior to Urbanspoon/Citysearch, Kara co-headed the M&A group at IAC where she lead some of their most successful acquisitions, notably Urbanspoon, Dictionary.com and Aston Hotels. While at IAC, Kara also served as a board member to Hatch Labs, IAC’s mobile technology incubator, where she recruited and advised Tinder. Kara also spent time at Morgan Stanley, Microsoft, and Battery Ventures.

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In Today’s Episode You Will Learn:

1.) How Kara made her way into the wonderful world of VC?

2.) Question from Greg Betinelli and Jenny Lefcourt: What is the most surprising thing about moving from an operator to a VC? What does Kara prefer more about being a VC?

3.) Having been an entrepreneur with a board, what does a good board member look like to Kara? How does Kara allocate her time amongst her portfolio?

4.) How does Kara assess founder psychology? How does Kara look to get to know the founder both post and pre-investment? What are some signs and tells for Kara of the truly successful operators?

5.) How does Kara view diversity in the VC landscape? What are prime examples of where it is going wrong? What can be done to change this? What are Kara’s hopes and concerns for the future?

Items Mentioned In Today’s Show:

Kara’s Fave Blog: Both Sides of The Table

Kara’s Fave Book: Grit by Angela Duckworth

Kara’s Most Recent Investment: Stem

As always you can follow Harry, The Twenty Minute VC and Kara on Twitter here!

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

Pearl believes the latest automotive technology should be available to every driver – whether it’s time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it’s solar powered. Since RearVision is software based, we’re able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It’s also available on Amazon and through Crutchfield.

Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

20VC: Lessons Learnt From Marc Benioff & Selling To Salesforce For $2.7bn, What Product Market Fit Really Looks Like & Why Pricing Is Startup’s Biggest Problem with Scott Dorsey, Managing Partner @ HighAlpha

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Scott Dorsey is the Managing Partner @ High Alpa, the startup studio that both builds and invests in some of the most exciting SaaS companies today. Prior to HighAlpha, Scott was a successful entrepreneur who co-founded ExactTarget and led the company from start-up to global marketing software leader. ExactTarget went public on the New York Stock Exchange in March 2012 and sold to Salesforce.com in July 2013 for $2.7 billion. At Salesforce, Scott worked directly with Marc Benioff to execute the ExactTarget vision within Salesforce.

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In Today’s Episode You Will Learn:

1.) How Scott made his way into the world of venture from founding ExactTarget?

2.) What was it like to work directly for Marc Benioff? What were the biggest learnings and takeaways? What were the biggest challenges?

3.) With a startup studio producing companies and a fund investing in them, how does Scott avoid the negative signalling that is inherent within these 2 structures?

4.) Having seen so many successful SaaS startups, what does product market fit look like to Scott? From the studio, what are the biggest challenges his startups face in hitting product market fit?

5.) What are the fundamentals that all startups should focus on in the quest for product market fit? What are the challenges? How should this be measured?

Items Mentioned In Today’s Show:

Scott’s Fave Blog: SaaStr

Scott’s Fave Book: Good To Great by Jim Collins

As always you can follow Harry, The Twenty Minute VC and Scott on Twitter here!

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

Pearl believes the latest automotive technology should be available to every driver – whether it’s time for you to buy a new car or not. RearVision is our first step in driving this commitment forward. Pearl RearVision is the only wireless backup camera and alert system that installs in minutes and updates throughout its lifetime. Pearl literally takes less than 10minutes to install and is completely wireless because it’s solar powered. Since RearVision is software based, we’re able to push updates and new features over the Pearl App in the exact same way you receive updates for other apps on your phone. Pearl RearVision is perfect for anyone who wants to upgrade their car in minutes. Pearl RearVision is $499.99 and available at PearlAuto.com. It’s also available on Amazon and through Crutchfield.

Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at xero.com/20vc

20VC: Flexport’s Ryan Petersen on Why Investor Relations Are Overrated, Why Boards Have To Be Rethought & Why MBAs Do Not Make Bad Entrepreneurs

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Ryan Petersen is the Founder and CEO of Flexport, the freight forwarder for the internet age. Flexport recently raised a phenomenal $65m Series B from the likes of Founders Fund, First Round, Felicis, Bloomberg Beta, Yuri Milner, Susa Ventures and more incredible investors. With none other than YC founder Paul Graham stating ‘Ryan has the rare ability to not just satisfy the market but grow it’. Prior to Flexport, Ryan was Founder and CEO of ImportGenius.com, the largest provider of business intelligence to the import-export industry.

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In Today’s Episode You Will Learn:

1.) How Ryan came to found Flexport? What was the a-ha moment for him?

2.) Why does Ryan believe it is crap that MBA’s do not make good entrepreneurs? How did Ryan design his life to be an entrepreneur without the opportunity to work for someone else?

3.) How has Ryan found the experience of being a single founder? What are the pros and cons? What was the investor reaction? What does Ryan advise other single founders?

4.) How did Ryan find the fundraising for the latest $65m raise? What did he do well? What would he like to improve upon for later rounds? How did he educate investors without being patronising?

5.) Why does Ryan want to see boards be rethought? What is so inefficient about boards? When did Ryan gain his board? What would Ryan advise fellow founders on building a board?

Items Mentioned In Today’s Show:

Ryan’s Fave Blog: SaaStr

As always you can follow Harry, The Twenty Minute VC and Ryan on Twitter here!

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

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Xero is beautiful, easy-to- use online accounting software for small businesses. With Xero, you can easily manage your accounting anytime, anywhere from your computer or mobile device.When you add Xero to your small business you are able to: Send online invoices and get paid faster. Get an instant view of your cash flow. Track your payroll and keep tabs on your inventory. Partner with your accountant and bookkeeper in real time whenever you like. You can also customize your Xero experience with over five hundred business apps, including advanced solutions for point-of- sale, time tracking, ecommerce and more. Sign up for a free thirty-day trial at Xero.com/twentyVC

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