SoftTech VC’s Andy McLoughlin on The Series A Crunch, Maximising Runway and Minimising Burn and For Startups

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Andy McLoughlin is a Partner with SoftTech VC, where he primarily invests in B2B, SaaS, developer tools and mobile applications. Prior to joining SoftTech, Andy was co-founder of London-based Huddle, under Andy’s leadership, Huddle became one of Europe’s most awarded and well-known technology startups, raising over $80M of venture funding to date. Since 2010 Andy has been a prolific angel investor building a portfolio covering 35 startups, mostly in the SaaS / B2B space. Just to name a few of the investments from his incredible portfolio Andy was an angel in the likes of Buffer, Intercom, Pipedrive, Postmates, Secret Escapes, just to name a few.

In Today’s Episode You Will Learn:

1.) How Andy made his startup as an entrepreneur and then VC?

2.) What was it that made Andy make the move from the world of entrepreneurship to VC?

3.) As a seed stage investor, what does Andy make of the Series A crunch? How prevalent has it been for him as an investor? What is the optimal amount of runway founders should raise for?

4.) What does Andy think of the size and cadence of the first funding rounds that we are seeing now? What does he make of the rise of the second seed or the bridge round? Is it an indication of trouble?

5.) SoftTech are near the closing of Fund V, so what is the thesis and the mission going forward? What themes and spaces is Andy most excited by and why?

Items Mentioned In Today’s Episode:

Andy’s Fave Book:

Andy’s Fave Blog or Newsletter:

Andy’s Most Recent Investment:

As always you can follow The Twenty Minute VCHarry and Andy on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

This episode was supported by Wunder Capital, the leading online investment platform that allows individuals to invest in large scale solar projects across the U.S. Wunder’s solar investment funds allow you to earn up to 11% annually, while diversifying your portfolio, curbing pollution and combating global climate change. Do well by doing good and sign up for a free account here and join the thousands of people that are already achieving their investment targets.

 

20VC: Gary Liu @ Digg on The Rebirth of Digg & The Evolution Of Content

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Gary Liu is the CEO @ Digg, the incredibly famous platform that allows users to find, read and share the most talked about stories on the internet. Prior to joining Digg, Gary was an early employee at Spotify holding numerous positions including, Head of Spotify Labs and Global Director of Ad Product Strategy. Gary joined Spotify from AOL, where he was the Director of Sales Strategy and Operations at Patch. Before joining AOL, Gary was a business and sales operations leader at Google and Clickable.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

In Today’s Episode You Will Learn:

1.) How Gary made his entry into the world of tech and later became CEO at Digg?

2.) What were Gary’s biggest takeaways from his time at Google and being an early employee at Spotfiy? How has he adapted those learnings to his role now at Digg?

3.) What really happened at Digg? What went wrong? Why did Digg not live up to the early hype of being the darling of the internet age? How are Digg evolving to change this?

4.) In the vastly competitive space of content creation and distribution, how do Digg stand out and differentiate themselves from the plethora of options available to consumers?

5.) How do Digg try to engage and unite the community through the commenting process without alienating people through the potential for malicious posts and trolling?

6.) How does a platform like Digg plan to monetize content with the ever disappearing ad dollar? Does it concern Gary or does he see potential in other avenues?

Items Mentioned In Today’s Episode:

As always you can follow The Twenty Minute VCHarry and Gary on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

20VC: Investing In The Next Frontiers Of Tech & Harry Potter with Adam Draper, Founder & CEO @ Boost VC

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Adam Draper is a fourth generation venture capitalist and the Founder & CEO @ Boost VC, a specialised seed stage accelerator that invests in blockchain and virtual reality startups. Before starting Boost, Adam angel invested in 20 companies including Coinbase, Plangrid and Practice Fusion. During his angel investment period, Adam was also the Founder of Xpert Financial in his aim to revolutionise the financial markets for private companies.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

In Today’s Episode You Will Learn:

1.) How Adam made his way into startups and the investing industry?

2.) Why is Adam so bullish on the topics of bitcoin and virtual reality?

3.) What are the fundamental use cases for bitcoin and why have we not seen mass adoption on a global scale so far? What are the barriers to adoption?

4.) What is the investment attitude to the bitcoin and VR space? Does the volatility of the price in bitcoin affect the level of investment going into the sector?

5.) What would Adam like to see more of in the space? What is he most excited for and where does he see the most potential?

Items Mentioned In Today’s Episode:

Adam’s Fave Book: The Name Of The Wind

Adam’s Fave Blog: Mugglenet

Adam’s Most Recent Investment: Joystream

As always you can follow The Twenty Minute VCHarry and Adam on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

 

20VC: Tim Draper on Investing In Tesla, The Best Pitch He Has Ever Seen & The Evolution of Venture and Startups

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Tim Draper is the founding partner of leading venture capital firms Draper Associates and DFJ. Some of his Venture successes include Skype, Baidu, Tesla, Hotmail, Twitch.tv, and hundreds of others. Fun fact about Tim, it was his original suggestion to use viral marketing in web-based email to geometrically spread an Internet product to its market was instrumental to the successes of Hotmail, YahooMail, and Gmail and has been adopted as a standard marketing technique by thousands of businesses. His prominence is evident through his being named 100 most influential Harvard Alumni, and seven on the Forbes Midas List. He was named Always-On #1 top venture capital deal maker.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

In Today’s Episode You Will Learn:

1.) How Tim made his way into startups and the investing industry?

2.) Having founded Draper Associates in 1985, how has Tim seen the investing landscape develop over time?

3.) Draper obviously invests across a variety of stage, but what is Tim’s preferred stage? Where does he see the most opportunity for venture returns? Why?

4.) Of all the companies Tim has seen, which was the best pitch? Why? Which founder inspired Tim the most? Looking back, is there anything you would have done differently?

5.) What is DraperU? What are the plans for the future? What is the vision? Why did Tim choose to do a reality show in StartupU? Has it been a very different experience being the lead in a TV show compared to investing in startups?

6.)Why is behind Tim’s immense belief in Bitcoin. Why is this? When did Tim realize the potential? How long will adoption take?

Items Mentioned In Today’s Episode:

As always you can follow The Twenty Minute VCHarry and Tim on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

20 VC: Niccolo De Masi @ Glu Mobile on Private Market Valuations, Being A Public Market CEO & The Trends Of Mobile Gaming

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Niccolo De Masi is the CEO & Chairman @ Glu Mobile, one of the world’s hottest gaming companies with title including the current No 1 Game in the App Store with the Kendall and Kylie Game, Glu is also the maker of the Kim Kardashian game and the likes of Deer Hunter and many more. Prior to Glu, Niccolo was CEO at mobile entertainment company Hands On Mobile and before that Niccolo was the CEO at London listed mobile entertainment company, Monstermob Group Plc.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

In Today’s Episode You Will Learn:

1.) How Niccolo came to be CEO at one of the world’s hottest gaming companies, Glu Mobile?

2.) How did Niccolo make the transition from feature phone business to smartphone business with Glu so successfully? How did Glu’s public market status affect the transition?

3.) How important is transparency within organisations as a leader, whether it be Founder or CEO? What are the important elements to communicate with your team and your investors?

4.) Why are private market valuations so misaligned with the public market? What will happen to the plethora of newly made unicorns?

5.) How does Niccolo source potential acquisition targets, what does he look for in, so called ‘well valued assets’? What makes them well valued?

6.) What is Niccolo’s turnaround strategy for his acquisition targets? How can Glu’s platform elevate companies that are in distress?

Items Mentioned In Today’s Episode:

Niccolo’s Fave Book: The Rise and Fall Of The Great Powers 

As always you can follow The Twenty Minute VCHarry and Niccolo on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

20VC: Tyler Willis on How To Be Innovative With Customer Acquisition and The Future Of Innovation

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Tyler Willis is probably one of the best angel investors around and has invested in seed stage companies that have gone on to raise from the likes of Index Ventures, Founders Fund, Khosla Ventures and others. Some of these investments include the likes of wildly popular ride sharing app Lyft, the incredible Patreon (now delivering 2m a month to creators) and Change.org which now has over 80m users.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

In Today’s Episode You Will Learn:

1.) How Tyler made it into startups and the investing industry?

2.) Where does Tyler sit on investor specialisation? Is it best to have preferred sectors and round sizes?

3.) What elements are essential for Tyler pre investment and what can be tweaked later down the line?

4.) Question from Arielle Zuckerberg: How does Tyler evaluate customer acquisition so well? What is his approach to this with potential investments and portfolio companies?

5.) Why are people so negative on the future of innovation? Is Founders Fund’s ‘we expected flying cars and instead got 140 characters’ fair?

Items Mentioned In Today’s Episode:

Tyler’s Fave Book: Innovator’s Dilemma by Clayton Christensen

Tyler’s Fave Blog or Newsletter: Mattermark Daily

As always you can follow The Twenty Minute VCHarry and Tyler on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

20 VC: Arielle Zuckerberg, Partner at Kleiner Perkins Caufield & Byers

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Arielle Zuckerberg, Partner @ Kleiner Perkins Caufield and Byers. Arielle Zuckerberg joined KPCB in 2015 and focuses on early-stage investments in the firm’s digital practice as part of the venture team. Arielle joined Kleiner from Humin, where she led product for the company’s mobile apps. She started her career as a product manager by day and Hackathon host by night at Wildfire Interactive, Inc., which was acquired by Google in 2012. After the acquisition, Arielle worked as a product manager on social ads at Google. Outside of KPCB, Arielle has made several angel investments across the food tech and health sectors in the likes of Partender, Bitty Foods and The Ticket Fairy, just to name a few.

We would like to say a special thank you to Mattermark for providing all the data used in the show today and you can check out Mattermark Search here!

In Today’s Episode You Will Learn:

1.) How Arielle made it into startups and the investing industry?

2.) What has the move been like from angel to VC? What theories and investment theses are adjustable? How doe the fiduciary responsibility to your LP’s adjust your risk profile when investing?

3.) Questions from Tyler Willis: How does Arielle evaluate new products? How does Arielle learn and how does Ariele come down on the learning curve on new things so quickly (new investor to KPCB in ~2 years, for example).

4.) Arielle has now spent her first few months in venture, what have been the biggest surprises? Biggest challenges? What is Arielle’s fave part and what is her least fave part?

5.) How does Arielle see the AI space now? Where does she see room for innovation? Is there anything Arielle is concerned about?

6.) Now when doing research for this interview I came across Arielle’s New Years Resolution list from 2012! So what are your new years resolutions for 2016? What are the goals you are aiming for?

Items Mentioned In Today’s Episode:

Arielle’s Fave Book: The Symposium by Plato

As always you can follow The Twenty Minute VCHarry and Arielle on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

20VC FF 035: Why Crowdfunding Is Not Right For Tech Startups with Ryan Caldbeck @ CircleUp

Ryan Caldbeck is the Founder & CEO @ CircleUp, the online investing platform that allows you to invest in innovative consumer companies. They have raised funding from some of the best including USV, Maveron and Canaan Partners (all past guests). Before Ryan founded CircleUp, he worked in consumer product and retail-focused private equity at TSG Consumer Partners and Encore Consumer Capital, where he was exposed to hundreds of great consumer and retail businesses that were too small to obtain funding through the customary private equity channels and did not fit the risk profiles many VCs demanded. As a result, Ryan decided to build the solution, a private equity marketplace with the economics and scale to make funding available to these promising companies.

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In Today’s Episode You Will Learn:

1.) How did Ryan make the move from the world of VC to founding his own tech startup?

2.) Why is CircleUp marketplace investing, not crowdfunding? What does Ryan believe are the misnomers around the term crowdfunding?

3.) Where does this sector make sense and where is it  inefficient? Why is it wrong for tech companies?

4.) One major aspect in the UK that this segment has struggled with is it’s ability to attract institutional investors to the sector. So with CircleUp, how are institutional investors getting into this market and is there anything more Ryan would like to see with this regard?

5.) To what extent does Ryan think this is disrupting private capital formation? Should VCs be concerned? What sector of the funding environment is most vulnerable to being disrupted by the rise of marketplace investing?

6.) How was the funding process for Ryan? CircleUp raised over $50m over several rounds with investors from our friends at USV and Maveron, how that came about and what Ryan would advise founders entering the process?

Items Mentioned In Todays Show:

Ryan’s Fave Blog: AVC, Jeff Jordan, Bill Gurley

As always you can follow The Twenty Minute VC and Harry on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!
This episode was supported by Wunder Capital, the leading online investment platform that allows individuals to invest in large scale solar projects across the U.S. Wunder’s solar investment funds allow you to earn up to 11% annually, while diversifying your portfolio, curbing pollution and combating global climate change. Do well by doing good and sign up for a free account here and join the thousands of people that are already achieving their investment targets.

20VC: The First Online Venture Fund Built On AngelList with Dustin Dolginow @ Maiden Lane

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Dustin Dolginow is the General Partner @ Maiden Lane, the first online venture fund which uses AngelList as it’s operating system, serving as the institutional capital partner to the best angel investors in the world. Dustin has made investments in the likes of Getable, PipeDrive, Beepi and many more incredible companies. Dustin is also a venture partner with Accomplice where he serves some of the best entrepreneurs on the planet. Prior to investing, Dustin cut his teeth in the operations game with Social Swipe, which allowed merchants to gain more value from their transaction data.
In Today’s Episode You Will Learn:

1.) How Dustin made it into startups and the investing industry?

2.) What were Dustin’s major takeaways from his operational experience and how has he applied them to his role investing with Maiden Lane?

3.) Where does Ryan you democratisation of funding going in the next five years? What direction does Dustin believe we are moving in?

4.) Dustin has said that ‘capital is a crappy differentiator’ so what value add should founders look for in their VCs? How are we seeing the VC value add evolve over time?

4.) How does Dustin sell Maiden Lane in the sea of seed funds that have emerged over the last few years? How important does Dustin think it is for VCs and funds to have personal brands? What is bigger the brand of the VC or the fund?

5.) What is it Dustin looks for in products? Are there any must haves? Any design requirements?

Items Mentioned In Today’s Episode:

Dustin’s Fave Book:

Dustin’s Most Recent Investment:

As always you can follow The Twenty Minute VCHarry and Dustin on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

This episode was supported by Wunder Capital, the leading online investment platform that allows individuals to invest in large scale solar projects across the U.S. Wunder’s solar investment funds allow you to earn up to 11% annually, while diversifying your portfolio, curbing pollution and combating global climate change. Do well by doing good and sign up for a free account here and join the thousands of people that are already achieving their investment targets.

 

20VC: Gil Penchina @ Flight.vc

Gil Penchina is the Founder @ Flight.vc, a network of AngelList syndicates that covers a wide range of sectors from SaaS to security from Israel to England. Gil also has the title of the largest raise for an AngelList syndicate, essentially turning himself into a one man fund. Some of Gil’s investments include the likes of Paypal, Indiegogo, AngelList, Linkedin and many more. Prior to his investing career, Gil cut his teeth with operating roles at numerous companies including Ebay. We would also like to wish Gil the best of luck in his nomination for Angel Investor of The Year at tonight’s Crunchies by TechCrunch.
In Today’s Episode You Will Learn:

1.) How Gil made it into startups and the investing industry?

2.) Why did Gil choose numerous syndicate approach over one huge syndicate? What are the benefits of having numerous specialized syndicates?

3.) What is included in Gil’s sell of Flight as an investor? What is the driving force behind the success of Flight? What is the biggest challenge within this job as founder?

4.) How does Gil try and convince the startups that the syndicate method of investment is better for them? How does Gil portray his value add to startups?

5.) Does Gil insist on pro-rata rights? Should founders always grant them to early stage investors?Which VCs does Gil like to work with and what makes them a good VC?

6.) Where does Gil see the future of first AngelList? Will it replace the archaic system of VC? What are Gil’s plans for his syndicates? Is Gil looking to move into Series A and B rounds? How do you plan to become the Fidelity of this asset class?

Items Mentioned In Today’s Episode:

Gil’s Fave Book:

Gil’s Fave Blog or Newsletter:

Gil’s Most Recent Investment:

As always you can follow The Twenty Minute VCHarry and Gil on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

This episode was supported by Wunder Capital, the leading online investment platform that allows individuals to invest in large scale solar projects across the U.S. Wunder’s solar investment funds allow you to earn up to 11% annually, while diversifying your portfolio, curbing pollution and combating global climate change. Do well by doing good and sign up for a free account here and join the thousands of people that are already achieving their investment targets.

20 VC FF 034: What Fintech Can Learn From Uber and The Shift From Financial Organisation To Financial Efficiency with Kelly Peeler, Founder & CEO @ NextGenVest

Kelly Peeler is the Founder and CEO of NextGenVest, the College Money Mentor for every student, helping students navigate the financial aid and student loan application process. While at Harvard, Kelly started Business Across Borders, a non profit that helps Iraqi students rebuild their own economy by starting their own companies and the International Women in Business Summit, bringing together top female college leaders. She was selected as one of the eight Kauffman Foundation Global Scholars, named by Goldman Sachs as one of the 100 Most Intriguing Entrepreneurs, and named a White House #StartTheSpark Ambassador. Her TED Talk is called “How to Change the World as a Millennial – Don’t be Stupid with Money” and can be found here.
A special thank you to Mattermark for providing all the data displayed in today’s show and you can find out more about Mattermark here! 
In Today’s Episode You Will Learn:

1.) How Kelly made it into startups and what was the origin story for NextGenVest?

2.) How has the Fintech ecosystem evolved over the last 5 years compared to the mass of consumer facing fintect startups today? What does Kelly mean by Fintech 1.0 and the next phase of Fintech?

3.) How can emerging brands and in particular fintech brands build loyalty with the emerging millennial generation? What is the attention graph for millenials looking like?

4.) What does Kelly mean when she states a shift from financial organisation with Mint to financial efficiency today?

5.) What key determinants that have made Uber so successful can be used within Fintech startups to build the same trust and relationship?

6.) What is Kelly’s view of startups taking a platform dependent approach? What are the benefits and what are the concerns?

Items Mentioned In Today’s Episode:

As always you can follow The Twenty Minute VCHarry and Kelly on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

20VC: The Evolution Of Mobile & The Importance Of Follow On Funding with Hadley Harris @ Eniac Ventures

Hadley Harris is the Founding General Partner at Eniac Ventures, the first seed stage venture fund focussed exclusively on mobile. Eniac’s investments include the likes of Soundcloud, Airbnb, Elevate and many more incredible mobile first companies. Before Eniac, Hadley was a two-time entrepreneur in the mobile space, as an executive at Vlingo, acquired by Nuance Communications for $225m and after Vlingo he became CMO of Thumb, which was acquired by Ypulse. Hadley also worked at Charles River Ventures where he spent time helping with mobile investments while looking for a young startup to join. As if his portfolio does not prove enough of what a seed stage investing legend he is, he was also named by Business Insider as ‘New York’s Best Early Stage Investor’.
A special thank you to Mattermark for providing all the data displayed in today’s show and you can find out more about Mattermark here! 
In Today’s Episode You Will Learn:

1.) How Hadley made it into startups and the investing industry?

2.) What does an engineering degree provide when investing? Why did Eniac decide to focus solely on mobile?

2.) How has Hadley seen the NY venture and startup scene develop over the last years? Does an ecosystem need anchor companies to be great? Ex-Googlers, and ex-Facebook, ex-LinkedIn, ex-Sun, etc. are so important to the Bay Area ecosystem. What are New York’s anchor companies? How has that affected the ecosystem?

3.) What is it like helping companies like Soundcloud and Airbnb scale when in hyper growth mode? At the seed level, how important a role does valuation play when determining whether to invest or not?

5.) Why is raising a Series B so tough? Is it the embodiment of the funding barbell? Has NYC, like London, seen a rise in the second seed round?

6.) What are Hadley’s thoughts on VC founder alignment? What are the common characteristics of the best founders that Hadley has worked with and invested in?

Items Mentioned In Today’s Episode:

Hadley’s Fave Book:

Hadley’s Fave Blog or Newsletter:

Hadley’s Most Recent Investment:

As always you can follow The Twenty Minute VCHarry and Hadley on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!

Index’s Martin Mignot on Sourcing Rocketship Companies, Evaluating Founders and His Attitude Towards Risk At The Early Stage

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Martin Mignot is an early stage investor at Index Ventures where he specialises in SaaS, marketplaces and mobile. He is actively looking after Index’s investments in Algolia, Blablacar, Capitaine Train, Deliveroo, Drivy, Rad, Swiftkey and TheFamily. He worked on 50+ transactions to date, including Assistly, Auxmoney, BaseCRM, Cloud.com, Codecademy, DimDim, Factual, Farfetch, Flipboard, Funding Circle, Gluster, HouseTrip, Just-Eat, Lookout, Nastygal, Notonthehighstreet, Onefinestay, PeoplePerHour, TrustPilot, Soluto and SoundCloud.  Prior to joining Index, Martin was in the TMT team at UBS Investment Bank and co-founded the beauty subscription business Boudoir Prive (acquired by Joliebox/Birchbox) and a student web radio service (www.rsp.fm).
A special thank you to Mattermark for providing all the data displayed in today’s show and you can find out more about Mattermark here! 
In Today’s Episode You Will Learn:

1.) Where did it all start for Martin? What is the Martin Mignot story?

2.) How does Martin view venture as a career vs coming into it later on? Why does Martin think venture is now a viable career from the offset?

3.) Does Martin agree with Sheryl Sandberg’s statement, it doesn’t matter where you sit, as long as you have a seat on the rocketship? How important is valuation for Martin when making the decision?

4.) How Martin goes about sourcing the latest and greatest startups from the European ecosystem?

5.) How does Martin evaluate founders and consider their ability to execute on their plan, prior to making the investment?

6.) Talking of difficulty for startups attaining funding, what are your thoughts on VC founder alignment? You have said to focus before on the business and not the team, unless exceptional cases prevail, this is very strange for me to hear. Why is it you have adopted this stance and why do you feel it is best?

Items Mentioned In Today’s Episode:
Martin’s Fave Blog or Newsletter:
As always you can follow The Twenty Minute VCHarry and Martin on Twitter here!
If you would like to see a more colourful side to Harry with many a mojito session, you can follow him on Instagram here!