The Full Ratchet (TFR): Venture Capital and Startup Investing Demystified

On this special segment of The Full Ratchet, the following individuals are featured: Nick Moran Kwame Boler This will be a unique segment where, Founder of Neu, Kwame Boler, will discuss his startup story and how he chose New Stack to participate in the funding round. To listen more, please visit http://fullratchet.net/podcast-episodes/ for all of our other episodes. Also, follow us on twitter @TheFullRatchet for updates and more information.

On this special segment of The Full Ratchet, the following Investors are featured: Minnie Ingersoll Oren Klaff Jason Whitney Nikhil Basu Trivedi Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach.

Niko Bonatsos of General Catalyst joins Nick to discuss Investing in First-time Founders, the Evolution of Social, the Future of Big Tech, and the Freedom of Remote Work. In this episode, we cover: Walk us through your background and path to VC What's the thesis at General Catalyst? Livongo... up nearly 300% since public debut last year — I hear you were in the room during the early formation stages. You have been at GC for almost 10 years — what has been the most significant change in VC, aside from the pandemic, since you began your career? What are your thoughts on the explosion of seed funds and now many angel funds as well? Since the pandemic broke, what's been the most significant adjustment at GC, and/or how do you see the approach to investing changing going forward? What surging trends during the pandemic will continue to grow faster, and which will revert once the pandemic is over? Do you think this fundamentally changes benefits that are offered to employees? I'm not sure if you caught the recent documentary on Netflix — social dilemma explaining social media issues. Many experts argued that we are not evolved to handle all of these inputs and that big tech has and will continue to manipulate our beliefs and actions. What's your take? Tweet: "Are you building a consumer product that is perceived as annoying, controversial, or stupid by most people? If yes, I'd love to hear from you!" What are some examples of consumer successes that started this way? What qualities does a founder need to have for you to be interested in? Break up big tech? The three data points

On this special segment of The Full Ratchet, the following Investors are featured: Alex Osterwalder Mark Suster Melody Koh Farooq Abbasi Each investor discusses sectors, drivers, and/or trends that may have a significant impact in the future and are potentially positioned for outsized-returns.

Villi Iltchev of Two Sigma Ventures joins Nick to discuss Using "George" a Proprietary Tool to Source Startups, The Commoditization of Capital, and the New Exit Environment. In this episode, we cover: Walk us through your background and path to VC What's the thesis at Two Sigma? Tell us about George. What's George's biggest blind spot? What is your decision framework on investments? What characteristics do you look for in markets when identifying new sectors/spaces of interest? How long after investing in/working with a company do you tend to know whether it's going to work or not? Do you attempt to handicap execution risk vs. technical risk vs. commercial risk? Capital is a commodity and, largely speaking, there doesn't appear to be a lot of differentiation in venture. How do you combat the commoditization of venture? Aside from bankers... who do you think stands to lose the most from the increase in SPACs and direct listings? Any other downsides, unintended consequences, or problematic issues that could arise from the increase in SPACs? A decade from now, will the U.S. be the best country to start a tech company? If it shifts, what are the prime candidate countries to replace the U.S.? International investment strategy for Two Sigma? Three data points... hypothetical investment scenario Let's say you're approached to invest in an enterprise SaaS startup. Founder has a great background. MRR is $200k, growing 20% MoM. LTV:CAC is 5:1. Quick Ratio greater than 4. Catch is, you can only ask 3 questions for 3 specific data points, in order to make your decision. What three questions do you ask?

On this special segment of The Full Ratchet, the following Investors are featured: Ty Findley Stephen McIntyre Beezer Clarkson Sarah Tavel Each investor highlights a situation where they decided not to invest, why they passed, and how it played out.

Janet Bannister of Real Ventures joins Nick to discuss Launching Canada's #1 Local Classifieds Site, Kijiji, The Flourishing Canadian Tech Ecosystem, and What to Look for in Early-stage Marketplace Startups. In this episode, we cover: Walk us through your background and path to VC What's the thesis at Real Ventures? Tell us about your time at Kijiji You became the Managing Partner at Real Ventures a few months before the pandemic. What timing to take on the MP role! You've talked about how it's just as important to focus on founder development as it is to focus on business strategy and growth... in what areas do you find that founders need the most development help? Largely speaking, what stats or trends across Canada lead you to believe that it will have a booming tech economy over the next decade? What city gets most of your attention and what city/region is under-the-radar but shouldn't be? What are the top 3 things you're looking for in a marketplace startup? come for tool stay for marketplace... vice-versa? Balanced scorecard Let's say you are approached to invest in a Consumer Marketplace company with $5M in GMV, a 30% take rate, and 20% MoM growth for the last 6 months. Catch is you can only ask for 3 data points to make your decision. What 3 questions do you ask for?

On this special segment of The Full Ratchet, the following Investors are featured: Tom Tunguz Grace Isford Ben Casnocha Courtney Reum Each investor discusses a portfolio company that did not survive and why it was that they failed.

George Arison of Shift joins Nick to discuss Going Public via SPACs and PIPEs, The First Mover in Ridesharing That Lost to Uber, and Building the Online Marketplace for Used Cars, Shift. In this episode, we cover: Walk us through your background and path to tech. What was the outcome of taxi magic? Shut down? When you spoke with Bill Gurley - rumor has it he pushed back on the model. Did you consider switching? What is Shift? How are you different than Carvana? How accurately can you price a car sight unseen? It feels like you are effectively CarMax online... If CarMax is such a good value prop for seekers and buyers, why do you think they only have a 1% market share? There were lots of ways you could have expanded early on... your offerings... geography... and even product/business lines (like financing)... talk us through the early decisions that were made and how they were made The name is great but does Gen Z get it? No one shifts anymore Online marketplace solving an extremely frustrating and time-consuming consumer life event but it's a very Infrequent transaction so you need to be top of mind when someone is buying a new car or ready to make a transaction... How are you thinking about that? Talk about your decision to go with a SPAC to go public. The decision to go direct-listing would be in cases where the company is more of a household name? SPACs were a four-letter word in the '90s... apparently, there were some bad situations... what is the risk here, and how has that been addressed by the modern SPAC structure? Do sponsors get 2% or 20% off the top? What was the value of the SPAC vs. the valuation of your company... were you (and other shareholders) diluted by the SPAC investment amount And the rest/the balance of capital comes from a PIPE, correct? As an investor, wouldn't the preference be to invest in the SPAC vs. the PIPE? Building a company in SV or not, and where that is headed? What advice would you have for founders before selecting VC partners? What was the experience as an openly gay man building a tech company -- do you think that presented a more difficult path to success?

On this special segment of The Full Ratchet, the following Investors are featured: Check Warner Ramy Adeeb Patrick Gallagher Shawn Carolan Each investor describes the most unusual situation or pitch that they've encountered as an investor.