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

On this special segment of The Full Ratchet, the following Investors are featured: Grace Isford Erik Torenberg Eric Collins Villi Iltchev Each investor discusses sectors, drivers and/or trends that may have significant impact in the future and are potentially positioned for outsized-returns.

Vincent Diallo of Interlace Ventures joins Nick to discuss Retail Apocalypse or Renaissance, the Commerce Evolution, and Fundraising from Corporates. In this episode, we cover: Article Mentioned in Episode: http://bit.ly/TFR-Vincent Walk us through your background and path to VC What's the thesis at Interlace? COVID has affected commerce severely -- for better and for worse. Has this changed your investment approach? Many investors are avoiding all physical retail as COVID has created a "retail apocalypse", but you've stated that you see it more as a retail renaissance. Why? What are some trends from COVID that you think investors are overreacting to that you expect will return to pre-pandemic levels? What new consumer experiences or behaviors are emerging that you are excited about? You mentioned supply chain as another area of interest, where are the biggest opportunities in the supply chain? Biggest mistake fundraising? Biggest win fundraising? Oper8tor program? Is now a good time or a difficult time to be a diverse fund manager?

On this special segment of The Full Ratchet, the following Investors are featured: Tom Tunguz Patrick Gallagher Trae Vassallo Brian Hirsch Each investor highlights a situation where they decided not to invest, why they passed, and how it played out.

Sach Chitnis of Jump Capital joins Nick to discuss Discovering the Next Sectors of Opportunity, The Impact Platform, & The Exit Discussion. In this episode, we cover: Walk us through your background and path to VC What's the thesis at Jump Capital? Talk about developing a thesis on a specific market opportunity — can you give us the broad strokes on your process of how you dissect emerging markets and identify where existing offerings are lacking? How do you determine who will be the winner? Is it common that, of the existing set of players, none will emerge as the winner and you need to wait for a fresh approach? Having a portfolio support platform is unusual for your size — how are you able to make it work at your fund size and what all does it entail? In what areas do you find a Series A funded company needs the most help? How do you advise a founder that's in a hot space, doesn't need capital but has inbound interest and large investment offers, maybe at inflated valuations, from tier 1 coastal investors? Let's talk about exits a bit... you've been around for 8 years, I noticed the good news of both 4C and Personal Capital's recent large exit, where are you finding most of the exit discussions begin... do they start w/ the founder considering it, do you discuss it as an option, or do meetings/partnerships start coming from strategics that get the process rolling? How do you advise founders on negotiation and getting the right offer, not just any offer? What is "swing time" and how do you systematically build that into your schedule?

On this special segment of The Full Ratchet, the following Investors are featured: Niko Bonatsos Melody Koh Ramy Adeeb Mark Suster Each investor discusses a portfolio company that did not survive and why it was that they failed.

Maren Bannon of January Ventures joins Nick to discuss Breaking the Founder Stereotype, Mastering Conviction Over Zoom, & the Contrast between European and American Entrepreneurs. In this episode, we cover: Walk us through your background and path to VC What's the thesis at January Ventures? How are you and your team at January Ventures making tech more of an equal opportunity? What is your approach to portfolio construction in this fund and how will that evolve in the future? What's one thing you know now that you wish you knew prior to raising the fund? You take meetings with founders VERY early — no warm intro, no pitch deck, or no revenue required to pitch to January Ventures. How do you evaluate the potential this early? How do you filter all of the opportunities -- what is your pre-filter process? How have you changed your work/process at January post COVID? What is your experience like moving from SF to Europe and what is your view of the European tech ecosystem?

On this special segment of The Full Ratchet, the following Investors are featured: Henrique Dubugras Jim Douglass Beezer Clarkson Avichal Garg Each investor describes the most unusual situation or pitch that they've encountered as an investor.

Tim Guleri of Sierra Ventures joins Nick to discuss Advice from a Unicorn Founder Turned VC, the Future of the VC Landscape for Founders & VCs, and the Founder Love Metric. In this episode, we cover: Walk us through your background and path to VC What's the thesis at Sierra Ventures? What's been your biggest influence on the firm's ethos? You've had two incredible outcomes as a founder... first question is do you think the process of building a company today is materially different than it was when you did it... if so how? We've talked a lot on the show, over the past 8 months about the effects of COVID on venture... what have been you main observations on how VCs are adjusting to investing during COVID? What do you think the new normal for startups looks like post-covid? How do you advise a founder that's in a hot space, doesn't need capital, but has inbound interest and large investment offers, maybe at inflated valuations, from tier 1 coastal investors? How do you handle situations where the product is just not a great fit for the market and the momentum is not building the way it should? You've been through the exit process this yourself and, I'd imagine, even w/ great outcomes those are some of the hardest decision one faces as a CEO... Do you have a framework or an approach to assessing whether an exit offer is strong and should be taken or whether the founder should hold out for a bigger outcome. There are a lot of factors that play into having to wind down a company... are there any that standout that signal to you that it's no longer working and we need to face to reality? You mentioned something interesting recently pertaining to your relationship with founders and that's that you track a metric that you dub "Founder Love". Can you explain how you gauge and measure this? What do you think the venture industry looks like in 5-10 year

On this special segment of The Full Ratchet, the following Investors are featured: Check Warner Ty Findley Lo Toney Byron Deeter Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach.

Ed Sim of boldstart ventures joins Nick to discuss: Velocity as a Superpower, Why Contrarians Win, The Role of a Board Member, and Why Some Challenge When they Should Chill Walk us through your background and path to VC What's the thesis at boldstart ventures? What was it like starting Boldstart in NYC in 2010? Tell us a bit about the thesis at investment and how things evolved over the years until the ultimate exit? What's your preference... Niche and narrow problems or big and expansive opportunities? What is your mental model for investing in enterprise founders with ideas? category creation Why only technical founders? Will this enterprise bull market sustain? You've talked about being involved and sitting on boards from "whiteboard to scale" ?... how do you manage ever-increasing board responsibilities with other demands of the job? Where are VCs most lacking when it comes to the value that early-stage founders require? Do you think there's too much money in venture? How do you win in a seed with so many seed funds?

On this special segment of The Full Ratchet, the following Investors are featured: Steve Blank Niki Pezeshki Lolita Taub Jesse Middleton Each investor discusses sectors, drivers and/or trends that may have significant impact in the future and are potentially positioned for outsized-returns.

Brian Hirsch of Tribeca Venture Partners joins Nick to discuss Maintaining a Disciplined Fund Size and Strategy, The Rise of NYC Tech, and Changes in the Exit Environment. In this episode, we cover: Walk us through your background and path to VC What's the thesis at Tribeca Venture Partners (TVP)? We've seen notable firms in the valley launch platform and service offerings to founders... have you considered this at Tribeca - why or why not? Biggest differences between NYC tech vs Bay Area Tech COVID is causing many people to move away from the city. Any concerns about losing tech talent? How much does the exit environment for tech companies effects what you invest in? what's most undervalued in the public market or exit market at large that will be more appropriately valued in 3-5 years from now What's your take SPACs? 10/9 Brain's Tweet: "New 🦄 every 3 days this year vs. how many SPACs? Unicorns and SPACs are like pizza. If the ratio of cheese to sauce is off the 🍕 tastes bad and goes down poorly." What's your take on rolling funds?

On this special segment of The Full Ratchet, the following Investors are featured: Janet Bannister Shawn Carolan Reid Christian Villi Iltchev Each investor highlights a situation where they decided not to invest, why they passed, and how it played out.

Simeon Iheagwam of Noemis Ventures joins Nick to discuss Starting a Fund w/ Life Savings, Why it Takes More than Just Performance to Find Success, and Sticking to Your Framework. In this episode, we cover: Walk us through your background and path to VC What's the thesis at NOEMIS Ventures? What is your process for investing? Are there any must-haves? Like Brad Feld... you are syndication agnostic... don't care about who else is in the round and you're willing to be the first yes. How do you get to conviction -- especially not having worked for a large VC fund? Where do you help your portfolio companies the most? In your words... why is it difficult to launch a fund as a diverse manager? What were some of the most unexpected and challenging aspects of launching a fund? Strangest question you've received from an LP? What's your approach to investing in diverse founders? You were recently highlighted by Grasshopper Bank and Left Tackle Capital as an extraordinary funder. And I believe you joined their inaugural cohort called the Future Funders Institute? We've seen a few different accelerator-like programs spin up, targeted at emerging GPs. Tell us a bit about the program. 3 data points... Let's say you are approached to invest in a Fintech SaaS business with $5k MRR, and 20% MoM growth for the last 3 months. The 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: Stephen McIntyre Gigi Levy Weiss Richard Kerby Kane Hsieh Each investor discusses a portfolio company that did not survive and why it was that they failed.

Charles Adler of Kickstarter joins Nick to discuss The Founding Story of Kickstarter — Community, Competition, and Customer-Obsession. In this episode, we cover: Walk us through your background and path to tech. Growing up what inspired you most? How did the idea for Kickstarter begin? Was there an MVP - was there an initial target vertical? When did you know that it was working? What was the biggest mistake you made during the journey? When competition arose... did it scare you? Is Kickstarter today still delivering on the initial vision you and your co-founders had? What was the hardest part of growing a venture-backed company? What advice would you have for founders before selecting VC partners? Organic growth and categories? We often talk on the show about the importance of customer obsession, really knowing what they care about and spending time to understand that -- what has been your philosophy and approach w/ customers? Many founders and investors talk about the importance of diversity. We talk about the importance of climate change and the environment. We campaign for socio-economic equality. How do you think founders (and investors) can be more intentional about building their beliefs into their business and their culture? What are you focused on now... tell us about Lost Arts? Why do it alone? Community has been a common thread/focus across many of your efforts. Is community core to everything you do... if so why?

On this special segment of The Full Ratchet, the following Investors are featured: Ben Casnocha Janet Bannister Nikhil Basu Trivedi Farooq Abbasi Each investor describes the most unusual situation or pitch that they've encountered as an investor.

Guest Update: When the episode was recorded in 2019, Cyan was a partner at Founders Fund. Currently, Cyan is a partner at Long Journey Ventures. In this special replay of episode 180, Cyan Banister of Long Journey Ventures joins Nick to discuss the Self-Made Engineer, Angel, and Venture Capitalist. In this episode, we cover: So, Cyan you have a really interesting story and background that led you to where you are today. Feel free to start wherever makes most sense but can you talk about your life experience and how it led you to where you're at now? You spoke publicly about your early life at the 2018 TechCrunch Disrupt conference, from living on the streets to becoming a venture capitalist, tell us about this incredible journey, what you accredit your success to and how it lead to venture? Where along the way did you meet Scott? Did you guys every consider raising your own fund? How early are you able to go at Founder's Fund? How do you work with founders post-investment? Judicious with your magic bullets? Have you funded founders with non-traditional backgrounds or missions dedicated to folks living in poverty or providing access to upward mobility? How has your approach changed from your time as an angel to now your experience as a VC ? Do you have any good stories or learnings from Naval? Prior to FF you were an early stage investor in successful companies like Uber, Postmates, PayPal at others... I know you invest alongside Scott... who started angel investing? What was your early approach to angel investing and how were you able to source and select such iconic tech companies at very early stages? Can you tell us a bit about Founder's Fund and your focus? Stage, Sectors, Geographies? "The most promising companies tend to share a few characteristics: They are not popular. They are difficult to assess. They have technology risk, but not insurmountable technology risk. If they succeed, their technology will be extraordinarily valuable. We have no idea what these companies might look like, only that they probably will share these characteristics. Entrepreneurs often know better than we do what might be enormously valuable in the future." -- It's a very humble approach and one that resonates with me and many others. Can you elaborate on the thesis and characteristics of founders that are the best fit for Founders Fund? What's your take on the prevalent number of VCs that remove CEOs of their portfolio companies, on average, within three years of investment? What's your take on contrarian vs. conformist investing... first, how do you even determine what is contrarian and then what's your take on how each ties to performance?

In this special replay of episode 135 & 136, Eric Paley of Founder Collective joins Nick to dispel some conventional wisdom in VC. We address questions including: What's the focus at Founder Collective? What are the downsides of heavily funded companies? Overview and Methodology of the study of 71 IPOs: 'Overdosing on VC: Lessons from 71 IPOs' Conventional VC...

On this special segment of The Full Ratchet, the following Investors are featured: Eric Collins Trae Vassallo Ramy Adeeb M.G. Siegler Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach.

On this special segment of The Full Ratchet, the following individuals are featured: Nick Moran Thomas Gentle This will be a unique segment where, Founder of Shotcall, Thomas Gentle, will discuss his startup story and how he chose New Stack to participate in the funding round. follow us on Twitter @TheFullRatchet for updates and more information.

On this special segment of The Full Ratchet, the following Investors are featured: Check Warner Henrique Dubugras James Currier Lanham Napier Each investor discusses sectors, drivers and/or trends that may have a significant impact in the future and are potentially positioned for outsized-returns.

Avichal Garg of Electric Capital joins Nick to discuss The Intersection of Crypto and VC and the Future of Digital Currency. In this episode, we cover: Walk us through your background and path to VC What's the thesis at Electric Capital? How does the crypto focus change the fund structure of Electric Capital? When you invest capital and receive equity and/or coins in return... What determines that breakdown? For pure coin investments, how do you think about and manage liquidity and transactions over time? What are some of the big differences between traditional tech investing and crypto investing? How are the founder's different? What's are the biggest risk factors that are unique for early-stage cryptocurrencies?

On this special segment of The Full Ratchet, the following Investors are featured: Jason Whitney Leah Solivan Jim Douglass Elizabeth Yin Each investor highlights a situation where they decided not to invest, why they passed, and how it played out.

Lolita Taub & Jesse Middleton of The Community Fund join Nick to discuss The Fund that Started on Twitter, Why Community-driven Startups Win, and Embracing the Underestimated. In this episode, we cover: Background of Lolita & Jesse How did the two of you meet and ultimately decide to launch a fund together? What's the thesis at the Community Fund? Conflicts or issues running multiple funds that invest at similar stages? Why did you create a distributed investment team of 13? How did you select them? Approach to investing in cold reach outs? How does decision-making work? What does a great founder look like to you? You invest in community-driven companies... what does that mean, and how do you define community-driven?

On this special segment of The Full Ratchet, the following Investors are featured: Niki Pezeshki Somesh Dash Byron Deeter Trae Vassallo Each investor discusses a portfolio company that did not survive and why it was that they failed.

Reid Christian of CRV joins Nick to discuss Developer Tools, The Surge of European Tech, and Why Founder Needs Differ Across Regions. In this episode, we cover: Walk us through your background and path to VC What's the thesis at CRV? $600M closed in July... any change to approach or thesis? What are some of the focus areas that you're leaning into amidst the circumstances? How do you evaluate teams? What type of founders excites you to invest? Centralization — the shift from consumers to creators Why is your focus on SAAS/CLOUD/ENTERPRISE IT/BIG DATA? What does the future look like for Enterprise SaaS companies? How has your sourcing of startups changed? In another lifetime, would you like to be a professional basketball player or a venture capitalist? Three data points question

On this special segment of The Full Ratchet, the following Investors are featured: Erik Torenberg Ryan Gembala Jaclyn Hester Jonathan Hsu Each investor describes the most unusual situation or pitch that they've encountered as an investor.

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.

Eric Collins of Impact X Capital joins Nick to discuss The Changing "Search Image" of Founders, Lack of Diversity = Missed Opportunity, and COVID Effects on the BLM Movement in Europe. In this episode, we cover: Walk us through your background and path to VC What's the thesis at Impact X? As a black CEO and fund manager, in what ways do you think your experience fundraising was different than your white, male peers at other firms? How do you approach sourcing? What's unique about the way you've built your network vs. other firms? Less than 1% of venture funding goes to black-led and we've heard the tired line that "not enough companies are founded by underrepresented founders and black founders"... Are you concerned that you'll have fewer deals or less pipeline? What's the right number of deals per year where you feel like you're seeing a sufficient amount? I've heard about the "deep analysis" you do and how that creates the edge. Can you describe what this entails? Do the issues run deeper in the LP community than even the GP community? Are the return expectations different for your LPs vs. a non-Impact fund? A lot of the impact you are creating is long-term in nature. What are the leading indicators of success for your fund? How do you set objectives and measures to know if you're winning/exceeding the plan? In response to the pandemic, the gov't created a number of programs to help fast-growth companies. What was the impact on your underrepresented pipeline and portfolio? Black Lives Matter has been the center of attention here in the states. What's the status of the movement in the UK and how has it impacted your efforts at Impact X?

On this special segment of The Full Ratchet, the following Investors are featured: Richard Kerby Jaclyn Hester Lanham Napier Steve Blank Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach.

Erik Torenberg of Village Global joins Nick to discuss Decentralization of VC, Why Your Fund Size is Your Strategy, and Why Startup Formation is the Most Important Contributor to Economic Growth. In this episode, we cover: Walk us through your background and path to VC What were the biggest lessons learned from Product Hunt that you took to investing? Recently had Ben Casnocha on... anything specific you'd like to add about the thesis behind Village Global? How do you think about working with experienced vs non-experienced angels? How do you think about portfolio construction for VG? Fast forward... some angels have strong early signals of success, others don't -- do you cull the herd or amplify those that are good pickers? Considering this, why do you think so many VCs have concentrated portfolios? How do you think about follow on investing? What is the role of a pre-seed firm? If there's a weakness in the Village model... what is it? Part of your model is to increase the amount of founders and investors. What do you say to those that argue there's too much capital already? What's does the future look like for Venture? What's your advice for people getting into venture? Three data points Let's say you're approached to invest in an early seed stage SaaS startup... The founder is a technical serial entrepreneur with two solid 8-figure exits. And she has a credible co-founder that is more business/commercially focused; An MVP of the product has been launched and was the top product of the day on Product Hunt, when it launched; and The Product launched two months ago and currently has $5k of MRR. The 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: Jonathan Hsu John Vrionis Trae Vassallo Kane Hsieh Each investor discusses sectors, drivers, and/or trends that may have a significant impact in the future and are potentially positioned for outsized-returns.

Farooq Abbasi of Preface Ventures joins Nick to discuss Funding the Misunderstood Technical Founder, Self Evaluation as a Solo Capitalist, and Capital to Underwrite R&D risk vs. S&M risk. In this episode, we cover: Walk us through your background and path to VC Why did you launch Preface? What's the thesis at Preface? How do you define enterprise/infrastructure frontier enterprise? What's most different about your approach? Are the businesses you fund created and ideated by the founders or is it a collaboration between you and the founders or do you take concepts and bring them to future founders? What's your approach to sourcing? Because your model is different and the founder profile is a bit different than most... in what unique ways do you provide value post-investment? You're a solo-capitalist... How do you evaluate yourself and keep some checks/balances on your decisions? Did you put together an LPAC -- if so how big is the group, how often do you meet and when/where do they help? Are you actively investing in open-source startups? What are your thoughts on the Bifurcation in the VC industry... capital underwriting of R&D risk vs. S&M risk? What are your thoughts on biases in founder selection, data-driven predictors of founder success? What's been the greatest challenge in your VC career and how have you overcome it? You're passionate about Diversity, having founded Diversity.vc in 2016. How are you practicing a more inclusive style of venture capital? Three data points... hypothetical investment scenario

On this special segment of The Full Ratchet, the following Investors are featured: Darren Bechtel Melody Koh Somesh Dash Jeff Fluhr Each investor highlights a situation where they decided not to invest, why they passed, and how it played out.

Ty Findley of Ironspring joins Nick to discuss Industrial Innovation, Where Blitzscaling Doesn't Work, Why Sector Focus Wins, and Beginning with the End in Mind. In this episode, we cover: Walk us through your background and path to VC? Why the decision to leave Pritzker and become an MP at Ironspring? What's the thesis at Ironspring? Lots' of new firms and new funds being launched… How is Ironspring different? You're a "sector-focused" fund… why do you think specialized funds will outperform their generalist counterparts? We work in an asset class that often promotes bliztscaling, exponential growth and often spending ahead of progress… how do you rationalize the expectations of startups in our industry with the much slower pace that many legacy and heavy industrial industries… that your startups are serving… are going to move at? Glacial pace has benefits… long-term durability of cash flows, customer retention, pricing power… the moat Do you think product-led growth can work in these sectors? Talk about the difference between "occupations" vs. "activities" and why this is especially relevant in industrials amidst the pandemic? How do you think your style as an investor differs most from others (ie. discussion of decision making process/thinking in bets… focus on the decision not the outcome) How would you describe your system for investment decision making? 4-part framework of the "Day in the life of a VC fund manager"? Must-haves for an investment? Aligned with your recent collaboration on the article, "Evaluating the Successful Industrial Technology Exits", you've talked about startups in industrial tech "beginning with the end in mind"… why is this important? Rumor has it you're starting a podcast -- lots of new podcasts these days, why will your's standout and what's the objective?

On this special segment of The Full Ratchet, the following Investors are featured: Minnie Ingersoll Jim Douglass M.G. Siegler James Currier Each investor discusses a portfolio company that did not survive and why it was that they failed.

Lo Toney of Plexo Capital joins Nick to discuss Common Traits Shared by Top GPs, Why Underrepresented Fund Managers Will Produce Superior Returns, and SPACs vs. Direct Listings vs. IPOs. In this episode, we cover: Walk us through your background and path to VC? Why are Product Management skills similar to the skills required for VC? What's the thesis at Plexo Capital? Do you think a thesis on investing in underrepresented founders will produce superior returns? What do you say to pundits that claim you've restricted your options and will have far fewer managers to choose from... which will adversely impact returns? On a percentage basis... will there be more outsided outcomes from diverse founders (or managers) vs. those that are not diverse? How are you innovating on the LP side? We talked about some of the challenges of raising funds... are there ways that you work with and help emerging managers raising a first-time fund? Not just about performance... especially early on. What are the common success traits you see in GPs? What's your position on investing in the management company or even the GP itself? Where do you see the market for secondaries evolving? I'd like to talk about the exit market a bit... What are your thoughts on companies listing direct? How about the explosion of SPACs -- net positive or negative for venture? Any unintended consequences that founders (or investors) need to watch out for? Zoom is now worth more than Uber, Airbnb, and Stripe combined... Are the three companies undervalued or is Zoom overvalued... or is the pricing about right? Amazing to see companies like Paypal and Square have surpassed Goldman in market cap "3 Data Points"... You're approached by a first-time fund manager. The fund manager did not work for a large, brand-name venture firm before and she has never had an institutional investor. She has been actively investing for 3+ years. She plans to raise $20M to invest in 30 seed-stage companies w/ no reserves. The catch is you can only ask 3 questions (for 3 additional data points) to make your decision. What 3 questions do you ask?

On this special segment of The Full Ratchet, the following Investors are featured: Elizabeth Yin Michael Cardamone Gigi Levy-Weiss Niki Pezeshki Each investor describes the most unusual situation or pitch that they've encountered as an investor.

Lanham Napier of BuildGroup joins Nick to discuss Scaling Rackspace, The Evolving Responsibilities of a Venture-Backed CEO, and Confronting Big Tech Monopolies. In this episode, we cover: You took on capital from Seqouia, Norwest and others while at Rackspace. What was the biggest challenge to taking on venture capital? How were you able to move from the early product-market-fit days to true scale... what were the defining decisions/actions that helped you expand exponentially? As a company leaves the product-market-fit stage and reaches scale, what is the job of the CEO or how does the job of the CEO change as the company scales? You've talked about investing "long-term capital"... what do you mean by that? How have you created a fee-light model, where management fees are eliminated? How do you guide CEOs that have been conditioned to think in 12-18 months cycles, when the long-game is much more critical? You've hired and developed a lot of folks over the years. What advice do you have for young CEOs with regards to selection and/or development of people? Leadership -- great ones emerge in hard times. What are some of the most important lessons you've learned about leadership? We're in an environment where the largest tech companies have monopolized a lot of the upside in the market. Of course recently many of the CEOs appeared in front the house judiciary committee. Where do you stand on the position of large tech companies and how that impacts emerging startups? Do you think China is a threat to the U.S.'s position as world power and tech leader? What would suggest we do about it?

On this special segment of The Full Ratchet, the following Investors are featured: Henrique Dubugras Ryan Gembala Grace Isford Scott Kupor Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach.