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

Ash Rust of Sterling Road joins Nick to discuss "Blessed" Teams, Pseudo Deal Leads, and Caps at Pre vs Post. In this episode, we cover: His beginnings in tech and how that led to starting the fund What's the investment thesis at Sterling Road? What's unique about your approach that other firms aren't doing? Something that I think is frustrating for many founders is seeing these idealistic stories of founders that are raising $5M on a $20M cap with zero traction. And, it's also misleading in that I have a number of founders that think they need to be raising a lot more than they are... very early on before indications of product fit or even a focused commercial plan. Can you talk about the profile of these teams that are able to raise seemingly irrational seed rounds and then later let's jump into consequences. The seed round has now divided into a series of phases... we have pre-seed, seed, mango seed, seed+, seed exensions, etc. We've spoken to Semil Shah about this and how it's no longer a stage it's a series of phases and gates. Can you talk about these phases and how founders should think about milestones and raise amounts prior to raising an A? At New Stack we've encountered some strange and troubling circumstances regarding who the lead investor is on a deal and who is not. What are you seeing in terms of who takes the lead and how has that evolved over the past few years? Pro Rata has always been a hot button issue, for a variety of reasons and we're seeing some new challenges emerge as our portcos are raising up-rounds. What are the key issues you're observing with pro rata and what's your opinion on how it should be handled? A number of my founders are either raising more in their seed round or trying to pull-in and raise their A rounds before their ready b/c everyone is sounding the alarms about an impending recession... raise the money now, before it dries up. This seems curious and a bit misleading from my standpoint... What are your thoughts on founders raising more money or raising sooner because of a potential recession? I've been getting a number of pitch decks from so-called "CFOs" at startups... yet, upon review of a LinkedIN profile, it's pretty clear that these folks are bankers. Are you seeing the same and what are your thoughts? I think it was about eight months ago that YC changed its SAFE to a post-money cap, instead of a pre-money cap. They claimed to have the right intentions when they made the switch but we were immediately suspect for a few obvious reasons, some less so. Talk about about SAFEs as an investment instrument and your thoughts on the switch to post money caps. 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: Cyan Banister David Cohen John Fein Each investor highlights a situation where they decided not to invest, why they passed, and how it played out. 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.

Aydin Senkut of Felicis Ventures joins Nick to discuss Iconic Companies, Frontier Markets & a Truly Founder Centric Approach. In this episode, we cover: Backstory / Path to tech in SF? Prior to founding Felicis Ventures, you were a Product Manager at Google, launching their first 10 international sites, its first online search licensing products, and its first Safe Search…talk about what lead to your transition to investing. What's the story behind founding Felicis Ventures? Talk about the investment focus and approach of your firm. It states on the firms website that you back founders looking to open up frontier markets, such as longevity and engineered foods, and reinvent critical markets such as mental health and insurance….what are some of the success factors you've observed in startups trying to create or reinvent markets. You've invested in many iconic companies that have revolutionized their industry such as Shopify, Fitbit and CreditKarma, when investing at early stages, how do you differentiate between the ideas or trends that are going to have this long term affect from the ones that may not be so successful? Felicis states on the site that "The difference between a good product and a great product is one incalculably better than the current alternative. Successful founders have laser sharp focus on true product differentiation, intelligent time and capital allocation" Help us understand what seperates good product from great product. Differences in investing in domestic vs. international startups? You do this survey every year of your portfolio companies... can you talk about the key insights you've learned from doing that? 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: Rebecca Kaden Roy Bahat Elizabeth Galbut Each investor discusses a portfolio company that did not survive and why it was that they failed. 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.

Adeyemi Ajao of Base 10 Partners joins Nick to discuss Automation vs. AI. In this episode, we cover: Backstory - Growing up in Spain and Nigeria and his path to entrepreneurship. Previous to Base10 Partners, you had quite a successful career as an entrepreneur, founding highly influential companies such as Tuenti, Identified and Cabify in Latin America - talk a bit about your experience founding and scaling multiple tech companies, ultimately to exit? How did you, TJ and Reggie come together and decide to create Base10? On the website it says that you "started Base10 to take a profoundly different approach to Automation." Tell us more about your thesis on automation and how it's different. Talk about Automation vs. AI and the potentially misleading guidance that we're hearing from many firms in the valley with regard to AI. Of course, with any big changes that are made to the way people traditionally do things, there is a reaction. While some will embrace automation tools, others will have an adverse reaction. Are there certain sectors, categories or even functions that you think will more readily adopt automation solutions? You mentioned a number of industries... Real Estate, Construction, SaaS, Agriculture, Logistics, Consumer... you have these Partners listed on the website, like Fifth Wall, Bessemer, Owl, Shasta, Bain Capital... can you explain the details of your partnership program? When researching sectors that you're interested in and assessing the opportunity to implement automation tools, what key factors are you looking for? "We know automation. We have seen it succeed and fail. We know what playbook to apply from team structure to go-to-market, automated customer service or data collection systems." Talk to us about the playbook elements that have application across the automation-focused startups you work with? You've discussed the pride you take in being: Hispanic, American, European, African, black and white. It's quite notable that you raised the first black-led VC fund of over $100M. How were able to break through such a significant glass ceiling where others haven't? 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: Evangelos Simoudis Cheryl Cheng Wayne Kimmel Each investor describes the most unusual situation or pitch that they've encountered as an investor. 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.

Jeff Clavier of Uncork Capital joins Nick to discuss Market Cycles, Escalating Costs to Start Up, and the Micro VC Surge. In this episode, we cover: In 2004 you started making angel investments in emerging Web 2.0 companies and at that time, only a handful of individuals backed entrepreneurs in the internet space…What was your first investment and how did you get involved in the space? What's the story of the founding of SoftTech--now known as Uncork Capital. What led to the rebrand from SoftTech to Uncork? The investment focus/thesis of Uncork. You mentioned...FitBit, EventBrite, and Sendgrid...it's striking how different each of these businesses are...How you are able to get conviction and understand key success factors across different sectors with different models and overall profiles? How have the market cycles affected VC, your fund strategy, raising capital and the impact on portfolio companies? What are the most common mistakes you see early investors making? With the 600+ micro-VC funds now...is the stage over capitalized? Is it more expensive to build a startup today than 10 years ago? Being that you are from France...in your estimation, what have been the primary differences in funding European based startups vs. those in the States? Said to be one of the most helpful investors in the valley... what are some of the specific ways you get involved? On the firms website it talks about your "No Playbook" and "No Bullshit" approach that you're not delivering "prescriptive formulas on how to build or scale" but instead developing custom plans, one on one. Tell us about these custom plans and the key elements. How Jeff balances time and energy with so many portfolio companies.

On this special segment of The Full Ratchet, the following Investors are featured: SC Moatti Brendan Wallace Vic Pascucci Each investor illustrates a critical lesson learned about startup investing and how it's changed their approach. 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.

Welcome back to TFR for another Cram Session. In these special releases, we have aggregated the takeaways and tips from previous episodes. In this installment, we will be recapping the following episodes: 130. How Amazon, Fitbit & Snap Won; Where Apple, Pebble & Google Did Not, Part 1 (Ben Einstein) 131. How Amazon, Fitbit & Snap Won; Where Apple, Pebble & Google Did Not, Part 2 (Ben Einstein) 133. The Importance of Storytelling, VC EQ, and the LP-GP Dating Game, Part 1 (James R. 'Trey' Hart III) 134. The Importance of Storytelling, VC EQ, and the LP-GP Dating Game, Part 2 (James R. 'Trey' Hart III) 135. Dispelling Conventional Wisdom in VC, Part 1 | Does Capital Drive Outcomes? (Eric Paley) 136. Dispelling Conventional Wisdom in VC, Part 2 | Should Seed Investors Follow-on? (Eric Paley) 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: Jim Tananbaum John Fein Sarah Anderson Each investor discusses sectors, drivers and/or trends that may have significant impact in the future and are potentially positioned for outsized-returns. 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.