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The Road Untraveled: VC Perspectives with Brian Hollins

The Road Untraveled: VC Perspectives with Brian Hollins

By Brian Hollins

Most venture capital firms are stress testing the technology and hard hitting questions of what "tomorrow" may look like. Here’s their real-time take…
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Costanoa Ventures: Amy Cheetham on transitioning from Operating to Investing, building a venture partnership, and the role of hiring in scaling early startups

The Road Untraveled: VC Perspectives with Brian HollinsNov 30, 2023

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30:49
Costanoa Ventures: Amy Cheetham on transitioning from Operating to Investing, building a venture partnership, and the role of hiring in scaling early startups

Costanoa Ventures: Amy Cheetham on transitioning from Operating to Investing, building a venture partnership, and the role of hiring in scaling early startups

"I firmly believe that for-profit technology companies stand the best chance of solving many of the world’s toughest problems and venture lets me be a part of that process."


Amy is a Partner at Costanoa Ventures where she focuses primarily on fintech. In addition to deepening the firm’s fintech portfolio in the US, Amy has driven the firm’s expansion into emerging markets, specifically into Latin America and Africa. Her primary focus is on seed and series A stage B2B fintech companies, which encompass everything from fintech infrastructure to payments to application-layer tools. She has led multiple investments, including Assis, Malga, Highline, and Highnote.


Before joining Costanoa in 2019, Amy ran North American sales strategy and operations at Zuora, a public enterprise software company. Prior to that, she spent three years investing in growth stage technology companies at Summit Partners, where her investments included Podium, InfoArmor (acq. AllState), and onXmaps. Amy began her career on Wall Street, working at JP Morgan where she spent time as a technology investment banker and as an equities trader focused on financial services.

Nov 30, 202330:49
Lerer Hippeau's Ben Lerer on the rise of the NY Venture scene, building and scaling a firm, and building moats at the seed stage.

Lerer Hippeau's Ben Lerer on the rise of the NY Venture scene, building and scaling a firm, and building moats at the seed stage.

Ben Lerer is a Managing Partner at Lerer Hippeau. He is the Co-Founder and former CEO of Thrillist, which was acquired by Vox Media in 2022. He chairs the Board of Directors for Urban Upbound and is an Associate Member of the International Academy of Digital Arts & Sciences (IADAS).

Lerer holds a BS from the University of Pennsylvania.

Oct 23, 202337:44
From YC Hype to Data Moat Strategies: An Interview with Wen-Wen Lam, Partner at Gradient Ventures

From YC Hype to Data Moat Strategies: An Interview with Wen-Wen Lam, Partner at Gradient Ventures

Wen-Wen is a Partner at Gradient Ventures.

Previously, Wen-Wen was the CEO & Co-founder of NexTravel (YCW15), a leading corporate travel solution that serviced thousands of customers like Lyft, Twilio, and Stripe. She grew the business to over $100M in annual sales before exiting to Travelperk in 2020. Prior to this, Wen-Wen worked with a number of startups in leadership roles. She started her career in tech at LinkedIn. She received her BA from UC Berkeley in Economics and her MBA from USC Marshall School of Business.

Aug 31, 202322:08
Halcyon | Driving Change While Doing Good with Kate Goodall

Halcyon | Driving Change While Doing Good with Kate Goodall

Kate Goodall (she/her) is the Co-Founder and CEO of Halcyon, an incubator for early-stage impact ventures. Since launching in 2014, Goodall has added an early-stage venture fund (of which she is co-managing director), an angel investing network, microloan fund, and a range of intensive programs, continually seeking to serve increasing numbers of entrepreneurs globally in more ways in order to solve the pressing social and environmental problems of our time.

In 2016, Goodall helped establish WE Capital, a consortium of leading businesswomen investing in and supporting women and women-led companies. In 2018, Goodall launched an international arts and dialogue festival, By the People, which ended in the pandemic. Goodall has served as juror at national and international social entrepreneurship competitions, like the Creator Awards, Pitch@Palace, and MIT Tech Review Innovator Europe & Latin America, and has helped select the 2021-2022 Class of White House Fellows under the Biden Administration. She was listed as DC Inno’s Fire Blazer, one of the Washington Business Journal’s Power 100, 40 Under 40, Women Who Mean Business, and Washington’s New Guard, Washingtonian’s 2017 Tech Titans, and Techweek 100 DC’s Talent Cultivators. Goodall has also received the Crittenton Leadership Award, is a Sorenson Global Impact Leader, and a member of YPO.

In a prior life, Goodall worked as a Maritime Archaeologist. She has 2 sons who keep her on her toes.

Jul 19, 202337:20
Visible Hands VC - Daniel Acheampong on Building the Future of Venture Capital

Visible Hands VC - Daniel Acheampong on Building the Future of Venture Capital

Daniel Acheampong, Founder, Visible Hands VC

Daniel was most recently an Entrepreneur in Resident at MIT designX, where he co-founded a marketplace platform. He was an associate at Summit Partners, where he helped manage the firm’s due diligence process to raise investment funds. Previously, he was a financial analyst at Goldman Sachs, where he supported senior management in supervising the New England Private Wealth Management business. He received a dual Masters in Business Administration from the Wharton School and Public Administration from Harvard Kennedy School. He received his Bachelor of Arts from Brandeis University.

He spends his free time trying new exercise routines, snacking on peanut trail mixes, and reading lots of non-fiction.

Jun 01, 202324:24
The Kings of LA: Ajay Relan on the Slauson & Co. Story

The Kings of LA: Ajay Relan on the Slauson & Co. Story

About Ajay:

Ajay Relan is an investor, entrepreneur, and community builder. Prior to Slauson & Co., Ajay was a founding Partner at Queensbridge Venture Partners. With a keen focus on brand building and storytelling, Ajay's passion lies in identifying trends and engineering culturally aligned brands.

A lifelong Angeleno, Ajay has established a business portfolio grounded in community. His most recent collaboration, Hilltop Coffee + Kitchen, has become a staple, facilitating productivity and collaboration in diverse neighborhoods across Los Angeles.

In 2012, Ajay founded #HashtagLunchbag, a grassroots movement that has fed 1,000,000+ hungry and unhoused people in 150+ cities around the globe. He went on to establish the Living Through Giving Foundation, a non-profit platform empowering the creation of programs engaging diverse groups of people to contribute to various causes in their local communities.

Ajay is a graduate of UC Santa Barbara.

Episode Highlights:

  • The power in your lived experience and how it can be used as a competitive advantage. 
  • When looking for founders, look for people who are delusional with their vision but pragmatic with their execution. Meaning you want to look for founders who are big dreamers with big goals but who also have a game plan, are focused and are willing to put in the work. 
  • Life is overwhelming, especially in the VC world, so take some time to create quiet in your life. 


Apr 12, 202325:47
"Bada** Woman" | The Chingona Ventures Journey with Samara Hernandez

"Bada** Woman" | The Chingona Ventures Journey with Samara Hernandez

About Samara: 

Samara Mejia Hernandez is the Founding Partner and Managing Director of Chingona Ventures, a Venture Fund that focuses on rapidly changing sectors and founders with experiences that uniquely position them to build startups in underserved growth markets.

The fund has $60MM in AUM and has made over 40 investments across technology sectors in Financial, Food, Future of Learning, and Health/Wellness. Before this, she was an investor at MATH Venture Partners, started her career at Goldman Sachs, and she is on the advisory boards for Coolwater, Camino Financial, and VentureFWD.


Episode Highlights: 

  • What it was like growing up in an immigrant family and how that environment of helping others and building community impacted her today
  • Tip for new firm builders - let relationships and mentorships happen organically, don’t force things but be proactive with your outreach and networking and then let it happen
  • Look for opportunities to build, and don't be so rigid in your journey. Demonstrate the qualities that would make a sponsor want to sponsor you
  • Tips for entrepreneurs; just get started!, don’t be afraid to fail, tap into your network and don’t be afraid to ask for help
Dec 28, 202223:47
The King of Twitter | Mac Conwell on Building Rarebreed Ventures

The King of Twitter | Mac Conwell on Building Rarebreed Ventures

Key takeaways:

--Your limit to opportunities is your own mindset. 

--Founders should build their network consistently over time. It will help you understand the fundraising journey, and bring you honest feedback about how long the journey will take.

--Early stage investors are "founder evaluators" more so than "business evaluators". Help them believe you have the network, skills, grit, intelligence and flexibility it takes to get you to the Series B and beyond.


Mac Concell - Rarebreed Ventures

Mckeever E. (Mac) Conwell, 2nd, is a Baltimore native and attended Morgan State University, majoring in Computer Science. In 2006 at the age of 19 he joined a co-op program with the Department of Defense where he achieved Top Secret Security Clearance. He went on to become a government contractor doing software development in multiple computer languages and working for several companies, including Northrop Grumman and Booz | Allen | Hamilton. In October of 2009 Mac co-founded his first tech startup, Given.to. The Given.to team successfully completed two accelerators, Accelerate Baltimore and NewMe Accelerator, where he was later named entrepreneur-in-residence. Mac and his team sold the technology in 2014. His next venture, RedBerry, was accepted into the Dreamit Ventures Accelerator in Philadelphia.

Mac has been a guest on Huffington Post Live several times and his companies have been featured in many media outlets such as USA Today, Washington Post, BET, CNN Headline News, and Black Enterprise. Brought on board at TEDCO in the newly-created role of Deal Team Coordinator, Mac is using all of the knowledge he has gained working for both public and private sectors. Mac is responsible for the coordination of all stages of new deals brought into TEDCO.


Nov 29, 202229:01
Chloe Capital's Elisa Miller-Out on lessons for leaders scaling a company, what its like on the investor side of the table, and a word of advice for the next gen of Founders.

Chloe Capital's Elisa Miller-Out on lessons for leaders scaling a company, what its like on the investor side of the table, and a word of advice for the next gen of Founders.

Elisa Miller-Out, Managing Partner

Elisa Miller-Out is Chloe Capital’s Co-Founder and Managing Partner. She is an experienced serial tech entrepreneur, having founded and led seven companies over 20+ years. She is an experienced investor, having invested in 45 companies, in addition to executing 10 M&A transactions. Elisa is also an active board director and community builder. As an Innovation Advisor at NYSERDA, she helps advise on an $800 Million portfolio of entrepreneurship and investment programs for climate tech startups. She also serves as a mentor and Entrepreneur in Residence with several organizations, including Cornell University’s Center for Regional Economic Advancement, Launch NY, 76West and others. In addition, Elisa is an instructor with the National Science Foundation Innovation Corps and a guest lecturer at Cornell and Columbia. Elisa serves as a board director at Dimensional Energy, Impact Makers, Switch and as chair of the board at Singlebrook, a custom software services firm Elisa co-founded and led as CEO for over 10 years. Elisa oversaw the successful acquisition of a division of the company in 2016. Elisa has been featured in the New York Times, the Washington Post, USA Today, Forbes and other publications, and she speaks about technology and entrepreneurship at events across the country. Elisa graduated Summa Cum Laude from Barnard College of Columbia University. Learn more at ElisaMillerOut.com.


Submit your company for future investment from Chloe Capital: chloecapital.com/funding

Oct 18, 202240:23
Eric Tarczynski from Contrary on: spotting Hyper-Growth, tips for first time builders and the impact of price compression at the early stage

Eric Tarczynski from Contrary on: spotting Hyper-Growth, tips for first time builders and the impact of price compression at the early stage

Eric is the founder and GP of Contrary. Contrary's portfolio includes hyper-growth companies like Anduril, Ramp, and Zepto.

Key Takeaways: 

  • Identify the brightest people in the world first, then build infrastructure to support them for their entire life
  • Identify LPs who believe in you emotionally before they believe in your model (not people in wealth preservation mode)
  • Price compression has not fully met seed stage, but it is likely coming and will likely land south of 20mm post at the seed stage
  • If you are starting a c company u need to have an edge and clarity of thought around why you are the perfect person to build it
Sep 15, 202229:26
Let's Talk Consumer! Redpoint Ventures' Meera Clark on thesis driven investing, spotting resilient founders and building your brand in venture

Let's Talk Consumer! Redpoint Ventures' Meera Clark on thesis driven investing, spotting resilient founders and building your brand in venture

Topics covered: 

  • Finding founders through thesis-driven investing
  • Spotting resilient founders- are they building because this product needs to exist
  • What this new market means for deal pacing
  • Driving value add for portfolio companies
  • The talent recruiting landscape
  • Building your brand in venture


About Meera: I’m an early stage investor at Redpoint Ventures passionate about empowering consumers to live their best lives -- be it personally or professionally.

Forbes 30 Under 30. Business Insider 55 Investors to Watch. Venture Forward Women in VC: Rising Stars to Watch. American Banker Powerful Women of the Future. All honors that pale in comparison to the privilege of backing founders focused on building a better tomorrow.

Related Rabbit Holes: All Raise Annual Summit Steering Committee, Stanford Professionals in Finance Board Director, Kauffman Fellow, and fan girl / daughter to a badass working mom :)

Tweets: https://www.twitter.com/itsmeeraclark
Musings: https://meeraclark.medium.com/

Jul 14, 202236:00
Startup Fundraising 101 with Nathan Beckord, CEO of Foundersuite

Startup Fundraising 101 with Nathan Beckord, CEO of Foundersuite

Nathan Beckord is the CEO of Foundersuite.com and VentureArchetypes.com. On the consulting and advisory side, he mainly works with early stage internet, B2B software, mobile, and consumer product startups. He is also interested in platforms, markets, and networks. Nathan has worked with several crowdfunding companies, such as Kickstarter and Appbackr. He is also the organizer of StartupBD.com and StartupExits.com.


Key Takeaways

  1. Start your fundraising journey long before you need the capital.
  2. Be thoughtful as you build "top of funnel" outreach. Build a highly qualified list of curated investors, and send a thoughtful email even if you don't have a warm intro.
  3. Investors should recognize that most founders are raising capital for the first time, and should support them in that journey with tips and tricks from years of seeing best practices (as opposed to assuming they know those things).



May 10, 202222:44
The SLOW Burn - Sam Lessin on thinking outside the box, investing in human potential, and what he has learned building Slow Ventures

The SLOW Burn - Sam Lessin on thinking outside the box, investing in human potential, and what he has learned building Slow Ventures

Sam Lessin - General Partner at Slow Ventures. He has co-founded two companies, Fin and Drop.io (acquired by Facebook in 2010). Between 2010 and 2014 Sam was a VP of product management at Facebook, where he managed the People, Places, and Things product group and the Identity product group. Sam started his career at Bain and Company and attended Harvard as part of the graduating class of 2005. 

Things we cover: 

  • Starting Slow Ventures and working with notable companies early on in their creation such as Birchbox, Venmo, and many more
  • Sam's unique funding ideology and the importance of building a thesis
  • The new Human Potential Initiative, in which Slow Ventures invests directly into individuals rather than their businesses
  • The passion factor that is needed when working with founders and startups 
  • Sam's opinion on investing in friends and working closely with people that you trust and respect
Apr 06, 202228:11
"It Takes a Village" - From Techstars to Launching The Fund with Jenny Fielding

"It Takes a Village" - From Techstars to Launching The Fund with Jenny Fielding

Jenny Feilding, General Partner at The Fund, Adjunct professor at Columbia, and entrepreneur joins us on the Road Untraveled this week. Jenny is a pre-seed investor and mentor to hundreds of founders around the world. She is a 2x entrepreneur herself and knows how challenging it is to build great products, inspire a team and keep the lights on. She has helped start-ups such as Latch (LTCH), Chainalysis, Tempo Automation, Alloy, Headway, Supergreat, and many more. 


Key Takeaways: 

  • The best investors focus on building community authentically and rolling up their sleeves to help mentor the next great entrepreneurs, VC's, and companies. 
  • The many to many model (in which a community of founders provides capital and mentorship to a group of entrepreneurs) is more effective than the one to many traditional VC model. 
  • "If you're going to raise venture capital, that is not a solo activity, it takes a village to do that. And so having more connectivity to other founders and to people in the ecosystem I think is really what helps get the momentum going".
Mar 23, 202224:47
Hunter Walk (Homebrew) - The Screendoor Initiative, lessons learned in big tech, & how to enjoy the journey
Mar 09, 202232:36
The RAISE Conference - Talking LP/GP relationships with Ben Black (Akkadian Ventures)

The RAISE Conference - Talking LP/GP relationships with Ben Black (Akkadian Ventures)

Key Take-Aways

Ben Black - Founder and CEO of Akkadian Ventures:

1. "Venture capital requires a level of trust that is unlike any other business because you find out your failures first before you figure out your wins. And if you want to press personal relationships and really put a lot of pressure on them, deal with failure together."

2. Tune out the noise of others and focus inward before looking towards others for validation.

3. Starting and building a well known conference can be a lot of work, but it is a powerful way to build community and bring people together around a cause. 

Feb 22, 202223:09
David Fialkow (General Catalyst) - Helping founders communicate in tough times, building diverse investment teams and what it takes to win.

David Fialkow (General Catalyst) - Helping founders communicate in tough times, building diverse investment teams and what it takes to win.

I had an insightful conversation with David Fialkow, Co-founder and Managing Director of General Catalyst, a venture capital firm that partners with founders from seed to growth stage to build companies that withstand the test of time. 


Key Take-Aways From This Episode: 

1. David speaks about the importance of connection and the value of working with his partner Joel Cutler to build General Catalyst as a team.

2. The value of creating a space for diversity in investment through making a choice to prioritize bringing in different opinions, different views, and different backgrounds in leadership teams.

3. David shares real-world knowledge on the importance of strong leadership teams when building both VC firms and also businesses

Feb 08, 202228:39
Lightspeed Venture Partners - Barry Eggers on building a global venture brand, navigating LP relationships for emerging managers, and the Lightspeed Scout Fund.

Lightspeed Venture Partners - Barry Eggers on building a global venture brand, navigating LP relationships for emerging managers, and the Lightspeed Scout Fund.

On today's episode, I am joined by Barry Eggers, Founding Partner at Lightspeed Venture Partners.


Episode Key Takeaways: 

  • Barry shares with us his 20+ year journey from a new venture firm in the early 2000s to the global powerhouse that is Lightspeed today.


  • We get Barrys take on the state of venture and his position on acknowledging and preparing for the ups and downs that come with being in the industry.


  • He gives helpful tips on how to navigate relationships with your LPs for emerging managers.


  • We learn about Lightspead's Scout program, which has a mission to offer VC investing opportunities to racial minorities in an effort to diversify VC and find unique entrepreneurs from around the world. 
Jan 26, 202231:06
Navigating Your Fundraise Journey with Jean-Pierre Adechi, CEO at Wheeli

Navigating Your Fundraise Journey with Jean-Pierre Adechi, CEO at Wheeli

Jean-Pierre Adechi, Founder & CEO, Wheeli

Key Takeaways

1. The system isn't merit based- build relationships and a network that can help you build trust in the communities that will allow you to access the resources you need to succeed 

2. Lean on advisors and people from the community to better identify folks who want to help you navigate the system

3. Be clear about your ask and be direct when looking for help from people

For more information: jpadechi.com

Jul 20, 202128:35
The Godfather of Pre-seed Investing: A Conversation with Charles Hudson of Precursor Ventures

The Godfather of Pre-seed Investing: A Conversation with Charles Hudson of Precursor Ventures

Charles Hudson is Founder and Managing Partner at Precursor Ventures

Key Takeaways:

1. Volume matters- do you get to meet enough companies in a year. They meet 3-4k companies and make 30 investments. You can't identify high quality founders if you don't see enough of them.

2. Some investors are great product people, some are good at market structure, some are good people pickers. It helps in venture to decide where you are strongest and double down into it.

3. However much time you're spending on portfolio construction, spend twice as much. LPs care deeply about fund construction and what it takes to build a thoughtful portfolio.

4. When fundraising, look for people who give reciprocal energy, and spend time with them. When you get no follow up, no engagement, don't chase people and instead spend that energy on other folks that care.

Apr 29, 202137:09
Mercedes Bent (Lightspeed Venture Partners) on the future of edtech, how exceptional founders prioritize, and the need for more diverse VC investors.

Mercedes Bent (Lightspeed Venture Partners) on the future of edtech, how exceptional founders prioritize, and the need for more diverse VC investors.

Key Takeaways

1. Exceptional founders understand "what matters most". They help triage what is most important and help their teams deliver on the priorities that matter most for the growth of the business.

2. Founders must be "learning animals"- ready to scale and upskill at all times. They must surround themselves with smart talent, ask questions, and practice maintaining self-awareness.

3. Edtech trends- lots of strong competition in learning, onboarding, etc. but one underinvested ecosystem is the outplacement and transition segment. This while complete the loop within edtech, and we should expect to see more companies come out of there soon. 

4. VC diversity- Organizations like BLCKVC are paving the way for new diverse entrants to the ecosystem, but senior leadership of Firm's must be committed to changing the composition of their teams in order for diversity to grow and be long lasting within a company.


Mar 16, 202131:20
Kauffman Fellowship - Jeff Harbach on finding your "zone of genius", advice for emerging managers and his take on trends coming to the venture industry.

Kauffman Fellowship - Jeff Harbach on finding your "zone of genius", advice for emerging managers and his take on trends coming to the venture industry.

Jeff Harbach, President & CEO, Kauffman Fellows

Key Takeaways

  1. The worlds biggest problems will be solved by companies that weren't venture backable in the past. More importantly, the people building those companies will be the folks who have experiencing dealing with those problems first hand, and will likely be more representative of society (more diverse, younger, etc.).
  2. KFP builds an awareness around continuous learning and the importance of active listening.
  3. The best VCs are deeply authentic and they bring that authenticity to the table every day.
  4. Advice for Emerging Managers-figure out your why, embrace what makes you unique and stick with it.

In this episode we talk about the 4 Pillars For Success Jeff has spotted through his time leading Kauffman Fellows. To learn more about The Kauffman Fellows program, visit https://www.kauffmanfellows.org/

Jan 31, 202128:08
James Currier and Brittany Yoon (NFX) on Network Effects and the Power of Building Community

James Currier and Brittany Yoon (NFX) on Network Effects and the Power of Building Community

Key Takeaways:

1. 70% of the value in tech has been created by catalyzing network effects within the core business.

2. Competition in the venture ecosystem is good for business. The disbalance of power in the past caused bad behavior, and more competition is good for Founders and helps them find the best partner for their specific endeavor.

3. Look for Founder's who can take other peoples perspectives. A lot of Founders aren't self critical enough, and don't live in the shoes of the customer or investor or their employee enough, and the skill of seeing something as others see it allows you to be a better builder, mentor, negotiator and leader.

4. For folks breaking into venture, find a fund you can relate with and is in tune with your ethos. Also leverage your experience but recognize that it may be a bias, so spend time seeing things from multiple angles and learn from those around you.

Dec 10, 202028:20
David Tisch (Box Group) on investing with a prepared mind, finding the best teams and how to build a strong generalist portfolio.

David Tisch (Box Group) on investing with a prepared mind, finding the best teams and how to build a strong generalist portfolio.

David Tisch, Founder & Managing Partner, Box Group

Key Takeaways,

1) Behind every great company are people, and it's our job to identify the best teams and try to convince them to let us work with them. 

2) Friends give advice, parents tell people what to do. The best investors are friends, who prioritize Founder interest over their own.

3) The process of finding great companies never ends. You must commit to the focus of building concentric networks and diligently looking in places others aren't looking.

4) "`Don't ever short the future." It is hard to proactively identify the trends of the future, but showing up with a prepared mind before meeting Founders is the only way to be ready to fund and win the next big opportunity.

Nov 18, 202039:29
The Queen of Equal Pay: Leyla Seka (Operator Collective) on building coalition and community, identifying talented Founders, and tips as you prepare for your Fundraise.

The Queen of Equal Pay: Leyla Seka (Operator Collective) on building coalition and community, identifying talented Founders, and tips as you prepare for your Fundraise.

Leyla Seka, Partner, Operator Collective

Key Takeaways:

1) Build consensus within an organization and work in the background to gain momentum before asking for support. Bring in a holistic view and others opinions to make sure you are analyzing all the valid perspectives.

2) Come solution oriented when you are working to create change.

3) There's no finish line to equality work. The country is not equal, and I encourage people to take action and find ways to pave the path for those who come after us.

4) Identify complimentary skillsets to build effective teams and partnerships.

Oct 29, 202026:23
Clouded Judgement: SaaS trends, what it takes to go public, and how to build a personal brand with Jamin Ball (Redpoint Ventures)

Clouded Judgement: SaaS trends, what it takes to go public, and how to build a personal brand with Jamin Ball (Redpoint Ventures)

Jamin Ball, Redpoint Ventures

Key Takeaways:

1. Productivity tools, remote collaboration and cloud security are three areas seeing momentum due to the move to remote during the pandemic.

2. Net revenue retention and GM adjusted CAC Payback are two metrics he watches to see if a company has what it takes to succeed in public markets.

3. Don't underestimate the value of the day to day relationships and time spent with founders. Treat people with respect, and recognize that their feedback will impact your reputation.


Oct 20, 202030:06
Sequoia Scout Crystal Widjaja on the Sequoia investing framework, building consumer products and becoming a good seed investor.

Sequoia Scout Crystal Widjaja on the Sequoia investing framework, building consumer products and becoming a good seed investor.

Crystal Widjaja, Startup Advisor & Sequoia Scout

Key Takeaways:

1) Spending time operating before venture helps you better understand the drivers of growth in a company, and it's helpful when you sit on the other side because it helps you identify founders who really understand the journey.

2) As you begin scout investing, develop your thesis around team specific product experiences. Some teams may like a product in a way that other teams don't, and make sure the companies you are scouting understand which user to sell to for their product.

3) Look for tenacious founders that are looking to do the hardwork and truly understand what their users care about.
4) Check out www.generationgirl.org!!

Oct 07, 202025:25
Semil Shah (Haystack VC) on the LP landscape, advice for founders, and the "chocolate chip cookie company" fallacy

Semil Shah (Haystack VC) on the LP landscape, advice for founders, and the "chocolate chip cookie company" fallacy

Semil Shah, Managing Partner, Haystack VC

Key Takeaways:

1) LP's struggle to deploy capital without face to face opportunities, so emerging managers are not being funded as quickly as they hoped. On the flip side, many LP's are excited about the pending reset in asset prices from a downturn, and funding may pick up sooner than expected as they search for improved returns over the next decade.

2) The investors that are able to play offense through these times have triaged the portfolio effectively and are now focused on upside maximization.

3) COVID provides tailwinds, but many of these tailwinds are obvious in times like this (telemedicine, online education, collaboration software, etc). Funds should be careful before building a portfolio just off of the current times. 

Sep 09, 202023:45
'Back to School' with the Moore Twins (CRV) on breaking into venture, building a personal brand and sourcing great companies in a pandemic

'Back to School' with the Moore Twins (CRV) on breaking into venture, building a personal brand and sourcing great companies in a pandemic

Olivia and Justine Moore, CRV

Key Takeaways:

1. Sourcing: college students are often the first adopters of next gen consumer platforms, and being around the college campus is a great way to get involved.

2. Finding trends: follow a diverse range of creators outside of your friend community to see what new products and apps are gaining traction. 

3. Value add VCs: spending time with founders and asking what they need help with matters. The challenge in covid is that some companies have been wiped out and others are thriving as a result, so understanding which founders need what types of support is important. 

Aug 26, 202022:50
Courtside VC on the return of the NBA, the future of in game betting and the Stockdale Paradox.

Courtside VC on the return of the NBA, the future of in game betting and the Stockdale Paradox.

Courtside VC, Founding Partners (Vasu Kulkarni + Deepen Parikh)

Key takeaways:

1. Sports is a global gateway, and there is a lot of pent up demand for it. It's not a matter of if, but when, and there will be significant momentum when it can finally return.

2. 75% of betting in Europe is in game betting, while only 25% in the US. There is a lot of technology that goes into making that possible, and many of which will start taking off.

3. Nascent tech being tested and slow rolled over the past few years will be forced into adoption in the next few years to make up for lost revenue. 

Jul 30, 202025:51
645 Ventures' Nnamdi Okike on the top 5 myths of Billion dollar startups, leveraging data to find investments, "return the fund" frameworks, and advice for black founders.

645 Ventures' Nnamdi Okike on the top 5 myths of Billion dollar startups, leveraging data to find investments, "return the fund" frameworks, and advice for black founders.

Nnamdi Okike, Founder & Managing Partner, 645 Ventures

Key Takeaways:

1. Deals today can be more efficiently identified outside of the traditional technology hubs. In part because software companies today require less upfront capital, but also because and the technical talent needed to scale them is more distributed than ever before.

2. Founders should recognize whether their company (and category) are advantaged, disadvantaged or neutral as a result of covid.

3. Going forward teams will focus on the same unit economics, but put more emphasis on raising and maintaining sufficient cash runway to ensure they can achieve milestones before returning to the markets for fresh capital. 

Jul 16, 202024:55
NextView Ventures' Rob Go on investing in underrepresented Founders, the transition from FOMO to FOLD, and changes to the consumer business model.

NextView Ventures' Rob Go on investing in underrepresented Founders, the transition from FOMO to FOLD, and changes to the consumer business model.

Rob Go, General Partner, NextView Ventures

Key Takeaways:

1. E-com businesses that have subscription-like unit economics will begin to be treated more favorably as this crisis unlocks a new consistent consumer base.

2. Dislocation between economic realities and public markets exists, but early stage company valuations are still predominantly driven by their competition.

3. Reference checks are a critical and useful way to check on a founder in a remote environment.  


Jul 08, 202023:02
Brendan Wallace (Fifth Wall) on built world technology, the future of the retail ecosystem, and the impact of COVID on the home office setup.

Brendan Wallace (Fifth Wall) on built world technology, the future of the retail ecosystem, and the impact of COVID on the home office setup.

Brendan Wallace, Founder and Managing Partner, Fifth Wall

Key Takeaways: 

1. Emerging manager needs to be able to clearly articulate their edge in the market and what makes them win vs other new funds, especially in times where capital is harder to raise.

2. 90% of US retail still happens offline, and we don't know when they will open or how people will react when they do. Ecommerce has the opportunity to fundamentally shift the way we shop, and COVID has accelerated that adoption.

3. A greater portion of the workforce will want to work flexibly, and a greater portion of employers will allow it. Employees will need to have stronger home office setups, and there is an opportunity for technology companies to address this going forward.

Jun 30, 202022:08
Jules Maltz (IVP) with a note for aspiring VCs, the importance of protecting cash flow, and changes to the VC funding environment

Jules Maltz (IVP) with a note for aspiring VCs, the importance of protecting cash flow, and changes to the VC funding environment

Jules Maltz, General Partner, IVP

Key takeaways:

1. Companies don't go out of business because the idea fails, they go out of business because they run out of money. Protecting your resources allows you to pivot and weather the storm.

2. Building in "degrees of freedom" that allow the business to sustain revenue decline/downturns is critical and should be part of the scenario testing process.

3. For aspiring VCs, begin looking for investments now and building the skillset, there are some great companies being built and it is a great time to learn.

Jun 25, 202021:49
Legendary Investor Brad Feld (Foundry Group) on never having "fake days", how to be a better ally, the impact of second order effects, and the failure of warning systems in tech.

Legendary Investor Brad Feld (Foundry Group) on never having "fake days", how to be a better ally, the impact of second order effects, and the failure of warning systems in tech.

Key Takeaways:

1.  A great way to be a helpful ally is not to shift the burden and ask how you can help, but ask what programs and organizations they care about and donate your time and money to help those causes grow.

2. Warning systems fail because they don't tell us when they are no longer going to warn us. Whether within a company or out in society, all warning systems are only as reliant as the inputs they are built upon. 

3. Never have "fake days"- leaders should stop spending time on things that don't bring positive emotional value to them or positive economic impact to their business. 

Jun 15, 202045:34
Road Untraveled: 5-time Founder and General Partner Nihal Mehta (Eniac Ventures) on the media consumption trends, industries to watch, and building a company in a pandemic.

Road Untraveled: 5-time Founder and General Partner Nihal Mehta (Eniac Ventures) on the media consumption trends, industries to watch, and building a company in a pandemic.

Nihal Mehta, Founding General Partner, Eniac Ventures

Key Takeaways:

1. "Time spent on media" vs "ad dollars going to media" are not directly tied. Consumer business models are not designed to succeed in recessions, and many will need to adjust rapidly to survive.

2. Construction, real estate, insurance, health care are large components of GDP transforming very quickly, presenting new opportunities for investors.

3. It's a great time to build, but not a great time to sell. Spend time building and improving your product, as opposed to focusing on selling.

4. Customers and buyers are also facing tight budgets, and there are better uses of your team's energy and focus over the next 12 months.

May 23, 202017:35
Road Untraveled: Sheel Tyle (Amplo) on building companies that matter, false rallies in the stock market, and the perseverance of "downturn founders".

Road Untraveled: Sheel Tyle (Amplo) on building companies that matter, false rallies in the stock market, and the perseverance of "downturn founders".

Sheel Tyle, Founder and CEO, Amplo

Key Takeaways:

1. Public market run up is a result of investors struggling to find good places to deploy capital. Low interest rates and an increase in trading volumes can create false rallies, and don't necessarily suggest strong fundamentals.

2. Advice to Founders: Hope for the best and plan for the worst. 

3. Treat employees like partners, not commodities. Don't be afraid to share the rationale with your employees, and allow them to be a part of the journey.

4. The perseverance required to build during a downturn often leads to the creation of some of the greatest companies.

May 14, 202022:30
Road Untraveled: Miriam Rivera (Ulu Ventures) on advice to startup founders, the importance of investing in diverse teams, and the innovation that often arises in times of adversity.

Road Untraveled: Miriam Rivera (Ulu Ventures) on advice to startup founders, the importance of investing in diverse teams, and the innovation that often arises in times of adversity.

Miriam Rivera, Founder & Managing Partner, Ulu Ventures

Key Takeaways:

1. Role models and resources can change the trajectory of a student's professional journey. Find ways to take a chance on students who may not look like you, and drive the diversity you want to see in the World.

2. Founders should evaluate the spectrum of capital available when deciding to raise money. 

3. A renewed emphasis on survival, profitability and retention will help many companies be better positioned to succeed in the long run.

4. The venture investing life cycle is 10+ years, so many funds will maintain their long-term perspectives and continue working to identify the companies that will be category winners long term. 


May 12, 202028:09
Road Untraveled: (Sports) DRIVE by DraftKings - Managing Director Kiki Mills Johnston on returning to sports after COVID19 and the future of fan engagement.

Road Untraveled: (Sports) DRIVE by DraftKings - Managing Director Kiki Mills Johnston on returning to sports after COVID19 and the future of fan engagement.

Kiki Mills Johnston, Managing Director, DRIVE by DraftKings

Key takeaways:

1. Companies are trying to identify ways to engage fans when they aren't able to bring them into the stadium (VR, competitions, fantasy, etc)

2. A new light is being shed on e-sports, but we still need to ask "is this a means to an end or a new norm once all this settles".

3. Switch up your information sources to avoid information overload or only getting one sided perspectives.


May 10, 202012:56
Road Untraveled: Marlon Nichols from MaC Venture Capital on companies that thrive in this environment, the importance of still setting goals, and how to support diverse founders right now.

Road Untraveled: Marlon Nichols from MaC Venture Capital on companies that thrive in this environment, the importance of still setting goals, and how to support diverse founders right now.

Marlon Nichols, Founder & Managing Partner, MaC Venture Capital

Key Takeaways:

1. Companies that can thrive in this environment: health tech space, remote work, collaboration, government/reg tech.

2. Companies will have to make hard changes, but need to keep an eye on how the business is performing and whether you are still achieving the short term goals you set out to accomplish.

3.  Diverse founders are historically underfunded, but once funded, tend to outperform non-diverse teams by 30% on average. Investors should continue to find ways to source and support diverse teams much like the efforts of the 'Launch with GS' team.

May 04, 202020:25
Road Untraveled: M13's Courtney Reum on interesting consumer sectors to watch, the "experiential" economy, and the importance of wellness and self care.

Road Untraveled: M13's Courtney Reum on interesting consumer sectors to watch, the "experiential" economy, and the importance of wellness and self care.

Courtney Reum, Founder, M13

1. Double down on transparency and communication with your investors and employees.

2. Consumer companies will have to bridge the frustrations in delivery lag by creating unique messaging and a sense of community to capture customers.

3. Founders should think hard about how to not self-isolate during these lonely times. Expand your ecosystem, bring on founders and others to bounce ideas and share best practices.

Apr 29, 202018:44
Road Untraveled: Lightspeed Venture Partners' Amy Wu on the PPP program, cash flow management, and the industries she is watching.

Road Untraveled: Lightspeed Venture Partners' Amy Wu on the PPP program, cash flow management, and the industries she is watching.

Amy Wu, Partner, Lightspeed Venture Partners

Key Takeaways:

1. Teams should think about stress-testing for both "COVID impact" as well as "recession impact".

2. Great companies are founded & funded in times like this. Funds will continue to search for high quality opportunities to add to their portfolio.

3. Industries with potential tailwinds: gaming, online grocery, productivity, tele-medecine. 

Apr 24, 202010:23
Road Untraveled: Prologis Ventures' Breton Birkhofer on supply/demand shocks, real estate tech, and fundamental changes to the labor force as we knew it.

Road Untraveled: Prologis Ventures' Breton Birkhofer on supply/demand shocks, real estate tech, and fundamental changes to the labor force as we knew it.

Breton Birkhofer, Principle, Prologis Ventures

Key Takeaways:

1. Companies should think critically about the total cost of layoffs, as they also should include the cost of hiring and retraining.

2. The depth and length of the demand shock is still unclear, and it is hard to know just how severe the knock on effects across the supply chain will be for some time.

3. The theory of nice to have vs need to have is being brought to the forefront, and many companies will find out whether or not they are considered critical by their employees as budgets get re-evaluated.

Apr 23, 202019:26
Road Untraveled: RSE Ventures' Matt Higgins on the future of DTC companies, the role of content creation, and playing "offense" in times of uncertainty.

Road Untraveled: RSE Ventures' Matt Higgins on the future of DTC companies, the role of content creation, and playing "offense" in times of uncertainty.

Matt Higgins, CEO @ RSE Ventures / Vice Chairman @ Miami Dolphins

Key Takeaways:

1. Every conversation should start "how can I help you". Investors should think about ways they can relieve their teams of items that have long lead times.

2. The future belongs to the content creators. Build a community and build empathy to your end customer.

3. Teams should look for opportunities to play offense, not just defense.

4. Industries will become more efficient on the other side of this, with tele-medicine adopted much more widely.

Apr 19, 202015:14
Road Untraveled: Ann DeWitt, General Partner of MIT's 'The Engine' on tough tech companies and how this pandemic will bring light to the many global crises we are facing.

Road Untraveled: Ann DeWitt, General Partner of MIT's 'The Engine' on tough tech companies and how this pandemic will bring light to the many global crises we are facing.

Ann DeWitt, General Partner, The Engine

Key Takeaways:

1. This pandemic is highlighting the importance of "tough tech" companies and accelerating their ability to reach milestones and engage customers. 

2. Global issues have been localized as a result of COVID19, and the resulting collaboration of teams working to solve issues like climate change will have a positive long term impact on society.  

3. Founders should continue to think critically about how to operationalize the efforts of their team and ensure continued momentum through these times.

Apr 18, 202012:43
Road Untravaled: Shasta Ventures' Nikhil Basu Trivedi on the importance of employee health, industries to watch and the light at the end of COVID19.

Road Untravaled: Shasta Ventures' Nikhil Basu Trivedi on the importance of employee health, industries to watch and the light at the end of COVID19.

Nikhil Basu Trivedi, Managing Director, Shasta Partners

Key Takeaways:

1. There are a number of behavioral changes that are happening through this environment that will shape the strategy of companies born in the near future.

2. The health of your employee base should be of paramount focus. That includes ensuring that founders monitor themselves.

3. New leaders will be accelerated into leadership positions as a result of this pandemic, and funds will look more diverse as a result.     

Apr 13, 202015:55
Road Untraveled: (UK Edition) GCVs’ Jim Mawson on the global impact of COVID19, the role of debt funding, and what it's like viewing the US response to COVID19 from London.

Road Untraveled: (UK Edition) GCVs’ Jim Mawson on the global impact of COVID19, the role of debt funding, and what it's like viewing the US response to COVID19 from London.

Jim Mawson, Founder and CEO 

Key Takeaways:

1. Corporate VC's can be instrumental in helping their portfolio companies not only have the funding to get through, but a perspective of a customer on how to engage during these times.

2. Debt may become a more compelling financing instrument if equity and VC funding becomes more expensive.

3. In the short term we may see Nationalization and more domestic investing as countries get more protective of the companies being built on their soil. Longer term, value and capital will flow to good companies regardless of where they are built.

Apr 08, 202018:02
Road Untraveled: Shift Ventures’ Jeff Cherry on investing in uncertainty, maintaining culture and how to interact with your investors through COVID19.

Road Untraveled: Shift Ventures’ Jeff Cherry on investing in uncertainty, maintaining culture and how to interact with your investors through COVID19.

Jeff Cherry, CEO, Shift Ventures

Key Takeaways:

1. There is opportunity to invest in short term solutions that get us through the times, but it's also important to focus on "the next big things", and those companies are still being built.

2. Try to get your founders focused on solving the little things- with so much on their plates, paralysis can set in and lead to a lack of execution.

3. Have authentic, transparent conversations with your investors and employees...it will go a long way.


Apr 06, 202017:58
Road Untraveled: Shawn Merani on first-time funds, raising capital and the importance of identifying your champions during COVID19.

Road Untraveled: Shawn Merani on first-time funds, raising capital and the importance of identifying your champions during COVID19.

Shawn Merani, Founder and Managing Partner, Parade Ventures

Key lessons for founders and emerging managers that are preparing to fight COVID19.

Key Takeaways:

1. Bolstering the balance sheet and identifying opportunities to extend runway is one of the most important things a founder can do right now.

2. This process (and pending layoffs) will likely make teams more disciplined, and more aware of where their product is strong and sticky. They likely come out more focused after COVID19.

3. There will be very strong talent available on the market after this, and teams should be on the lookout for engineers and technical talent that otherwise would not be as available.

4. More important than ever to identify your "tribe" and figure out who is in your corner and answering your calls during tough times.

Apr 03, 202019:57
Road Untraveled: Culture Shift Labs’ Andrea Hoffman on resiliency, D+I in the workplace and black leaders setting positive examples during COVID19

Road Untraveled: Culture Shift Labs’ Andrea Hoffman on resiliency, D+I in the workplace and black leaders setting positive examples during COVID19

Andrea Hoffman, Founder and CEO, Culture Shift Labs

Andrea Hoffman and Culture Shifting Labs, among other things, is committed to the success of the Black and Latinx VC community. Through these tough times, she and her partners (including Denmark West) are working to identify the LP's and allies that want to continue and even accelerate this work.

Key Takeaways

1. Founders should be sensitive to the accommodations of the new work day for employees. 

2. Now is the time to be more diverse and inclusive.

3. There is no shame in asking for help during these times. Be specific and ask for "mentorship for today" from those who may have been through prior recessions.

Mar 29, 202018:19