Some investors are motivated by the thought of multiplying their fund, securing a bigger slice of the cap table, or, of course, successfully filing for a coveted IPO. But for Tahira Dosani, all she has to do is remember the economic instability of her childhood and she’s immediately re-anchored to her why behind it all.

First came the career, starting as a Bain Capital consultant and moving on to launching cellular service and mobile payment solutions in Taliban-controlled Afghanistan. Then came the first fund, Accion, a non-for-profit where Tahira cut her teeth in early stage impact investing in emerging markets. 

After Accion, Tahira didn’t set out to start her own fund, but the immigrant-to-entrepreneur pipeline was just too strong and it pulled in this Pakistani native. She co-founded ResilienceVC, a human-centric, early stage fund focused on creating fintech solutions and solving persistent financial challenges for everyday Americans. 

She writes $1 million checks out of ResilienceVC to fintech companies at the seed stage. 

Highlights: 

• Tahira’s why dates back to when she was a child who immigrated to the U.S. from Pakistan. Her family’s financial challenges stuck with her, and ever since, she’s remained focused on helping others boost their economic status through technology. 

• It might be hard to recall a time before cellphone service was ubiquitous, but Tahira was on the ground in Kabul, Afghanistan when the first towers were raised, signalling a new day for citizens’ economic opportunities. She soon after helped launch the first mobile payment solution, bringing even more power to the region. 

• Much of investing in the post-2010s is focused on iterating and refining existing products, but Tahira’s backing OS Benefits, a fintech company with a new answer to an old problem: lack of health insurance coverage for restaurant workers.  

• We often say that AI is changing the game. And now, it’s changing the way we behave. Tahira is exploring how AI can alter people’s financial habits and ultimately, make better choices on their behalf. 

• (00:00) - Resilience as a Thesis- Tahira Dosani on Building for Underserved Markets and AI in Fintech
• (01:21) - Tahira’s path to investing
• (11:52) - How Accion shaped Tahira’s career
• (17:35) - What makes a resilient founder?
• (23:35) - ResilienceVC in the U.S. and beyond
• (28:24) - How Tahira qualifies opportunity markets
• (30:05) - OS Benefits: Solving the under-insurance crisis
• (35:24) - The fintech and AI crossroads
• (43:29) - Common mistakes from fintech founders
• (49:40) - Curiosity as the anchor
• (51:51) - Speed round

We’ve welcomed investors with unique backgrounds to First Funders before, but Sundeep Ahuja is our first operator-turned-actor-turned-investor. 

Sundeep is all in on all things climate tech. He’s backing founders leading the way in cleaning up our water, purifying our air, and keeping our planet the way it should be: livable. Today, his micro fund and syndicate platform Climate Capital, has over 400 climate-focused companies in its portfolio. 

Sundeep shares why he thinks real-world, physical tech has the edge over software, how the words we use matter when it comes to addressing climate challenges, and why he’s still optimistic about the future despite current social and political challenges to climate initiatives. 

He writes ~$150k checks out of Climate Capital into pre-seed and seed-stage startups addressing emission reductions and climate adaptation. 

Highlights:

• Sundeep had a winding path to investing, but his passion for the climate has always been there. He talks about how his time at Kiva shaped and expanded his worldview.
• We’re heard a lot about software, but Sundeep is firmly in the hardware camp. He’s seeing startups like Copper and Avalo make incredible strides working with physical products – or focusing on atoms over bits, as he says. 
• The way we talk about issues matters, and Sundeep is seeing the impact of language play out in the climate space. His solution is simple: No vague, moralizing language. Just plainly state what you’re doing to help the environment. 
• Sundeep has a careful eye on what’s going on regarding the climate and the current administration, but he’s not feeling deterred. He believes there’s still plenty of capital – and plenty of people who believe in the mission – to sustain the headwinds. 
• Like a true investor, Sundeep has a story about his worst investment and what he learned from it. Mainly, that the importance of due diligence can’t be overstated. 

• (00:00) - Atoms over bits: Investing in hardware and innovative founders to solve climate challenges - Sundeep Ahuja, Climate Capital
• (01:39) - Sundeep’s journey from eBay to Acting to Impact
• (02:44) - Finding his purpose at Kiva and focusing on climate
• (03:52) - Establishing Silicon Climate and writing his first book
• (09:17) - Sundeep’s work founding and scaling up Climate Capital to an 400-company portfolio
• (13:45) - Why technical founders and defensible IP are now at the heart of their seed investments.
• (30:34) - Rethinking the language we use to talk about the climate
• (34:58) - Lessons from the worst investment Sundeep has made
• (37:34) - Reasons why Sundeep is hopeful for the future of climate tech

Canadians have been the lifeblood behind some of the biggest unicorn startups of the past few years (think Open AI, Uber, Slack, Instacart, Notion, Databricks, CloudFlare, Roblox, Ethereum, Moderna Health, and Clay to name a few), and yet no one talks about them, except for Andre Charoo. And he’s not just talking – he’s putting his money behind Canadian founders through his fund, Maple VC. 

Andre shares why he thinks Canadian founders are always a strong bet (and bonus points if they’re immigrants, too), what it’s like to wait over 7 years to see a pre-seed investment materialize (in this case, recent unicorn Clay), and how he thinks about moats in the AI age (and why they still matter).

Maple VC writes $500k – $1.5 million industry-agnostic checks into pre-seed and seed stage companies with roots from Canada to Korea to Harvard. 

Highlights

• Even long after he left Uber and Hired, Andre never lost his go-to-market spirit and he’s carried it with him as he’s moved from operator to VC. 
• Andre’s investing framework can best be described as Canadian roots with global reach. He’s been working hard to give Canadian founders their due and show their world that they are some of the most ambitious people out there. 
• Clay, a unicorn in the Maple VC portfolio, is a testament to persistence and patience. Andre urges investors to remember they’re playing the long game – waiting for results that may not materialize for nearly a decade. 
• It’s all about building durable companies, and the 7 Powers by Hamilton Helmer still holds true. Andre stresses that defensibility and success come from strategic insight, execution, and taste—not just code.
• While AI is changing the way companies form and scale, Andre still believes in this undefeated combo for founders: inventors, builders, and operators.

• (00:00) - Andre Charoo, Maple VC - Before Clay Was a Unicorn: The First Check, the Thesis, and the Long Game
• (01:40) - Andre’s journey from operator to investor
• (06:56) - Why Andre will always bet on Candian expats
• (22:46) - Andre’s check size and how he manages Maple VC
• (33:38) - The 7-year story of the unicorn, Clay
• (42:14) - Where Andre thinks AI stands and where it might be going
• (49:17) - Moats still matter in the AI era
• (01:03:02) - Andre's take on the inventor-builder-operator trifecta

You can be a founder. You can be an investor. You can be an operator. Or, you can be Shalin Mantri and be all three. This respected product leader got his start by founding a mobile app startup in the early iPhone days in 2011 and followed it up with product leadership in the early days of Uber, Skip and more recently, Google. He angel invests with $5k – $50k checks as a true first believer, usually in companies where he has a personal connection with the founder. 

He shares his tiered angel investment system, where he sees autonomous vehicles going (and not going), his thoughts on AI, how AI might have transformed Uber’s early days, and what he thinks of the rise of multi-billion-dollar, 1-pizza companies. 

Highlights

• Shalin has a tiered system for evaluating angel deals, and ultimately, determining how much he’s willing to invest.

• Uber experienced incredible growth from its founding in 2009 through the 2010s when Shalin came aboard as a product manager. He chats about how he thinks AI would’ve changed Uber’s story if it had been around at the time. 

• Shalin explains how AI is running a parallel path with autonomous vehicles, especially when it comes to scaling up without losing product integrity. Just like with AVs, the bar is high for reliability, safety, and performance for AI tech. 

• Recently, the search bar has been less of a source of information and more of a source of frustration. Shalin is focusing on building a solution to improve search, with the help of AI, of course. 

• Company headcounts are getting smaller, and yet their valuations are getting bigger. Shalin’s not necessarily sold on the 1-company, 1-billion dollar company just yet, but he sees the trendline moving in that direction. 

• (00:00) - 01 - Shalin/Shaherose A/V
• (02:19) - How Shalin evaluates angel deals and deploys checks
• (13:20) - Working at Uber during the early(ish) days
• (17:59) - Not all growth is good growth
• (26:26) - Exploring the interplay between AI and AVs
• (34:07) - When the big bet doesn’t lead to the big payoff
• (37:42) - Why AI is making it a confusing and exciting time for PMs
• (42:51) - What’s wrong with search these days? Is search being rewritten - again?
• (46:40) - Scaling companies down to 1 pizza and 1 pizza only
• (58:39) - Shalin’s AI angel investments

We’ve had a lot of cool people on the pod, but Sheel Mohnot is our first guest to achieve this trifecta: 100X an investment, have a founder in his portfolio go to prison, and have his wedding sponsored by Taco Bell. He invests at the pre-seed and seed stages into startups in the financial technology (fintech) space, and he’s quick to tell you that just about everything is fintech. Through his fund, Better Tomorrow Ventures, Sheel writes $500k to $3M pre-seed and seed checks into fintech companies. He came by to talk about that time he got defrauded by a company, how he sparked a bidding war that led to him returning most of his fund, and why speed of execution is one of his favorite traits in founders. 

Highlights:

• Sheel is beginning to think that pre-seed is the new seed, and seed is the new Series A. He unpacks these thoughts and outlines what he needs to see in order to believe in a founder at the early stages.
• Secondaries and early exits and two ways investors can realize an outcome in a shorter time frame than an IPO. Sheel explains how he did this with two companies, Flexport and Indio, and how he feels about his decisions retrospectively. 
• Major companies like Toast and Shopify are synonymous with fintech, but there is a vast network of less-thought-of companies making transactions happen in nearly every imaginable space. Hair salons, golf clubs, and garbage trucks are just a few of the places where Sheel is seeing fintech potential and why he believes that everything is fintech and fintech is everything.
• Sheel could’ve saved himself some trouble (and money!) if he would’ve heeded the warnings of fellow investors about a deal. However, he learned his lesson and now he doesn’t invest unless he thoroughly vets the founder through someone else in his network.

• (00:00) - FIFU 16 - Sheel Mohnot
• (01:25) - Sheel's early days as a founder and consultant
• (09:58) - Why invest and why invest in fintech
• (12:09) - Ideal Founder Profile: Who and what Sheel is looking for
• (14:43) - Lessons From the Worst Investment: How to spot a fraud
• (21:10) - Lessons from the Best Investment: Knowing when to take chips off the table
• (34:03) - Sheel's thoughts on the expansiveness of the fintech market
• (38:00) - Speed of execution is one of Sheel's favorite traits to find in founders
• (43:31) - Speed round

One day soon when you see a robot squirrel on a 10-foot unicycle, think of Danielle Strachman. These are the types of ideas Danielle Strachman sees and backs on a regular basis at her VC fund, 1517. 

The fund, which proudly backs “dropouts, students, and sci-fi,” has had several fund multipliers in their portfolio, including Loom (Acquired by Atlassian) and Luminar Technologies (IPO 2020). Plus, her star-studded community includes Vitalik Buterin of Ethereum, Laura Deming of The Longevity Fund, and Dylan Field of Figma – all of whom she first met when they were teenagers. 

Danielle’s commitment to bringing freedom and autonomy to young people is much of the reason behind 1517’s work with upcoming founders — which includes children as young as 10 years old! 

We talk to Danielle about why her firm hands out cash grants to kids, where she sees the future of deep tech headed and how she’s helping it get there, the right characteristics (and anti-characteristics) to look for in founders. 

Danielle invests $100k angel checks and $500k pre-seed checks out 1517 Fund focusing on dropouts and sci-fi / deep tech founders.

Highlights:

• 1517 exists to address the lack of capital for young people and for the deep-tech sci-fi space. Danielle is particularly drawn to “dropouts” who skipped the higher education path to focus on their work and start their companies. 

• Danielle likes to think of her fund as Grand Central Station, a place that helps people get to where they want to go next. She uses her relationship building skills to stay in touch with founders and connect them with new opportunities.  

• Danielle loves meeting “crazy scientists” and people who are working on solving the future’s problems. 1517 is unique because it makes two investments in these types of companies: a $100k angel check for R&D and a $500k pre-seed follow-on check. 

• Danielle understands the power or relationships and mentorship in a space that can often feel impersonal and transactional. She’s kept in touch with many founders over the years, including the founders of Loom and Luminar Technologies – whom she met back when they were teenagers! 

• (00:00) - FIFU 15 - Danielle Strachman
• (06:41) - The 1517 Differentiator: An anti-establishment fund for dropouts
• (08:15) - The Why: Bringing freedom and autonomy to young people
• (18:49) - 1517 as Grand Central Station: Helping people get to their next destination
• (26:35) - Lessons from the Worst Investment: Listen to your gut
• (35:24) - Best Investments So Far: Loom and Luminar Technologies
• (37:54) - The Fund Formula: 85% dropout and 15% sci-fi
• (51:47) - Nurturing Young Talent: How Danielle sources next gen founders
• (57:34) - Speed round

Elizabeth Yin realized she had a problem. She wanted to be a founder, but couldn’t think of a problem she wanted to spend decades of her life working on. After soul searching, she remembered the one thing she did care about: helping other founders.

She took that passion and turned it into Hustle Fund, which focuses on offering capital, knowledge, and networks to “hilariously early-stage” software startups. She also angels invests in non-software D2C companies. She’s invested in over 800 startups, with two of her most notable being Webflow and Mejuri. 

We chat with Elizabeth about why valuation matters if you have a smaller fund, why she thinks certain hot spaces like AI might not yield the types of returns investors think they will, and what happens when founders misbehave (and commit fraud and flee to Russia). 

Elizabeth invests $150k checks into idea-stage B2B software, digital health, and fintech companies through Hustle Fund. 

Highlights: 

• When Elizabeth says she invests at an early stage, she means it. Hustle Fund invests in founders who have an idea and are pre-revenue.

• Elizabeth talks about the difference between small sub-$100M funds and large multi-stage funds. As a smaller fund, you need to make your checks count by deploying them into startups where they’ll make a true difference. Multi-stage funds are investing early to have the option to write a bigger check in later stages. 

• Higher exits usually mean higher entry points for investors. If you’re not a multi-billion dollar fund, you probably want to focus on investments with lower entry points and in return, lower multiples. In the end, both lead to similar quantified outcomes.

• You don’t want to invest in overcrowded spaces because your chances of realizing alpha decreases when there are more hands in the pot. Finding unpopular spaces with less competition is where Elizabeth likes to focus.

• (00:00) - 13: Elizabeth Yin of Hustle Fund has seen over 50,000 companies and made 800 investments – usually in just 30 minutes
• (01:36) - Launching LaunchBit: Getting started as a founder and helping others at the same time
• (09:30) - The first investment: Lessons in customer acquisition
• (11:48) - Valuation: Why it matters at every fund size
• (18:43) - Making checks count: Are you an option or an investment?
• (28:37) - The best investment: Lessons in learning to play the long game
• (30:59) - Entries and exits: Elizabeth's framework for evaluating investments
• (39:39) - Ignoring the crowd: Staying out of too-hot spaces like AI
• (49:52) - AI: What’s Elizabeth doing in this space?
• (53:23) - Speed round

An ill-fated business school fashion show led to a venture capital fund with $215 million AUM. 

The duo met in 2010 at the MIT Sloan School of Management and soon after became research partners investigating why VCs were shunning startups in highly regulated spaces even though AirBnB and Uber were starting to reach venture scale very quickly. Tech-enabled startups impacting how we live in the real world were new (back then). Their research sparked Tumml in 2012, an early-stage accelerator, and culminated with the Urban Innovation Fund I in 2016. Now on their third fund with $215M in AUM and multiple exits, including CodeSpark Academy (acquired by BEGiN) and Electriphi (acquired by Ford). 

In this episode, Clara and Julie share how they lean into regulated spaces, take advantage of macro trends, and uniquely focus on the relationship between cofounders when investing—lessons from their own highly effective partnership.

Clara and Julie invest $500K to $3M into pre-seed and seed startups that make cities more livable, sustainable, and economically viable. This urban thesis covers sectors like climate tech, financial services, transportation, fintech, education, proptech, and future of work.

Highlights: 

• Clara and Julie had a hypothesis that urban tech was not only going to take off, but that it was also worthy of VC capital, contrary to what some of the top VCs thought at the time. 

• Sometimes, the role of an investor is to support other investors just as much as the founders. Clara and Julie explain the importance of being the investor who steps up and gains consensus among the other LPs when disputes or dilemmas arise. 

• The opportunity to invest in Electriphi, an electric vehicle fleet management software company, led to an acquisition that returned most of their second fund – all because they were brave enough to bet on the macro trends and tailwinds. 

• Matching up founders with opposite skill sets might work out, but Clara and Julie would much rather find people who truly mesh on deeper levels. 

• (00:00) - FIFU 13 - Julie Lein & Clara Brenner
• (03:22) - A new kind of VC: The Urban Innovation Fund
• (11:16) - Opposites attract? Optimizing for cofounder-cofounde fit
• (18:42) - What are Julie and Clara’s whys?
• (23:43) - Lessons from the first check: They won’t all be unicorns
• (33:23) - Lessons from the worst investment: The only failure is giving up
• (39:01) - The bear hug: Avoiding the bystander effect and getting other investors on board
• (44:37) - Lessons from the best investment: Catching Electriphi and the regulatory tailwinds
• (49:26) - Sensing change: The power of investing in a not-hot space
• (51:08) - What’s next: Looking ahead to the next 5 years of investing
• (58:03) - Becoming a better investor: What’s the secret?
• (01:04:20) - Pattern matching: What it is and what it isn’t to Julie and Clara
• (01:10:51) - Speed round

Have you ever played with an Oculus VR headset? You probably owe thanks to Arian Ghashghai. The former founder was working at Meta when someone in his network introduced him to an opportunity to invest in gummies. Yes, gummies. 

That’s far and away from Arian’s machine learning roots, it’s now one of his best investments to date. Arian has since gone full-time into investing as the founder and managing partner at his own fund, Earthling VC, which specializes exclusively in making pre-seed investments into companies in the AR/VR and robotics domain. One of his investments is on track to do $20M in revenue this year after only needing to raise a single $1M round. We cover a lot of good ground in this episode, and we really get into how the rise of these “raise-once” companies is changing traditional VC models. 

Arian invests $25K to $200K in pre-seed AR/VR and robotics startups through Earthling VC. 

Highlights: 

• Arian was a founder and quickly realized he hated being a founder. He started at Meta as an applied machine learning software engineer and angel invested for the first time in a CPG company, a decision largely driven by how impressed he was by the founder. 
• To Arian, worse than losing money is being labeled as another dime-a-dozen investor with no unique insight or edge. That’s why he advocates for being a big fish in a small pond to reduce competition and make it easier to stand out. 
• Arian explores why VCs have traditionally been skittish about getting into VR and robotics, and why there’s never been a better time than now to start investing in these categories.
• Arian is seeing a trend among companies that only need to raise capital once before they can rely on their own profitability. 

• (00:00) - How one of Arian Ghashghai’s virtual reality companies is on track to hit $20M in revenue after one round of funding
• (00:29) - Welcome, Dan Hightower, a new co-host!
• (02:00) - How Arian got into investing: Meta, friends, and gummies
• (09:13) - Invest in the top 1% of founders
• (13:02) - Treat your angel investing fund as a portfolio
• (16:40) - Marker
• (21:05) - On realizing deep tech was going to change everything
• (27:20) - The four measures of an extraordinary founder
• (31:46) - Lessons from the worst investment: Don't fall in love with your expertise
• (36:01) - Check size, scaling, and sourcing
• (44:12) - Truffle hunters vs. heat seekers
• (47:19) - Speed round
• (59:44) - Bonus Qs: The rise of raise-once companies and why aren’t investors investing in robotics and VR content?

Armed with an educational background in computer science and biomedical informatics, Amit Garg switched to venture capital after a long, successful career in the corporate world, which included stints at companies like Google and Samsung.

And that’s just the way he never planned it. 

That’s right, the almost-doctor didn’t intend to get into venture capital, and he certainly never planned on starting his own fund. He was drawn in by his innate need to build things, including relationships with people. He partnered up with his officemate from Norwest, Sanjay Rao, and the two started Tau Ventures in 2019, an AI-first, early-stage fund focused on healthcare, enterprise, and automation. 

Amit tells us about his very targeted approach to investing, which is different from the “spray and pray” method we’ve seen from friends of the pod and other investors in general. We also get to hear first-hand accounts about the importance of building trust with your investing partners and your founders. Plus, Amit gives us his take on the state of healthcare and AI and why – despite all the challenges – he’s hopeful about where it’s headed. 

Amit primarily invests $500K in Seed-stage healthcare, enterprise, and automation startups and occasionally in Series A, B, and C through Tau Ventures. 

Highlights:

• Amit turned down a spot in medical school and pivoted his original ambition to become a doctor by first joining Google, pivoting to VC, and then becoming a digital health founder.
• He got into the corporate side of venture capital after business school, but he never had any interest in starting his own fund. That is until his friend and former officemate convinced him that an AI-first venture fund was a great idea in 2019. 
• Amit explains that the “why” behind his investing does come from a place of self-interest – which is much different than selfish. He feels that when he pursues and realizes his own self-interests, he can help others to the same.
• Why a founder shut down a company in his portfolio and why Amit decided to back him again basically the next day. 
• How he sees the interplay between angel and institutional investors and why they’re both necessary 
• Amit’s frustration with healthcare and how it fuels his passion to make it better. Plus, he explains why he keeps his focus on the three legs of the healthcare tripod.  

• (00:00) - FIFU 11 - Amit
• (02:30) - Amit’s journey into venture
• (06:08) - Why Amit likes venture capital as someone who wants to make the world better
• (13:01) - Memorable moments from the first conviction-driven investment: Iterative Health
• (19:18) - The machine gun vs. the shotgun style of investing
• (21:05) - Lessons from the worst investment
• (24:34) - Be careful who you partner with, optimize for good investors
• (28:22) - What the best investment with a $450M exit taught Amit
• (32:57) - Investing is about humans believing in humans
• (35:42) - The state of healthcare and AI today
• (46:39) - Venture vs. angels in the healthcare space
• (51:12) - Outcomes in the digital healthcare space are starting to behave like tradtional SAAS software outcomes
• (58:13) - Lighting round
• (01:01:51) - Takeaways

What do you get when you mix U.S. national security, angel investing, and kids’ pajamas? Atlee Clark. Proud Canadian Atlee took a hard pivot from the public sector to the tech world, first through a nonprofit called the C100, which supports entrepreneurs, and later at Shopify, focusing on 0 - 1 initiatives. Similar to other angel collectives emerging at the time like Hashtag Angels and Operator Collective, Atlee tapped into her executive network at Shopify to connect with other female leaders who were looking to invest on the side. 

What began as informal conversations about investing and advising after the working day coalesced into Backbone Angels, a collection of executive tech women sourcing angel opportunities collectively and making investments individually. Backbone was started in 2021 and has amassed a portfolio of over 40 early-stage startups, including Bird&Be, 1Password, and Blume.

Atlee tells us what it’s like to balance functioning as a cohesive unit while making individual investment decisions. Plus, we get to hear about her journey as a small business owner and what motivates her to invest in what she wants to see in the world. 

Atlee writes angel checks of $10k to $20k, ideally at the friends and family round or at pre-seed, focusing on startups that address challenges for parents, small business owners, and Big Tech execs—three areas she intimately understands as the end user. Backbone Angels focuses on companies led by Black, Indigenous, and Women-led startups. 

Highlights:

• Atlee hopped on a one-way plane to San Francisco and left her U.S. national security gig in Washington, D.C., behind to head up a nonprofit organization supporting Bay Area Canadian tech entrepreneurs (and she’d never even worked in tech!)
• She met early Shopify execs who convinced her to come work for the company doing developer relations and the app ecosystem. Casual conversations about investing and advising with her peers led to the creation of Backbone Angels.
• Atlee prefers to follow her own intuition with early-stage investing, but she does have a tried-and-true framework for determining if a deal is right for her. She shares her tips for working as a collective and the reason she believes you should never overthink a “no.”
• Angel investing is a side hustle for Atlee (Remember, she’s also a Shopify exec, small business owner, and mom), and she prefers it because it fulfills her in a way that going full-time wouldn’t.   

Resource:
Want to Angel invest with other operators and learn from the team at Hustle Fund? Check out Angel Squad and resources created by Brian Nichols

• (00:00) - Atlee Clark, Angel: Canadians breaking into tech and now investing with intuition and purpose
• (01:33) - Building an ecosystem for Canadian tech founders: the story of becoming the first CEO of the C100
• (06:38) - Meeting Tobi Luke and joining Shopify: a new adventure pre IPO
• (09:34) - Founding Backbone Angels: a collective of senior leaders at Shopify coming together to write checks
• (15:27) - First Investment: The power of patience and a developing a personal investment thesis
• (23:21) - Worst Investment: Trust your gut and staying patient
• (29:20) - The art of feeling a "no"
• (30:54) - Best Investment: Highlighting Top Performers Calico and MIrza
• (32:59) - Resilience in Founders: Overcoming Challenges
• (34:15) - Current Investment Strategy: Today's Focus
• (38:21) - Sourcing Deals: Networking and Connections
• (44:46) - Lightning Round ⚡

Join Shaherose & Aamir as we reflect on our conversation with Charles Hudson of Precursor Ventures. 

Highlights: 

• Don’t forget the macro: Government regulations can lead to massive opportunities or failures. We discuss case studies of companies like Samsara, Movtive (fka KeepTrucking), Republic, and Zum, showing how regulatory shifts led to category-creating opportunities. Charles’ worst investment was wiped out due to changes in government regulation. 
• Team vs market: We discussed the interplay between having the right team, idea, and timing for startup success. Charles evaluates opportunities 70% team and 30% idea. Both Aamir and I take a more balanced approach than Charles does.
• Fund size vs. outcomes: Reflecting on the past learning, "Your fund size is your strategy." We wonder what role that played in Charles’ decision to invest in the Athletic, later acquired by the NY Times for $550M.

Links:

• Follow Charles Hudson on Twitter: @chudson
• Read Charles’ blog on Substack
• Learn more about Precursor Ventures: Precursor Ventures
• Connect with Charles Hudson on LinkedIn: Charles Hudson

Connect with Us:

• Follow the First Funders Podcast
• Newsletter with behind-the-scenes access and key takeaways
• Twitter/X: @shaherose | @avirani
• Email us with feedback and suggestions on topics and guests

Disclaimer: This is for information purposes only. This is not investment advice.

• (00:00) - Introduction and Format Change
• (00:39) - The macro matters
• (03:40) - Learning from past investments while staying open minded, what about bias?
• (04:12) - Team vs. Market
• (10:36) - Fund size vs outcomes
• (16:17) - Investors don't know it all

Hailing from Michigan, Charles developed an early obsession with the public markets in high school. Charles Hudson is now the Managing Partner at Precursor Ventures, a pre-seed venture fund that has defined and has become synonymous with “pre-seed”. Charles is known for his ability to identify and mentor early-stage companies that have the potential to disrupt their industries - first and early - including companies like the Athletic (acquired by the NY Times for $550M), Bobbie (recently raised a $70M Series C), Carrot Fertility (recently raised $75M Series C) and Pair Eyewear (recently raised $75M Series C).

Charles writes checks of $250k - $500k at Pre-seed and Seed. He is a Generalist with a focus on digital health, media, and software.

Highlights:

• The boomerang back to VC: Charles shares his unique path from Michigan to Silicon Valley, starting in VC, then moving to Google and various startups before returning to VC.
• Founding Precursor Ventures: Charles spotted an opportunity to invest in non-obvious founders pre-product and pre-revenue while other firms moved upstream in 2015. This made him one of the first in a second wave of pre-seed firms to launch, and 10 years later, he’s become the go-to first funder.
• Evaluating Founders vs. Ideas: Charles is a founder-first investor (founder 70%, idea 30%). He shares his criteria for assessing talent and reveals indicators of success that have generated alpha in his portfolio.
• Investment Strategy over Trends: Even in the face of trends like crypto, AI, and the economic downturn, Charles stays steady and focused on people and his definition of pre-seed, not morphing with industry shifts.

Links:
Follow Charles Hudson on Twitter: @chudson
Read Charles’ blog on Substack
Learn more about Precursor Ventures: Precursor Ventures
Connect with Charles Hudson on LinkedIn: Charles Hudson

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Disclaimer: This is for information purposes only. This is not investment advice.

• (00:00) - Intro
• (00:52) - Early Days and Building Community
• (03:09) - Interning at Smith Barney to the CIA's Venture firm
• (08:59) - Embracing Risk and Independent Thinking defines a solo GP
• (11:05) - Operating Experience As Product Manager, then Business Development at Google and a Return to VC
• (16:50) - Charles' first role as an advisor surprisingly had a $300M acquisition by Paypal
• (19:55) - Joining Softech (now Uncorked) in 2010 when Seed investors were known as Super Angels
• (21:10) - Launching Precursor to fill the gap created by Super Angel Funds going upstream and defining a new category - "pre-seed"
• (23:50) - First Investments: the role of macro tailwinds and headwinds
• (27:57) - Evaluating Founders 70% and Ideas 30%
• (31:03) - The Role of Business Model Innovation in Generating Alpha
• (33:25) - Learning from Challenging Investments: If you don't know its ok, but say something
• (38:01) - Staying True to Your Investment Strategy
• (40:44) - Charles' best investment: The Athletic, acquired by the New York Times for $525M
• (45:55) - How he Decides: Evaluating Founders and Their Potential, Weird Patterns, Product Velocity, Remote Teams
• (51:38) - Current Investment Strategies, Focus Areas and Check Sizes
• (53:25) - Following High-Potential Talent vs. Investing Theses: People vs. Market vs. Product Evaluations
• (57:00) - Speed Round

Eric Ries has invested in over 100+ early-stage startups. He is best known as the author of The Lean Startup, a must-read for entrepreneurs worldwide. He also founded the Long-Term Stock Exchange (LTSE), a new stock exchange designed to support companies with long-term goals. He recently launched a new podcast discussing ways to re-think corporate governance to be mission-first.

In Part 1 of our interview, he shared insights from angel investing. In Part 2, Eric shares his new ethos for startups rooted in long-term thinking, putting a company’s mission at the center of everything and aligning all stakeholders. This mission-first approach challenges the traditional capitalist, and data shows it leads to better company performance.

Eric writes checks of $10K or less as an Angel at the earliest stages. He is interested in mission-driven founders, education, fintech, AI, and more.

Highlights:

1. Eric Angel invests for reasons beyond financial outcomes. He focuses on giving back to people in his network, learning about startup approaches and various industries, and doubling down in areas he is passionate about. Any time he has strayed from his investing criteria, it hasn’t worked out. 
2. Advising then investing: Eric prefers to work with a startup as a friend or advisor before investing. He keeps his check size to $10K to support his goal of high-velocity learning. He can write more checks with smaller checks, which means more learning.
3. Investing as a spiritual journey: Eric practices introspection to support continuous learning and to avoid overgeneralizing when things don’t work out. When he invests, he applies Lean Startup thinking by asking, “Is this outcome falsifiable”? Invest -> Measure -> Learn. We guess this makes him is a "Lean Investor"
4. Eric’s second act after Lean Startup is supporting mission-first startups: He advocates for a new ethos that he believes will lead to better performance in the long term.
5. Eric shares tools for mission-first founders, including the Public Benefit Corporation, the LTSPV, employee voting trust, and more.

• (00:00) - Introduction to First Funders
• (00:54) - Meeting Eric Ries: a journey down memory lane
• (02:45) - The Impact of Lean Startup
• (07:15) - Eric's Angel investing journey starts with being an advisor and a mindset of giving back
• (09:55) - What is Eric's investing criteria
• (14:04) - Eric prefers to advise startups first before investing
• (17:47) - Eric's second act: from Lean Startup to nurturing mission-driven founders who will also realize massive profits
• (25:14) - Writing small $10K checks into a high volume of early-stage startups enables high velocity learning
• (27:24) -
• (28:28) - Eric decouples investing from outcomes to stay focused on giving back and learning
• (30:44) - How to be a useful startup advisor: stand for something that creates competitive advantage for startups
• (34:31) - A challenging investment: lessons from high-stakes and high-stress moments and can the startup journey be a force for healing trauma?
• (43:04) - The Long-Term Stock Exchange vision: a new ethos and governance approach for the startup community
• (45:01) - How mission-driven founders and investors need to be brave to challenge the capitalist status quo
• (47:33) - How tech startup can leverage the Public Benefit Corp and how the B-Corp certification won't work for software companies
• (51:24) - LTSPV: An SPV Angels can leverage to align their check with long-term thinking
• (54:08) - The spiritual journey of investing: what did you really learn vs what do you think happened?
• (57:07) - Speed Round and Final Thoughts
• (59:24) - Takeaways

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Disclaimer: This is for information purposes only. This is not investment advice.

Rajiv Bala, GP of Clutch VC, a pre-seed and seed-stage fund exclusively investing in Texas. Rajiv is committed and bullish on the region with a hands-on approach to investing, working with founders on product feedback, team building, and more to see initial customer validation before investing. Rajiv also embraces sub $500 million outcomes to drive fund multiples rather than relying on Unicorn outcomes only. This episode pushed our thinking on what we know and practice here in Silicon Valley, reminding us that there is more than one way to achieve Alpha.

Highlights from our discussion:

• Starting startups, Texas style: Is it about 24/7 work-life or work-life balance? We discussed a Texas vs. Silicon Valley approach to company building. Can it work and drive outsized venture outcomes?
• Beyond chasing unicorns: Can you be successful with sub $500M outcomes in VC? We dug into how portfolio construction starts with fund size and what scale of outcomes matters to you.
• Does previous founder or operator experience make you a better investor? Rajiv believes it builds founder empathy, skills, and experiences that make you more effective in challenging moments.
• Selective incubation as a strategy: Rajiv will sometimes work with a team for 6 to 12 months before investing to gain information asymmetry, build conviction (or incertitude), and establish a genuine relationship ahead of the check. 

Topics

• (00:00) - Introduction to First Funders
• (00:58) - Meet Rajiv Bala: GP, Clutch VC
• (01:34) - Rajiv's Journey into Venture Capital
• (03:27) - The Texas Startup Ecosystem
• (07:44) - Texas-style company building: work-life balance and outcomes
• (11:06) - Rajiv's lessons on portfolio construction: diversification and fund size as key levers
• (14:08) - Where and how Rajiv sources deals in Texas
• (17:16) - Rajiv's "why" for investing: led to his hands-on investing approach
• (21:01) - Lessons from Early Investment Furnace Software: an early DevOps leader bought by BMC
• (30:03) - Rajiv's lessons from his worst investment came with an opportunity to build founder empathy on how hard the journey is
• (35:38) - Rajiv's best investment: he Converse AI journey
• (40:21) - A higher valuation isn't the end game, pick your investors for a long game
• (42:10) - Selective incubation: Rajiv builds relationships with Founders before the check and wants to see the product reach initial traction
• (48:48) - Clutch's Investment Strategy and Market Focus
• (59:13) - Key Takeaways and Final Thoughts

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Meka Asonye, a Partner at First Round Capital, started angel investing in 2018 while working at Stripe and joined First Round in 2021. He has made dozens of Angel investments and 13 Venture investments, and he's just getting started! While he focuses on B2B SAAS, he has not shied away from investing in audacious founders, from modernizing 911 call centers to putting the biggest satellites in space. Meka shares his approach to finding true outliers, a practice he began while uncovering hidden talent for the Cleveland Guardians. 

Meka writes checks of $2M to $5M as the lead at pre-seed and seed.

Highlights from the discussion:

• Meka's unconventional path to VC: from discovering high-potential baseball talent to leading sales at startups to VC
• Meka's first angel investment came from Craiglist!
• Exploring the frontiers: investing in Space and GovTech
• How Meka supports founder friends, honestly
• Leveling up in VC by learning from partners, retros, reviews, and reflection powered by process and data

This is for information purposes only. This is not investment advice.

Topics

• (00:00) - Kicking Off the First Funders Podcast with Meka Asonye
• (03:52) - First Round Capital's role in Meka and Shaherose's transition from Angel to VC
• (05:53) - Meka's Unconventional Path to Venture Capital: from baseball talent to management consulting to startups to VC
• (10:54) - Meka's purpose is rooted in being a part of the founder's village
• (13:55) - The Art of Angel Investing: Meka's First Investment Story came from a person he met on Craiglist!
• (18:37) - Thoughtful reflection: outliers can't be discovered via pattern matching
• (20:15) - How Meka assesses for money smells and hustle in a founder
• (23:16) - Missed deals like Anthropic keep Meka up at night.
• (28:10) - How Meka supports founder friends
• (33:42) - Outcomes and up rounds thus far: Rimeto, CODA, K2Space, Prepared
• (36:16) - Exploring the Frontiers: Investing in Space and GovTech
• (37:42) - Meka's betting on a pair of brother's putting big satellites in space
• (39:04) - Unexpected VC bet: Integrating tech into every 911 emergency call
• (43:31) - Meka is a generalist investor with a focus on B2B SAAS, Fintech and hard tech
• (44:54) - Investing in YC companies and maintaining an orientation towards prioritizing ownership over valuation
• (49:28) - First Round Capital's approach is rooted in consensus not conviction, they invest as team
• (52:17) - Leveling up in VC by learning from partners, retros, reviews, reflection powered by a process and data
• (01:07:47) - Outro

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Amit Kumar, former founder and angel investor, is a generalist venture capitalist at Accel focused on dev tools, healthcare, and fintech startups. Twitter acquired Amit’s third company, and it was then that he realized his true purpose was supporting startup founders, and he shifted to venture capital. Amit shares insightful stories and lessons learned from 8 years of early-stage investing out of a large, top-tier VC fund.

Amit writes checks of $2M to $4M as the lead and first institutional seed investor. 

Highlights from our discussion:

• How Amit frames venture capital as a long game
• Why Amit considers himself a “co-founder as a service,” and how that serves his startup community
• The right way to think about deal setup for successful early-stage investing
• Why the problem slide in your pitch deck is most important

This is for information purposes only. This is not investment advice.

Topics

• (00:00) - 04: Amit Kumar - Accel
• (00:16) - A startup idea seed investors will definitely say NO to (but maybe Shark Tank will take it)
• (03:35) - Amit Kumar - seed investor and First Funder at Accel
• (05:17) - Amit's Transition to Accel and the Power of Networking
• (07:38) - How Amit learned about angel investing - friends, conferences, and meetups
• (08:47) - What does it look like when a VC firm recruits you as a potential founder? Potential partner?
• (12:14) - Angel investing as risk diversification and knowledge sharing, especially for existing startup founders
• (13:56) - Venture capitalists can provide "co-founders as a service"
• (17:21) - How Amit chose between being a founder again and investing full-time
• (20:06) - Amit's first investment, and how past founder relationships build trust
• (22:23) - Startups that don't go public in 7 years - does that hurt your model and LP relationships?
• (24:11) - Conviction, not consensus - but what builds trust among GPs when startup investing?
• (26:30) - Startup valuations: Amit's venture capital POV and moving targets in 2024
• (28:37) - How does a large early-stage VC think about follow-on investments and the number of startups to fund?
• (31:57) - Taking bigger risks earlier
• (34:49) - How startup investors consider incumbents in a space when assessing competition and exits
• (36:24) - Headway, and what Amit has learned about identifying good startup investments in new markets
• (42:05) - How to think about thesis investing, conflicts of interest, and competing startups
• (45:14) - How Amit thinks about return profiles and seed investing today
• (48:08) - What founder and market signals does a venture capitalist look for?
• (50:39) - How to get on the Midas List - it's the fundamentals
• (51:47) - A movie you must see to understand venture capital and startup investing matters
• (54:15) - Takeaways from Amit Kumar's First Funder approach
• (01:01:18) - Outro

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Rachel Sheinbein is an angel investor with over 250 startup investments.  She shares her insights on angel investing and how it allows her to work with founders “even before the seed stage,” writing $25k checks into technology startups through her vehicle Very Serious Ventures.  Later, Rachel discusses how building a community drives her investing strategy and lessons from memorable startup investments.  Shaherose and Aamir kick off the show with a special message for founders who like to argue and end with their personal takeaways from the conversation with Rachel.

Highlights from our discussion:

• Why Rachel chose angel investing over a partner position at a VC firm
• What to look for in a quality angel group
• Using a DAF to align with an investing purpose
• Detecting founder passion and coachability
• Defining your purpose

This is for information purposes only. This is not investment advice.

Topics

• (00:00) - 03: Rachel Sheinbein, Angel
• (01:14) - PSA: Your startup's users know more than Aamir the angel investor does
• (02:51) - Rachel Sheinbein, angel investor and advisor
• (04:56) - From engineering to venture capital to angel investing
• (07:28) - Do angel groups and angel networks provide value to startup investors?
• (13:23) - How Rachel aligns purpose and philanthropy with her early-stage startup investing
• (16:08) - Rachel's first angel investment was in a gaming startup
• (19:17) - Investor experience, startup luck, and Sequoia
• (21:49) - How does an angel investor like Rachel measure bad outcomes in startup investments?
• (24:53) - How angel investors operate differs from venture capitalists
• (29:47) - Pitch decks - do they matter when seed investing so early?
• (33:45) - Startup founder signals that matter to an angel investor
• (40:47) - A climate tech seed investment that paid off quickly and returned funds
• (46:39) - Very Serious Ventures angel invests $25k super early in founders
• (48:51) - An exercise to help you become a better angel investor
• (51:04) - Speed round, and the best book on strategy for startup founders
• (52:59) - Our takeaways on better startup investing

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Jenny Fielding, a pre-seed investor and angel with 300 early-stage startup investments, discusses investing in FinTech, hard tech, and consumer spaces over the past decade. From studying law to working in finance to leaving it all to found not just one but two startups, Jenny brings a founder-operator mindset to her fund, Everywhere Ventures. She writes pre-seed and seed-stage checks for $50k to $250k.

Highlights from our discussion:

• Jenny’s first seed investment and its fast, huge outcome
• Her simple evaluation framework for startup companies and their founders
• The way larger funds can screw early angel investors
• Everywhere Ventures’ latest seed investment comes out of stealth
• A yearly ritual to become a better angel and startup investor 

This is for information purposes only. This is not investment advice.

Topics

• (00:00) - 02: Jenny Fielding - Everywhere Ventures
• (03:07) - How does Shaherose know Jenny?
• (04:17) - Jenny's Journey into Investing
• (05:10) - Why did Jenny choose the investor side of the table?
• (08:27) - How did Jenny land her first investment (which went big!)?
• (11:02) - How does Jenny evaluate companies?
• (15:39) - How Jenny categorizes companies and check sizes
• (17:49) - How an angel investment went public and yet Jenny got nothing
• (25:18) - How does Jenny maintain authentic relationships while seed investing?
• (29:38) - Seed investors promise access to founders - does it matter?
• (33:39) - Jenny's successful seed investment in a Blockchain company - for real!
• (37:53) - Angel invest and chill? What signals help assess your investment early?
• (39:26) - How Jenny seed invests and then helps with future fundraising
• (40:46) - Using secondaries to generate returns and lower risk
• (44:18) - Pre-Seed fund return profiles - what's the goal and reality?
• (46:14) - Jenny and Everywhere seed invest in the "table stakes economy"
• (47:21) - What is the difference between pre-seed and seed startup investment rounds?
• (48:56) - Does valuation discipline matter for early angel and seed investors?
• (51:44) - Jenny's latest seed investment: Fora comes out of stealth
• (53:47) - Jenny's one trick to become better at startup investing
• (55:43) - How Jenny partners with Scott to make investment decisions
• (57:00) - Jenny's hot takes
• (58:21) - Takeaways from the interview

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We're all discussing current market conditions - valuations, AI hype, fundraising challenges... Before we kick off our planned interview series on First Funders, we sat down with our friend Arjun Arora to discuss the Trends in Venture Capital 2024. As investors, we always look ahead, making this a great way to start 2024.

Highlights from our discussion:

• What to expect in round sizes and valuations
• Anticipated returns from the AI hype
• The significance of data-driven decision-making for VCs
• The rise of hyper-specialized funds

You can read the full report here: https://www.arjundarora.com/trends-report

This is for information purposes only. This is not investment advice.

Topics

• (00:00) - 01: State of Venture Capital 2024 - Arjun Arora
• (00:49) - Guest: Arjun Arora on the State of Venture Capital 2024
• (01:24) - Arjun's Founder Background
• (03:03) - Format One and how they help founders
• (04:41) - Are Mega-deals only happening in AI?
• (06:07) - How should early-stage investors consider exit strategy?
• (08:02) - Is AI coming for venture capitalists?
• (10:36) - Social signals inform investors about founders AND teams
• (11:51) - Later-stage investors use prior investors as a signal
• (13:57) - Are crowd-funded companies legit investments?
• (16:01) - Do funds focused on a niche limit returns and increase risk?
• (22:25) - Don't go chasing Unicorns?
• (26:41) - Where's crypto and blockchain?
• (27:27) - Do founders want to do one-and-done raises?
• (29:17) - Can seed funds less power law, higher average outcomes?
• (31:45) - Will AI generate returns for investors?
• (33:35) - Advice for founders in this market environment
• (35:21) - Key Take aways: What we learned from Arjun's report for our own seed investing strategies
• (43:00) - Outro

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