Listen the full interview here 👇

Techstars founder David Cohen was an angel investor in Uber. He also had the chance to invest in Lyft — and passed.

Same market. Same timing. Two completely different outcomes in his portfolio.

The difference? At Uber, he met Ryan Graves (employee #1) at Techstars. “I really clicked with him.” He invested without ever meeting the Uber founders.

At Lyft, Matt Van Horn was a Techstars mentor. They were friends. But the idea seemed stupid: “Intercity transport for college kids? I didn’t get it.”

That same team pivoted, fast-followed Uber, and built a multi-billion dollar company.

After 20 years evaluating startups, the pattern behind his misses is always the same.

The Miss Framework: Why “Bad Ideas” Create Unicorns

The problem: We judge founders by their initial ideas, when ideas are what change the most.

The framework: There’s a Venn diagram that explains everything: “Seems like a bad idea” vs “Actually is a good idea.” The tiny overlap in the middle is where real money is made.

Why it works:

1. Uber and Airbnb were “stupid ideas” — No one wanted to ride in a stranger’s car. No one wanted to sleep in a stranger’s house. Today they’re worth hundreds of billions.

2. The idea blinds you to the team — When an idea seems so bad, you never get to properly evaluate the people. And the right people will pivot to something that works.

3. The market matters more than the idea — Cohen now asks: “Do you love the market? Because they’re probably staying in that market.” The specific idea will change. The market won’t.

The tactical shift:

Before: “Is this idea good?”
Now: “Do I love this team? Am I interested in this market?”

The lesson: Great teams can fix bad ideas. Great ideas can’t fix bad teams.

“The commonality in my passes is that they were ‘bad ideas.’ And there’s a Venn diagram I always remember: what seems like a bad idea, what actually is a good idea, and that tiny overlap in the middle — that’s where people make fortunes.”

This is the simplified framework, but David goes much deeper on how AI is changing founder evaluation (spoiler: technical talent matters less, market insight matters more), why he believes we’ll soon see “zero-employee unicorns,” and his contrarian take on why you DON’T need to be in San Francisco to build a world-class company.

🎧 Listen to the full episode: → [Spotify] → [Apple Podcasts] → [YouTube]

Also in this episode:

[15:50] – Why AI creates a “barbell effect” for startups — the middle gets stuck

[26:00] – How to scale networks without destroying them — segmentation is key

[31:30] – Techstars’ internal meme: “Replace ‘AI’ with ‘software’”

[38:35] – Why AI agents will do venture capital — and probably better than humans

[40:10] – Jack Bogle’s philosophy applied to VC: “The finance industry just subtracts value from society”

Instead of freezing, Freepik became one of the first major image platforms to integrate generative AI. Today, Freepik is one of the most widely used AI creative apps, according to a16z.

This is exactly how they did it.

The Playbook: Action First, Strategy Later

Most incumbents respond to disruption with endless analysis, committees, and 18-month plans. Joaquín did the opposite: he acted before having clarity.

1. Accept that you don’t have a plan (and act anyway)
When DALL·E 2 launched, Joaquín had COVID. Isolated, he spent 24 hours a day looking at AI-generated images. He came out of that period without a plan — but with one clear conviction: the existing business model was dead.

“When you don’t know what to do, do something instead of standing still. Every action teaches you something.”

Rather than waiting for clarity, he made a simple next move: put the technology in users’ hands and see what happened.

2. Use your distribution as a laboratory
Freepik had 600,000 subscribers. Instead of protecting the legacy business, they turned that audience into an experiment:

• They integrated Stable Diffusion 1.5 the day it launched

• They were the first major platform to do so

• They listened closely to what users asked for (history, visual styles, thumbnails)

• They iterated on what they could control and waited on what they couldn’t

Their existing distribution became a competitive advantage — not because it defended the old model, but because it accelerated learning about the new one.

3. Strategy emerged from action
Only after acting did Freepik truly understand its position:

• AI models quickly commoditize (many LLMs competing with each other)

• The real value sits in the wrapper: how the model is exposed to the world

• Freepik already had distribution and deep knowledge of creative users

“Strategy came after action. We started by reacting to users, and only then did we develop the strategy.”

4. Avoid self-deception about your ‘advantages’
Adobe, Shutterstock, and Getty fell into the same trap: they built comforting theses (“only we have copyright-safe images”) that turned out to be wrong. Their models were weaker because they restricted their training data.

Joaquín recognized the pattern: companies look for AI narratives that favor them instead of facing reality.

Freepik accepted that its millions of images were not a sufficient moat — and that freed them to compete on product, not protection.

“AI often forces you to rethink everything from scratch. And that’s very hard to do.”

This playbook isn’t about having all the answers. It’s about moving fast enough to find them before your competitors do.

Joaquín goes much deeper into how he handled conversations with his team (some needed psychological support), why he believes humans will remain essential in creative work, and the framework he uses to think about what AI will never be able to replace.

🎧 Listen to the full episode: → [Spotify] → [Apple Podcasts] → [YouTube]

Also in this episode:

[10:00] Why launching AI without a clear strategy beat staying frozen

[23:00] The “Humans vs AI” framework and what machines will never replicate

[31:00] The hardest conversations with artists who thought their careers were over

[45:00] The strategic mistake that made Adobe, Getty, and Shutterstock fall behind on AI

[58:00] Why distribution is a temporary advantage, not a real moat

[01:00:00] How building Freepik from Málaga—not Silicon Valley—became a competitive edge

Manny’s path took him from a shrimp farm in Ecuador to the heights of Silicon Valley, where he built Outreach into a $4.4B SaaS. But in 2023, a conversation with the CEO of DocuSign handed Manny a “Red Pill” moment: if AI agents do the work of humans, companies will hire fewer people, and the seat-based SaaS model will collapse .

He realized the current infrastructure—giants like Salesforce, Netsuite, and Datadog—was “conspiring against him.” They could track closed deals or API calls, but they couldn’t distinguish between an agent’s cost (tokens) and its value (reasoning) .

Manny founded Paid to solve this: a way to interpret agent behavior so builders can stop selling cheap software and start selling valuable work. Paid has raised +$30M from investors like Sequoia, Lightspeed and EQT.

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🗒 What we covered:

[13:00] – How the tech recession forced Outreach to reinvent itself

[18:30] – Why seat-based pricing is dead and what replaces it

[34:00] – Why the Agent Economy is impossible without a new metering layer

[45:30] – Why generalist agents lose to specific domain experts

🧠 Big Ideas

#1 Tech Is a Great Starting Market, But a Terrible Place to Stay

Outreach grew by selling seat-based SaaS to tech companies. But when the market crashed and those companies cut staff, Outreach’s revenue stalled overnight. He realized tech gives you PMF, not durability. Founders must ask: Is my business built on early adopters, or on industries that survive downturns? If you want a long-term company, your revenue has to cross the chasm long before you think you need to.

#2 The Question from DocuSign’s CEO That Proved Seat-Based SaaS Is Dead

DocuSign CEO told Manny: “If your agents work, why would I hire more people next year?” That single sentence exposed the flaw behind the entire SaaS model. If headcount shrinks, seats shrink. If seats based pricing shrink, SaaS dies. Founders building AI products must stop pricing like old software. The future is not per-seat, it’s per outcome.

#3 The 10× Opportunity: Ultra-Vertical Agents That Replace Salaries, Not Seats

Manny argues that the real AI opportunity isn’t general-purpose agents, it’s vertical agents that perform specific workflows so well they replace human headcount. And when an agent replaces five SDRs or automates a mortgage workflow, it isn’t a $49/mo seat, it’s a slice of payroll. That shift from IT budgets to labor budgets is what makes the agent economy a 10× larger market than SaaS.

😲 My Favorite Quote:

“At Outreach I was paying fortunes to Zuora, Salesforce, and Netsuite, yet it felt like those systems were working against me. The status quo wasn’t neutral; it was my enemy. It was in my face, laughing, taking money out of my pocket, and reminding me I couldn’t do anything about it.

And when you get that kind of punch in the mouth, something changes. That taste of blood wakes you up. You stop thinking in terms of market opportunities and start thinking in terms of refusing to feel powerless again. You promise yourself you won’t get hit like that anymore, and you begin fixing what those systems will never let you solve.”

Prior to FJ Labs, Fabrice built multiple companies including Zingy, which he scaled from near bankruptcy into a $200M exit, and OLX, which he grew to 300M users across +40 countries, before it was acquired by Naspers.

Today he runs FJ Labs as an “angel investor at venture scale,” evaluating hundreds of deals a week and backing 150–200 startups a year with a fast, founder-friendly process.

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🗒 Show notes:

[01:00] – Why being a public company CEO stopped being interesting
[22:00] – Will AI kill marketplaces? The real impact on e-commerce
[27:00] –The next big play: buying offline businesses and 10x’ing them with AI

[33:00] – The trillion-dollar opportunity in B2B digitization
[49:00] – Do AI startups really need less capital?

🧠 Key Takeaways

#1 Stop Chasing “Success” If You Hate Your Tuesdays

Fabrice built a massive company, reached financial freedom, and won his market, yet felt miserable. He realized success isn’t about scale or recognition, but whether your daily work energizes you. His “life audit” forces founders to ask: Do I still enjoy the work this success demands? If not, the business isn’t the problem, the role is.

#2 Why AI’s Biggest Wins Will Come From Unsexy B2B Workflows

Fabrice argues the real AI gold mine isn’t in flashy verticals but in the offline, analog processes that run the global economy. Factories, suppliers, logistics, marketplaces, and procurement still rely on emails, spreadsheets, and phone calls. AI will create the most value by modernizing these slow, invisible workflows, not by reinventing consumer apps.

#3 Don’t Compete in “The Game of Kings”: Play a Vertical You Can Actually Win

Founders outside Silicon Valley shouldn’t compete with OpenAI, or Google on foundational models, they lack capital, talent, and infrastructure. The winnable path is going deep in a specific vertical, owning its workflows, and using AI to make them better. Investors should avoid infrastructure fantasies and back applied-AI companies with real customers and real problems.

#4 AI Won’t Kill Marketplaces—Because Shopping Is Human, Not Logical

Fabrice argues GPT won’t replace ecommerce because people don’t just search, they browse, discover, and entertain themselves. And the messy backend of fulfillment, payments, and logistics is something AI won’t own. Marketplaces aren’t dying; they’re getting augmented.

😲You won’t hear this anywhere else

“Most investors think of AI as a race to replace human labor, but the reality on the ground looks very different. When I look at how companies are deploying AI, I don’t see mass layoffs. I see teams hiring even more engineers to build better products, faster. Technology has always made work cheaper and more efficient, yet historically it has created more jobs, not fewer.

The real value isn’t in removing people, but in reshaping roles: AI handles the diagnosis, the doctor provides empathy; AI delivers the lesson, the teacher becomes a guide. The shift will be profound, but it will unfold far more slowly than people expect and its ultimate impact will be far greater than we imagine.”

Born in Buenos Aires and raised in the US, Marcelo’s career took him from finance at J.P. Morgan (where he invested in Mercado Libre) to Funny or Die, a comedy startup backed by Will Ferrell, and later to Real Influence, a platform that connected brands with YouTubers long before influencer marketing was mainstream.

Today, he’s building Evalion, a testing and monitoring platform for voice AI agents, based on the belief that in the near future millions of companies will build their own agents, as voice becomes the primary interface for how we interact with technology.

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🗒 Show notes:

[10:30] – The moment Marcelo realized you can’t outcompete Google.

[11:48] – How Ipsy started: turning creators’ attention into a business model

[23:00] – Founder–market fit vs. curiosity-driven founders

[26:10] – Why passion for the process matters more than passion for the industry

[32:40] – Voice as the next interface: from websites → apps → agents

[48:40] – Building Evalion: why trust and reliability will be the next real moat in AI.

🧠 Key Takeaways

#1 Curiosity as the Real Founder Superpower

Marcelo didn’t start companies because he lived with the problem, he did it out of pure curiosity. At Ipsy, that mindset helped him see how creators, brands, and supply chains connected before the “creator economy” existed. Now in AI, that same drive pushes him to understand how voice tech is built from scratch.

#2 The Next Platform Shift: Voice
Marcelo has seen every interface shift: web, mobile, and social. Now, with Evalion, he’s betting on voice as the next one. As AI gets better, people will talk to brands instead of typing, and each company will need its own “voice identity.” The screen won’t vanish, it’ll merge with conversation. Those designing for voice-first today will lead tomorrow.

#3 The Reliability Moat: Why Trust Is the Next Advantage in AI
Evalion is building the reliability layer for voice agents, testing and monitoring how they perform. Marcelo believes trust will matter more than intelligence as AI scales. Just like Datadog became essential for cloud reliability, AI will need its own backbone for consistency. The real opportunity isn’t making AI smarter, but making it dependable.

😲You won’t hear this anywhere else

“Most people think the future of conversational AI will be dominated by a few giants like OpenAI or Google. But I see a world with millions of builders creating their own voice agents. It’s not that different from what happened with the web or mobile apps.

At first, everyone thought Yahoo would build every website, but that never happened. Companies will want to build their own voice experiences because they’re the direct interface with their customers.

You won’t talk to ChatGPT to book a flight with United; you’ll talk directly to United, through a personalized voice that reflects its brand. When that happens, human–machine interaction will fundamentally change. We’ll move from looking down at our phones to a world where screens are everywhere and voice is omnipresent.”

Shawn led early investments in Uber, Roku, Siri, and Chime, generating over $2 billion in returns for Menlo’s limited partners.

Behind those wins is a clear philosophy, what Shawn calls his Consumer Utilitarian Framework: a model for backing companies that use breakthrough technologies to meet timeless human needs in faster, cheaper, and better ways.

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🗒 Show notes:

[16:20] — His Consumer Utilitarian Framework and Menlo Ventures’ 4 investing pillars.

[20:10] — Core principles: timeless human needs × evolving technology.

[22:06] — AI as the next “ingredient technology” unlocking new markets.

[38:20] — How AI gives apps like MyFitnessPal a second life

[56:20] — Shawn’s key lessons from 20+ years of consumer investing.

🧠 Key Takeaways

#1 The Consumer Investor’s Mindset: Shawn reframes consumer investing through Maslow’s hierarchy of needs. He argues that human behavior has barely changed in 100,000 years, what changes are the “ingredient technologies” (like AI) that unlock new ways to meet the same timeless needs: safety, belonging, self-expression, mastery, etc. Don’t chase trends or viral behaviors. Anchor your product in a permanent human job-to-be-done. Then ask: “What new technology now makes it 10x better, faster, or cheaper to meet that same need?

#2 Delight is a leading indicator, but not a moat: Shawn describes his process as starting from emotional intuition, moments when a product feels “magical”, but quickly layering on analytical discipline. Many investors stop at delight; he goes further to test whether delight connects to a repeatable, scalable business model.
Emotional resonance gets you noticed; operational excellence keeps you alive. Founders should design for delight, but validate for durability, ask what real problem it solves, how often it repeats, and how the economics scale beyond the early adopter bubble.

#3 AI will turn every personal habit into a market: Shawn predicts that AI will unlock entire consumer categories that failed before because they demanded too much user effort, nutrition tracking, fitness planning, time management, personal CRM, relationships.

These “failed apps” (like MyFitnessPal, Evernote, or Salesforce) are now viable again because AI removes the friction between intent and action.
Revisit old consumer pain points that once looked “too boring” or “too hard to scale.” AI transforms friction into opportunity. A product that used to require constant manual input can now anticipate, auto-complete, and coach.

😲You won’t hear this anywhere else

“We talk about AI like it’s going to make us infinitely productive, but maybe that’s not what we actually need. We’ve had decades of productivity gains from the internet, from mobile, from every app that promised to ‘save time’and yet people seem more stressed, more distracted, less connected. Maybe what’s missing isn’t more output, but better rails for how we live. Technology that doesn’t just accelerate work, but helps us pause, recognize when we’re overwhelmed, nudges us to take a break, or reminds us to be present with each other.

If AI could give us that—tools that restore empathy and awareness instead of eroding them it would be the most important shift of all. Not more productivity, but more humanity.”

Pablo studied industrial engineering and pursued a Ph.D. in computer vision in Munich. Alongside his brother Javier Palafox (COO) and Luis Paarup (CTO), they were part of Y Combinator’s in 2023, where they pivoted from their initial idea to what Happy Robot is today.

Recently, Happy Robot raised $44M in its Series B, led by funds like Base10 and a16z. Their “Forward Deployed Engineering” approach allowed them to grow their revenue 20x since their Series A. Today, they work with over 100 clients, including the largest freight brokerage firms in the U.S.

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Today, Pablo and I talked about:

• Why implementation is more important than technology.

• How to get your clients to see you as an “AI partner” instead of just a vendor.

• How the “Forward Deployed Engineering” model drove their 20x growth.

• How they went from being a “threat” to a “strength” for their clients.

• Why building a blame-free culture is essential when working with imperfect technology.

🤯 Key Insight: The key to automating traditional industries lies in proper implementation.

While most AI startups sell demos over Zoom, Pablo understood that to transform a traditional industry, the solution couldn’t be 100% remote.

His bet was Forward Deployed Engineering (FDE). This partner-implementer model solves the biggest barrier to adoption: the human factor. By working from the inside, AI stops being perceived as an external “threat” and becomes an internal “strength,” validated by the team itself. This approach helped them grow 20x since their Series A.

⭐ Favorite Quote: “The truth is, customers don’t want an AI vendor; they want an AI partner. Someone who is willing to go the extra mile to understand their use case and make it work.

It’s fascinating to see how they go from viewing us as a threat in their SWOT analysis to considering us a strategic opportunity in just one year. It’s not just about implementing technology; it’s about guiding them through the transformation of how they work.”

🤔 Fun Fact: Before founding Happy Robot, Pablo dedicated 19 years of his life to the piano, reaching a near-professional level. His teacher wanted him to pursue a musical career, but despite his talent, he chose to study industrial engineering.

Interestingly, this musical discipline taught him about perseverance and commitment, qualities he now applies as the CEO of his startup. He admits he would probably repeat the same approach with his own children because of the valuable lessons it taught him.

I learned a lot from Pablo. Follow him on LinkedIn for more ideas and advice.

Before Sendgrid, Isaac started multiple startups that failed and faced a ton of challenges as a first time founder, with very little business background and an introverted personality.

Today, we discussed Isaac’s challenges in transitioning from founder to CEO, his decision to bring in an external CEO to SendGrid, and the lessons he learned along the way. We also covered the company-building lessons he gained at SendGrid, including insights on product development, market timing, and team building.

Finally, we talked about his latest venture, Memo, and how he aims to empower introverts to build their personal brands and social capital in a world dominated by social media.

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🗒 Show notes:

[04:01] - How did Isaac decide to bring in an external CEO

[09:18] - Transition from founder to becoming a CEO

[19:01] - The role of the founder

[29:51] - Business lessons from SendGrid's success

[51:19] - What does it mean to build a social network platform for introverts

🧠 Key Takeaways

#1 Hire Your Boss: Isaac knew early on he wasn’t the ideal long-term CEO, preferring to focus on product development. Supported by mentors and being the transparent with the board, he successfully transitioned leadership to Jim Franklin, who shared the company’s core values and mentored Isaac, ensuring both his growth and SendGrid’s success.

#2 Building a Strong Foundation: Isaac emphasized the importance of a great team, mentors, and clear values. He learned that even with a solid team and funding, success isn't guaranteed. Mentors help navigate unknown challenges, and strong values guide decisions when mentors can't. 

#3 Empowering the Quiet Majority: Isaac's Memo is a social network for introverts, tackling the issue that 90% of social media content is created by 10% of users. Memo focuses on meaningful connections, allowing users to be found on their terms, prioritizing user control and privacy over invasive engagement tactics.

#3 Empowering the Quiet Majority: Isaac's Memo is a social network for introverts, addressing the issue that 90% of social media content is created by 10% of users. Memo focuses on meaningful connections, allowing users to be found on their terms, prioritizing user control and privacy over invasive engagement tactics.

😲You won’t hear this anywhere else

[About hiring an external CEO] “I think I would start with the end: hire your boss. You need to see this person as your boss, even though you created the company and have many ideas. Ultimately, they need the ability to make the decisions required for a CEO.

Accepting this makes everything easier. A smart CEO will always seek the founder's opinion, especially on gut feelings. Founders have the best gut instincts for their company by far. If CEOs leverage this, you can create a great relationship where the founder feels included in decisions.”

Before Valor, Paulo played a protagonic role in developing LatAm’s growth equity ecosystem as a Managing Partner at SoftBank, managing their $8 billion LatAm Fund. Paulo invested and acted as a board member of several Brazilian unicorns including VTEX, Loggi and Creditas. He also invested over a decade in Latin America’s public and private equities at Third Point Management and Eton Park.

In this episode, we talked about the non-obvious investing principles he’s learned over his career, why he’s bullish on LatAm’s venture and growth ecosystem, unlike other investors, and his reflections from his time at Softbank. We also discussed his frameworks for investing in growth-stage companies in Brazil and LatAm, including markets, regulatory tailwinds, business models, metrics, and teams; and how this has changed since 2020 and 2021.

Learn about investing principles in growth-stage companies today:

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🗒 Show notes:

[02:15] - Transitioning from Private to Public Investments

[05:48] - Understanding the Dynamics of Private Equity and Venture Capital

[07:56] - Insights into LatAm’s Growth Ecosystem

[11:55] - Reflecting on Investment Lessons and Market Dynamics

[22:18] - The Role of Local vs. Global Investors in LatAm

[29:31] - Regulatory Changes and the Rise of Fintech in Brazil

[39:11] - Rethinking Business Models and Capital Efficiency

[55:18] - The Impact of AI on Business Models

🧠 Key Takeaways

#1 Adapt for Local Success: The companies that succeed in LatAm are the ones who don't think about the other countries' success cases, but companies that tailor their strategies to local regulations, taxation, logistics, theft issues, and income levels. Copying models from the U.S. or Europe can be counterproductive. 

#2 Don’t Try to Win Every Deal: As an investor, you’ve got to be losing deals, almost as a ‘sanity’ check for knowing that you're doing the right thing. There’s something to be calibrated with your risk appetite and valuation analysis if you put out 10 term sheets in a year and every single term sheet is accepted.

#3 How AI Will Shape the Venture Industry: Producing code is going to get cheaper, and the barrier to entry will be lowered, making it more challenging to maintain margins and protect excess economic profits. Investors might need to get involved in software companies at an earlier stage (up to Series B), as companies will become profitable sooner and need less external capital. Although this dynamic affects pure digital goods, like fintech and software companies, other types of businesses will still require capital.

😲You won’t hear this anywhere else

What challenges do founders face when transitioning from startup growth to scaling a company, and how can they address them?

“It's common for them to take a company from zero to one hundred, but not necessarily from one hundred to one thousand. This transition can be problematic and often traumatic. Founders might either manage to step out gracefully or inadvertently destroy value during the process. Some founders are versatile enough to handle the entire journey, but it's rare.

Most founders believe they are versatile, but the truth often proves otherwise. Realizing this sooner allows them to move to an executive chairman position and hire a capable CEO. This mindset should trickle down, with continuous upgrades at the C-level being necessary. Although it's a ruthless and challenging process, it's essential for the company's growth."

Kevin has had a long and respected career in Data Science and AI, serving as Uber’s first head of data science and inventing Uber's dynamic pricing feature. Before Rackhouse, he was the Chief Data Officer of Tala Financial, advised several VC firms, and personally supported over 50 companies as an angel investor.

Today, we discussed all aspects of AI investing, from identifying when data and AI are core to a business model to distinguishing between wrappers and new applications. We also talked about the common characteristics of industries most ripe for AI solutions. In addition, we explored how AI will shape the future of company formation and the venture capital industry itself.

Learn about the strategic application of AI in investment and industry today:

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🗒 Show notes:

[02:01] Kevin's Journey From Working in Academia to Joining the Tech Industry

[05:25] Early Exposure to Big Data, and How Transformative Technologies Like Transformers Are

[15:13] Founding of Rackhouse and Kevin’s Investment Strategy 

[20:57] Detailed Insights into How AI is Reshaping Decision-making Processes.

[30:07] Evaluation of Market Trends and Hype 

[35:00] The Future of AI and Business Models 

[53:28] Advice for Entrepreneurs and Investors

🧠 Key Takeaways

#1 Truly data-driven companies distinguish themselves by understanding and influencing how their customers use data to make decisions. This involves in-depth market and customer research to pinpoint how improvements in data quality or execution can significantly impact procurement decisions, especially in industries burdened with legacy systems and numerous vendors.

#2 As an investor, one must be cautious with industries that are trendy due to data-related trends. For example, skepticism in the Web3 space stems from the fact that high token prices do not guarantee better AI execution. This selective approach avoids markets where data is less likely to be a key decision factor.

#3 In B2B SaaS, the belief has always been that you need one standout feature that's 10x better than everything else. However, an uncommon pattern is that founders often work on two or three medium-value features and stack them together. Kevin found that the same applies to LLMs, especially in co-pilots. There's no real need to migrate everything in your workflow. Good co-pilots naturally integrate with a seamless UX, allowing you to switch contexts effortlessly. It is possible to achieve product-market fit by accumulating a variety of use cases, even if none of them is 10x.

Prefer working with companies that excel in their core vision, which naturally attracts market and business opportunities. This straightforward strategy is particularly effective in environments where adding complexities like AI, extensive marketing, or insider knowledge does not align with the company’s strengths or market effectiveness.

😲You won’t hear this anywhere else

Kevin Novak discusses an investment in a company that is innovating in predictive modeling, particularly for railway safety. He explains:

"In predictive modeling, we face a stark reality: you can't wait for 10,000 trains to derail to collect enough data to prevent future accidents. They only had about 60 photos of cracked wheels from actual derailments. The solution? They’ve developed the ability to synthetically create images of potential defects, which experts can then review and validate for authenticity. Combining these synthetic images with our few real ones, we've created an incredibly effective predictive vision system. This breakthrough in synthetic data technology is opening doors for industries that sparse datasets have traditionally hindered."

Rodrigo Baer is a Managing Partner and co-founder at Upload Ventures. He began investing in Brazilian startups in 2010, then became a Managing Director for Redpoint eventures and a Partner at SoftBank's Early Stage fund for LatAm. He has invested in over 6 unicorns, including iFood, CargoX, and Pismo.

Today, we discussed the history and trends of Brazil´s venture ecosystem, the lessons he has learned from investing in multiple unicorns, why he decided to start his own fund after a decade, and his approach to helping startups. 

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🗒 Show notes:

[09:35] - Which were the most important stages of the Brazilian startup ecosystem

[26:00] - Lessons from Rodrigo's journey as an investor

[36:55] - Insights on how VCs make investment decisions

[38:40] - Building successful founder-investor relationships

[42:05] - What founders should ask from investors

[47:42] - What will be the next startup stage in LatAm from Rodrigo´s POV

🧠 Key Takeaways

• Identify what's not contributing to your growth: in your startup journey, this is an important skill. When something isn't working, you're faced with a pivotal decision: should you stop this activity because it’s not essential, or is it so critical that you need more resources to fix it. For example, how you are positioning your company or which markets you should be going after. This is not just about cutting losses; it’s about strategic redirection towards effective outcomes.

• Great investors have tough conversations with founders: your investors are not there just to point out challenges like when your conversion rates are low, your sales tactics aren’t hitting the mark, or your cash burn is alarmingly high but to help you navigate these tough decisions. Having these hard conversations is essential, not optional. The idea is to analyze their numbers, understand the core issues, and decide whether to pivot or persevere.

• Prioritize efficiency, but be aware of when it’s important to do so: As you transition from developing your product to scaling your business, consider carefully assessing where to assign your resources. Instead of rapidly expanding your team, you might start small and perfect your sales process with a few key players before considering a larger team. This strategy minimizes confusion and ensures that each step is focused on achieving your business objectives.

😲You won’t hear this anywhere else

“In the fast-paced world of startups, timing isn't just about speed; it's about synchronization. Aligning your startup's milestones with market readiness and investor interest is crucial. Remember, a well-timed move can mean capitalizing on an opportunity and missing the boat entirely. Always stay attuned to the market's pulse—this will guide you when to push forward and hold back, ensuring your venture's growth is rapid and right on schedule.”

Over a year ago, David wrote “The Non-Obvious Emerging LP Playbook”, which has become one of the best blog posts on the somewhat obscure world of Limited Partners, the money behind the Venture Capital industry. 

Since then, David has become one of the best community builders in Silicon Valley, focused on helping emerging Limited Partners think and invest like the most established Limited Partners. David also hosts a fabulous podcast called Superclusters, focused on demystifying the world of Limited Partners.

Learn about emerging LPs today:

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🗒 Show notes:

[09:20] - WTH Are Emerging LPs?

[25:48] - Why it's So Hard to Access Big Funds

[36:33] - Product Market Fit For Funds

[45:32] - Your Response Rate Can Win You Deals

[49:56] - Funds Can Pivot Too

[54:12] - What It Means to Be Specialized

🧠 Key Takeaways

#1 Be Prepared to Educate Them: Emerging LPs are in very different segments: high net-worth individuals, family offices, fund of funds, IRAs, etc. What they have in common is that they have little to no exposure to the world of Venture Capital and want to learn about it. Be willing to answer questions every week and put time into helping them, because that is one thing you can provide that the Sequoias of the world don’t have time to. 

#2 Don’t Over-Sell Your Results: If you’re pitching that your fund has 110% IRR on paper, that might impress emerging LPs, but maintaining that expectation in reality won’t be possible. A better approach would be to be realistic with your metrics and upfront with what worked and didn’t work. This will help you gain their trust.

#3 How You Communicate Matters: As a GP, you want to “win” LPs over. One way to do that is to be consistent with your communications. If you say you’ll update them once a month, keep that promise and always send the email on time. And when they contact you, be sure to respond in the least amount of time possible. If you keep them waiting, they may think you’ve lost interest in them and start looking elsewhere. 

😲You won’t hear this anywhere else

“Should a fund be pivoting? There are some LPs that say, ‘no, they should never pivot. They pitched me a 10-15 year strategy, and they should stick to it’. And there are other folks like, ‘how do you predict what's going to happen in 10-15 years?’. In my opinion, funds pivoting is okay. If you were able to predict what happens 10-15 years from now, you would make so much money, and be a freaking genie.

That said, if you do want to pivot, I think there should be preemptive communication. You should first tell your LPs ‘I'm seeing the market grow and move in that direction, so we want to bet 10-20% of the strategy on that. Are you okay with it?’, and then execute the pivot. But, keep it at 20% max. If you need to pivot more than 20% of your fund, you either should give that money back and raise a new fund on a new strategy, or limit your exposure because there's a lot of shiny object mentality in venture.”

This week I talked to Sean Salas from Camino Financial to understand the Latino market in the US, how the business model of Camino works to allow them to serve micro businesses, and the lessons he has learned about building a company and fulfilling his vision.

Through technology and AI, Camino offers affordable loans to satisfy the demand for credit that rises to 20 billion dollars from Latino micro and small businesses. They raised over 150 million dollars of debt and equity funding, and in 2023 they merged with Fundation, an SMB tech-enabled lender and specialist in bank channel partnerships.

Learn about the US Latino market today:

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🗒 Show notes:

[02:46] - The Power of the US Latino Market

[07:40] - What You Don’t Know About This Market

[15:20] - Latino Only, Yes or No?

[22:55] - The Broccoli-Flan Paradox

[44:38] - The Big Expensive Bet in Fintech

[49:32] - A B2B Strategy is Key

🧠 Key Takeaways

#1 You need a Latino strategy: In the US, the Latino market is growing faster than any other market. For this reason, it is important to cater to this segment in your strategies, with products or programs meant for them. Now, this doesn’t mean that you must exclusively serve Latinos, but merely include them. Products that service this market can drive considerable growth to a business. And, because it is an underserved market, it can also drive loyalty towards a company that thinks about them. 

#2 Don’t do only B2B: Going directly to businesses is a strategy that lowers the CAC and increases revenue. However, it can also create an exclusively transactional relationship between business and client without loyalty. To prevent this, it’s best to combine it with a B2C strategy to reach people directly and build loyalty with them. This creates a flywheel where the consumers are acquired through the businesses, making both strategies feed one another.

#3 The winning credit strategy: most underwriting is done considering traditional documents like tax returns and salary slips. This makes it difficult to evaluate the creditworthiness of people who may be self-employed or have fluctuating income for a variety of reasons. To solve this issue, you can look at alternate documents like the transactions they do in their bank accounts to try and estimate their income. This is widely used in emerging markets but could be used more in the US to offer financial products to underserved populations, such as immigrants.

😲You won’t hear this anywhere else

“We did a lot to really drive financial literacy and education. But, particularly in credit, they try to force-feed these financial tools and resources to clients as a condition for getting the credit. And the cold hard truth is that this is like force-feeding them broccoli. And the flan is the capital. As a small business owner, we’re living with very limited bandwidth, so sometimes we want the flan before we eat our broccoli, even if we know the broccoli is important. With this dynamic, extending a value proposition with education is really hard to do. We have tried incentive structures to make the broccoli more attractive and call it chocolate-covered broccoli, but those opportunities are still a work in progress. It’s not easy.”

However, the idea of merging these modern educational models with traditional universities seemed far-fetched until recently.

With over 120k paid subscribers and 1M users, Alura made headlines by acquiring FIAP, a well-known private technology university in Brazil. 

This move was a strategic step towards offering comprehensive courses and in-person classes complementing their online programs.

Today I sat with Paulo Silveira, Alura’s founder, to understand the reasoning behind acquiring a traditional university, why online education can’t grow as fast as SaaS, how to balance rapid growth with the quality of learning, and whether startups will actually be able to disrupt traditional universities.

Spotify | YouTube | Apple Podcasts

🗒 Show notes:

[12:11] - You Can’t Blitzscale Education

[23:31] - How to Merge Cultures

[30:28] - The Importance of Reputation

[38:49] - Don’t Get Addicted to Ads

[47:14] - Communities are NOT Leads

[55:51] - Why AI Doesn’t Threat Universities

🧠 Key Takeaways

#1 The B2C>B2B Flywheel: It is possible to service both consumers and businesses and create a situation where one feeds the other constantly, especially in education. In the example of Alura, they teach individuals and when they see that several people work in the same company, they reach out to the company for a deal. Since the employees advocate for it, the sale is much easier. But if they had only focused on B2B, they would have to directly sell to the C-levels and prove their value. 

#2 Create something bigger than your startup: Content marketing is a cheaper alternative to paid ads, that also keeps delivering results even years later. However, the content has to go beyond your brand. Don’t create to let others know how great your brand is. Create to help others, regardless of whether they’re clients or not. This is why Paulo’s podcast is called Hipsters.tech instead of Aluracast, as many people around him suggested. His podcast is not only for clients, it’s for anyone who wants to learn about tech.

#3 Blitzscaling can hurt you: In Venture Capital, growth at all costs tends to be common, so startups get used to high CAC and higher ad spend. But the speed of growth can get addicting, and when you want to slow down and start looking for profitability instead, it can feel like a mistake. Ads are still a good tool, but they shouldn’t be a primary acquisition channel. Make sure you can still grow, even if you cut down on ad spend as a way to help achieve profitability.

😲You won’t hear this anywhere else

“I don’t think AI generating content automatically is a game-changer. With the human in the loop, it does give you leverage, but not if it’s by itself. And I don’t think it’s true that everyone will learn through conversational AI either. When students are enrolling, it’s not exactly because there is not enough content, especially written ones, or because they want to learn from a bot. They want a person teaching them because they know the course. They need clear direction. AI can be an assistance to universities, but shouldn’t be overused.”

Other mentions:

• The article mentioned in the episode: A Future With Only 10 Universities (hackeducation.com)

But behind the scenes, the payment ecosystem is a thing of nightmares, with tech stacks built in the 90s, dozens of different companies mashed together, and waiting 18 hours just to see if a piece of code works. 

Today’s guest has a habit of explaining how the payment ecosystem works at any opportunity he gets. 

Richie Serna co-founded Finix, a fintech that started as a payment infrastructure startup and gradually expanded into facilitating and processing payments. Finix has built its tech stack from scratch, which allows it to connect directly with any credit card network in the US market, where four payment processors have 80% of the entire market share with technology from the 90s.

Richie and I talked about all things payments, the product insights he gained from the industry’s history, Finix's business model evolution from enabling vertical SaaS to becoming a payment processor, and how payments will shape the future of software.

To date, Finix has raised more than 130 million dollars and processes tens of billions of dollars in payments.

Learn about fintech and payments today:

Spotify | YouTube | Apple Podcasts

🗒 Show notes:

[3:08] - How Paying for Your Nike Shoes Works

[13:11] - Why Payments Are a Black Box

[24:06] - Play Your Money Well

[34:45] - Take the Android Approach

[42:02] - How to Focus on the Right Thing

[59:18] - Payments Will Change SaaS

🧠 Key Takeaways

#1 Explain it in a Napkin: Presentations are the worst way to explain anything. Your audience is trying to decipher the slides and figure out how the different components integrate when they should be listening to you. Instead, explain it by drawing on a napkin or a whiteboard (depending on the setting of the conversation). That way, people can follow your reasoning as you speak, and don’t get distracted by information on the slide that you haven’t said yet. 

#2 Know Your Industry’s History Inside and Out: Many things that seem broken now, have a reason to be the way they are. There’s a method to the madness. If you want to be able to fix it, you first need to understand its history. Study your industry deeply to understand how it came to be the way it is, and the solutions might come a little more easily to you.

#3 How to Prioritize: This simple process helps you decide what is worth your focus in your current stage:

• Number the options of features and products you have

• For each, calculate how much money and time it’ll take

• Then, think about the unknowns that would make each one harder than it sounds

• Look for people who tried it before and failed, and ask them what you’re missing

• If you’re fundraising, how much will each option help you with your fundraising story? 

😲You won’t hear this anywhere else

“Fintech has been this hot space for the last few years. But when I first got into payments in 2013, with the first startup I worked for, we struggled for well over a year to raise our Series A, and we were neck to neck with Stripe. In Hacker News, it was always us versus Stripe, and we were beating them consistently, we clearly had a better product. I talked to investors and they said ‘How many fintech companies have gone public? How many had massive exits? The last big one was Paypal in 2002’. There were so many barriers for people to be successful, that fintech as a whole hadn’t really been proved out. Then Stripe, Plaid, and a bunch of other companies started having success and more money started rolling in.”

Elias co-founded Drift, a software platform that helps over 50,000 businesses like Okta and Adobe deliver personalized conversations with their customers. Drift reached unicorn status in 2021 when private equity firm Vista Equity Partners acquired a majority stake.

We also discussed the future of the SaaS industry, why he believes product defensibility is no longer feasible, and how to think about building a SaaS business in this context, including the implications of AI. 

Before Drift, Elias spent a decade at IBM, founded Performable, which was acquired by HubSpot, and became VP of Engineering for HubSpot following the acquisition. Currently, he is building Novy, a team specializing in developing and deploying cutting-edge AI solutions.

Learn about the lessons of founding a unicorn startup here:

Spotify | YouTube | Apple Podcasts

🗒 Show notes:

[08:13] - The Biggest Dichotomy 

[16:47] - What Is Your Notion of Risk?

[22:21] - Step #1 to Become Successful

[29:37] - The Dichotomy of Product Differentiation

[33:45] - Copy Others AND Be Yourself

[40:22] - Advice for SaaS Founders Today

🧠 Key Takeaways

#1 Take more risks: Define clearly what the risk of a decision is and the consequences it can have for you. This exercise can help you see if the decision is as risky as it looked at first glance, or if the stakes are lower than you thought. For example, if you’re risking losing your house or visa, be careful when deciding. But if you’re risking having to find another job and think you can find a new one, then the risk might not be as high.

#2 Be comfortable with conflicting ideas: Sometimes as a founder, you hear conflicting advice about the same thing, but it’s not that one is right and the other is wrong. Both are right, and you have to figure out how they fit together. For example, in SaaS, you hear that product differentiation is essential for success, and you hear that it is not. What this means is that your product needs to be different to succeed, but that alone won’t lead to success, you need more differentiating elements to get there.

#3 Follow the advice: Sometimes people ask for advice when they only want encouragement and stories. While encouragement is important, taking action on the advice is more helpful to succeed. If the advice makes sense to you, take action and see where it takes you. You can judge if it was good advice or not, based on the results. 

😲You won’t hear this anywhere else

“Copy the product, because you don’t waste time. That way you get started, practice and you have something to show. That way you learn about the problem and how other people solve it.  And then, you have to figure out how you make it different and find your own way to succeed. The world is too crowded with businesses, so you have to differentiate yourself.”

The Power Law, the renowned book on the history of Venture Capital, has an entire chapter dedicated to the story of how Kevin Efrusy “found” Facebook.

This week I sat down with Kevin to understand what a prepared mind is in Venture, how investing in Facebook shaped his investment philosophy and him personally, and why he has been dedicating more time to philanthropy rather than venture capital.

Kevin joined Accel Partners in 2003 and was the lead investor in companies like Groupon, Couchbase, and Facebook. He also began Accel's Latin America initiatives, leading to investments in Despegar, Gympass, Nuvemshop, and Quinto Andar. A long-time advocate for LatAm's startup ecosystem, Kevin has invested in leading regional venture funds Kaszek and Monashees and has supported numerous founders.

Learn about his philosophy for investing today:

Spotify | YouTube | Apple Podcasts

🗒 Show notes:

[15:40] The Cycles of the Technology Business

[18:04] - What’s The Prepared Mind 

[22:44] - Why Facebook Crushed Their Competition

[43:07] - There’s No Single Way to do Venture Capital

[44:16] - How the Mediocre Venture Capitalists Do It

[48:33] - Why Focus on Latin America?

[52:24] - Transferable Skills Between VC and Philanthropy

[58:13] - Is VC the Right Model for Latin America?

🧠 Key Takeaways

#1 The Prepared Mind: In this practice, you ask yourself:

• What are you looking for? 

• What do you think will happen in the next few years? 

• What do you think the next set of brilliant companies will be?

• What will make them successful?

The idea is to prime your brain to recognize opportunities that match your predictions so you can prepare to act on them. Kevin did this around what the next internet would be like, and it helped him recognize the potential of Facebook. He then persisted in investing in the company, even when it wasn't open to investors.

#2 The intuition is most important: Kevin points out that many people want to ask the consumer what they want and then build a product around that. But the consumers don’t know what they want, so they can’t tell you, and you end up with a terrible product. Instead, Kevin suggests that you need to have a point of view and develop your product around it. This point of view needs to look different and be a little scary to have the potential to be incredible.

#3 How to make up for a small market: Kevin pointed out that if you dominate a particular market and become the #1 player, market size won’t prevent you from having a good business. He also stated that the entire LatAm market is only a fraction of the US, so there is not enough market share for several competitors to thrive. Because of this, Kevin recommends that other funds invest in later rounds of the existing companies in a market. If they invest in various companies in the same market, none will dominate it.

😲You won’t hear this anywhere else

“A typical young person who gets into Venture Capital wants to know: ‘How do I become a partner in the firm? What do I need to do to ‘succeed’?’. They think: ‘I need to make investments, one of those has to work, and hopefully I don’t lose any money.’ But that’s how they keep doing these bad deals. They never make the great ones because those are scary. 

My advice to young people in jobs looking to get promoted is ‘Don’t try to get promoted.' Instead, focus on doing amazing stuff. If you focus on what you believe is amazing, everything else will work out. If you do something just because you think it’s what your boss wants, it won't work. If you’re not doing something where you’re a little afraid that you might get fired, then you’re probably not doing anything interesting.”

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