Episode 36: From scaling Carta to $300M ARR to showing you how the rich stay tax-free and build generational wealth.

Alessandro Chesser helped build Carta from zero to $300M+ ARR as their first sales hire—before walking away to start Dynasty, they make billionaire-level wealth tools accessible to everyone. In this episode, we dig into the playbook behind Carta’s early sales engine, the contrarian pivot to B2C, the growth loops powering Dynasty, and why Alessandro believes most Americans are getting screwed by the current wealth system. If you’re a founder or GTM operator, this one’s packed with battle-tested lessons, failures, and play-by-play stories.

Key Discussion Points:

🔥 What's the secret to selling a product that doesn't exist yet?

🤝 How to build a sales team that can sell the future, not just the present

🚀 The importance of prototyping and iterating quickly to meet customer needs

📈 Why most founders get sales wrong and how to avoid common pitfalls

💡 The surprising way to get customers to commit to a product that's still in development

📊 How to measure the success of a sales approach that's focused on the future

🚫 The biggest mistake founders make when trying to scale their sales team

Timecodes:

0:00 - Introduction

2:00 - 0 to $300M: Inside Carta’s Sales Machine

7:19 - Building relationships with early adopters and positioning them as design partners

14:06 - Building trust and promoting from within in a team

29:05 - Understanding dynasty trusts and their benefits

36:54 - Leveraging AI for SaaS scaling and customer support

44:29 - Cold email marketing strategies and organic content creation

47:00 - Closing remarks

Important links:

Dynasty: https://www.getdynasty.com

Struggling to come up with ideas to write on social - Jerry: https://tryjerry.com

Quirky startup merch: Shop71 at https://shop.7tea1.com

I'm joined by Moksh Garg, Co-founder & CEO of Figr, an AI-powered design platform that helps design teams and product teams design and build products faster. Moksh shares insights on complex workflows, enterprise product design, and productivity boosts. Moksh also talks about the challenges of scaling a design system for large and complex products, and how Figr can help extract design systems from Figma and convert them into HTML code.

Key Discussion Points:

🔍 Design teams waste 75% of their time on repetitive tasks: How Figr can help

📊 Complex workflows: Understanding the challenges of scaling design systems

💡 AI-powered design platform: How Figr uses AI to boost productivity

🔍 Figma plugins: Generating design systems from scratch and extracting design systems from existing designs

💡 Measuring user interactions and iterating on product design

🚀 Building a design tool using a multi-agent workflow

📊 Data quality and synthetic data: Training specialized models

P.S. If you enjoy conversations about #entrepreneurship and #startups follow me for more!

Important links:

Figr: https://figr.design/

Struggle coming up with ideas to write on LinkedIn - Jerry: https://tryjerry.com

Quirky startup merch: Shop71 at https://shop.7tea1.com

In this episode, I'm joined by Ka Ling Wu, Co-Founder of Upsolve AI, a customer-facing analytics platform. Ka shares her background in rugby, working at Palantir, and more. We dive into Upsolve's mission to help companies build and offer analytics to their customers, using AI to create hyper-personalized dashboards. Ka also discusses the challenges of scaling from 0 to 20 customers, including overcoming the high bar of embedding components in SaaS products and building trust with founders.

We talk about:

🏉 The rugby life and startups

📊 Upsolve's mission: Building and offering analytics to customers using AI

🚀 Scaling from 0 to 20 customers: Challenges and lessons learned

🤝 The value of the YC experience and finding the right founding team

And more!

P.S. If you enjoy conversations about #entrepreneurship and #startups follow me for more!

Important links:

Upsolve AI: https://www.upsolve.ai/

Struggle coming up with ideas to write on LinkedIn - Jerry: https://tryjerry.com

Quirky startup merch: Shop71 at https://shop.7tea1.com

In this conversation, I’m joined by Axel Aigret 🚀 — serial entrepreneur, product strategist, and now founder of StorytoDoc.ai. Axel has spent 15+ years building SaaS that doesn’t just work, but *wows*.

From selling ecommerce startups to leading immersive VR health tech, he now helps SaaS teams ship user-loved documentation, automatically.

We dig into:

🧠 Why your *idea* isn’t the problem — your *approach* is

📖 The genius of turning product usage into documentation (via AI!)

👀 How to get real user feedback without falling into the interview trap

📹 The system Axel uses to record, summarize, and *share* product thinking

💡 The counterintuitive way to find clarity: ship fast, reflect faster

If you’re a founder trying to go from “cool idea” to “real product” — this one’s for you.

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P.S. Know someone launching a SaaS product? Send this their way. 👇

#VenturingWithVishesh #founderbrand #saasfounders

Follow me @visheshd for more stories at the intersection of tech, strategy, and execution.

Important links:

StorytoDoc: https://www.storytodoc.ai/

Struggle coming up with ideas to write on LinkedIn - Jerry: https://tryjerry.com

Quirky startup merch: Shop71 at https://shop.7tea1.com

This time, I’m joined by Sam Shames, the co-founder and COO of Embr Labs, an MIT-born startup that’s creating a whole new category of wearable tech—personal temperature regulation. Sam’s journey is a masterclass in building hardware startups that survive, scale, and serve a deeply underserved audience.

We talk about:

🔥 Inventing a wearable that heats and cools

👩‍🦳 Solving real pain for the thermally underserved (think menopause, MS, dysautonomia)

🧪 What 4 years of R&D before Kickstarter taught them

🚀 A subscription model that unlocked $4M ARR in 8 months

🧭 What most hardware founders get wrong about manufacturing

This episode is packed with real, tactical insights on building category-defining hardware, finding PMF, staying alive when others fold, and navigating the messy middle of hardware + subscription + software.

Important links:

Embr Labs: https://embrlabs.com/

Shop 71: https://shop.7tea1.com

In this episode, I’m joined by Ohad Biron, Co-Founder & CEO of Bagel AI, a product intelligence platform that helps product managers bridge the gap between product and revenue. Ohad brings 18 years of experience at the intersection of R&D and business, having scaled startups from pre-revenue to multi-million ARR.

We dive into:

🔍 Why Product and Go-To-Market Teams Are Often Misaligned

📊 Lessons from Founder-Led Sales

🛡️ How to Build Trust and Close Deals in a Skeptical Market

🏗 How to Build a Strong GTM Motion Without a Huge Budget

🔥 The Reality of Selling AI to Enterprise Customers

🎯 How Bagel AI is Automating Product Insights to Reduce Churn & Improve Onboarding

This episode is packed with tactical insights for founders building B2B SaaS, especially if you're trying to find product-market fit, align product with revenue, or scale your sales motion efficiently.

Important Links

Bagel AI - https://getbagel.com

Quirky Startup Merch https://shop.7tea1.com

AI is consuming the internet—scraping content, generating responses, and reshaping how we search for and interact with information. But there's a massive problem: who gets paid?

In this episode, I sit down with Hirsh Pithadia, CEO & Co-founder of Valyu Networks, to discuss how content creators, publishers, and businesses can monetize their data in the age of AI.

We talk about:

🔍 The AI Monetization Problem: How LLMs consume content without compensating creators
💰 The Future of Search: Why search engines are dying, and what comes next
📈 The Business Model Shift: From training data licensing to context enrichment
🛠 Valyu’s Solution: Building monetization rails for AI-generated responses
🚀 Startup Fundraising Stories: How an accidental meeting with a16z led to funding
🤖 AI-Generated Data & Model Collapse: What happens when models train on AI-generated content?
🌍 US vs. Europe for AI Startups: Why Hirsh believes scaling in the US is crucial
🎯 Advice for Founders: How to navigate and build in a fast-moving industry

This is a must-listen if you're a founder, AI enthusiast, or anyone thinking about the future of data, monetization, and AI business models.

Important Links:

https://www.valyu.network/

In this episode, I sit down with Michael Bak, Head of Investor Relations at TechBBQ, founder of Nordic Investor Day, and a key player in shaping the Nordic startup ecosystem. With over 15 years of experience building communities and fostering investor-startup relationships, Michael shares the hidden rules of fundraising and building startup ecosystems.

We talk about:

🌍 The rise of Copenhagen’s startup ecosystem and what makes it unique

🔥 How TechBBQ went from a grassroots initiative to a 10,000-person event

🤝 How investors evaluate founders beyond pitch decks

💡 Why trust is the #1 currency in fundraising (and how to build it)

🎯 How founders can avoid wasting time with the wrong investors

🚀 Insider tips on networking and making the most of startup events

This episode is packed with fundraising strategies, investor psychology, and practical event networking hacks that will help you build the right relationships and raise capital faster.

You can connect with Michael at https://www.linkedin.com/in/michaelbak/

Find more about TechBBQ at https://techbbq.dk/

This week, I’m joined by Duke Vu, co-founder & CEO of Fungies.io, a platform helping Indie SaaS and Game Developers sell globally without the headaches of payments, taxes, or compliance.

Duke shares his journey from startup failures to big wins. We also talk about fundraising, scaling, and finding the right co-founder—without sugarcoating the hard parts.

If you’re an indie founder looking to sell smarter and scale faster, this episode is for you.

Important Links:

https://fungies.io

In this episode, I’m joined by Mario Tarouca, co-founder of FrameDrop, a company that started by helping Twitch streamers automatically clip and repurpose their content but is now making a bold pivot from B2C to B2B.

Mario shares his entrepreneurial journey, including the challenges of scaling a B2C SaaS product, and how his team identified a bigger B2B opportunity in media and broadcasting.

We talk about:

🎮 The origins of FrameDrop

📉 B2C SaaS struggles

🔄 How FrameDrop found a major pain point in media companies

⚡ Why speed is crucial when making a major shift

🛠️ How FrameDrop leveraged organic traffic to scale its B2C product

💰 How investors view iterations and pivots

This episode is packed with insights for founders navigating pivots, customer discovery, and growth—whether you're in SaaS, media, or any other industry.

Important Links:

FramedropAI - https://framedrop.ai