Venturing with Vishesh — Startup Founder Interviews on SaaS, AI, Fundraising & Venture Capital.

I'm joined by Sudarshan Kamath, the Founder of smallest.ai, a research lab that aims to prove that smaller models can achieve intelligence. With a background in AI research, Sudarshan has led smallest.ai to develop custom voice agents for large enterprises, achieving the fastest voice agent in the world.

This episode explores the challenges of building successful voice agents for enterprises and how Smallest.ai achieved the fastest voice agent in the world. The conversation delves into the importance of treating voice agents like humans, with room for improvement and scaling.

Key Discussion Points:

🔥 What's causing the high latency, costs, and poor quality of voice agents for enterprises?

🤖 Why treating voice agents like humans is crucial for success

📈 How Smallest.ai achieved the fastest voice agent in the world

🚀 Why most founders get AI implementation completely wrong

📊 How to measure what's growing in the company and stay focused

Important Links

LinkedIn

https://www.linkedin.com/in/sudarshankamath

https://www.linkedin.com/in/visheshd/

https://smallest.ai - Voice AI Suite for Enterprises

https://tryjerry.com - The Warm Outbound Engine. For your lean sales teams who want to grow without scraping, spamming, or risking their LinkedIn account.

I'm joined by Shubham Choudhary, co-founder and CTO of FirstWork (YC S24), who is using his extensive experience at Rippling and Deel to reshape the frontline HR tech space. In this episode, we unpack how he’s using agentic AI, a custom rules engine, and battle-tested global compliance experience to outpace incumbents with lean teams and real-time automation — all while closing enterprise AI pilots at scale.

Timecodes:

0:00 - Introduction

1:06 - What is FirstWork and Why Build It Now?

11:01 - Lessons from Scaling Global Products at Rippling and Deel

19:20 - Why YC Asked FirstWork to Hire Fast

20:02 - Rippling's ‘Under-One-Roof’ Model Applied to Frontline HR

23:12 - Hiring Anxiety and the Case for Delegation

26:05 - Using AI for Validation Over Generation in HR Use Cases

29:38 - Enterprise Pilots: AI + SOPs → Fast Iteration

36:46 - Hiring Lessons from Deel, Rippling, and Startup #1

49:55 - FirstWork’s Sprint Cadence and No-Ceremony Culture

51:10 - Rapid Fire: Advice, Book, Product, and ChatGPT as Co-Pilot

56:00 - How to Reach Shubham and Closing Remarks

Important links:

FirstWork: https://www.firstwork.com/

Inbound-led-outbound motion made easy for LinkedIn without breaking their terms of service. - Jerry: https://tryjerry.com

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

🎙️ Subscribe for more episodes!

#Episode40 #VenturingWithVishesh #Startups #Entrepreneurship #startups #entrepreneurship #venturingwithvishesh

I'm joined by Zach Shefska, President & Chief Executive Officer of CarEdge, a pioneering SaaS company in the auto industry.

With a background in YouTube content creation and a passion for building community, Zach has led CarEdge from a small startup to a successful business with millions of dollars in revenue.

He's a true innovator in the space, and I'm excited to share his insights and experiences with you.

This episode explores the journey of building a successful SaaS business from a YouTube channel, highlighting the importance of community building, trust, and scaling. We dive into the challenges of transitioning from a YouTube channel to a SaaS product, leveraging influencer marketing, and navigating the auto industry landscape.

Key Discussion Points:

🔥 How a YouTube channel became a $10M ARR business: The surprising journey

🤝 Building trust and community through authentic content and relationships

🚀 Scaling a business in the auto industry: Lessons from a pioneer

📊 The power of influencer marketing in driving demand and growth

📈 The challenges and opportunities of transitioning business models

🚗 Navigating the complexities of the auto industry: Insights from a founder who's been there

📊 Measuring success and growth: Key metrics and strategies for SaaS businesses

Important links:

CarEdge: https://www.caredge.com/

Jerry helps founders who want to turn content into warm leads — without spammy DMs or breaking LinkedIn ToS (terms of service). Run an inbound-led outbound motion with authenticity, not automation. You can check it out at tryjerry.com.

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

I'm joined by Neel Balar, Co-Founder at Clueso (YC W23). Starting with 2 of his co-founders Akash and Prajwal in the final year at IIT Madras, Neel has led Clueso from a note-taking tool for students to a successful B2B SaaS startup serving 350+ B2B customers worldwide. Clueso helps product teams create stunning product videos and documentation in minutes.

Key Discussion Points:

🔥 How did you scale to 200+ B2B customers without any employees?

🤔 What's the secret to maintaining a global footprint with a small team?

📈 How did you manage to acquire new customers for your B2B SaaS startup?

📊 What's the key to building a successful team and ensuring everyone is aligned with the company's goals?

📈 What's the surprising content format that 10x'd your conversion rate?

📊 How did you navigate the challenges of building a roadmap, prioritizing features, and cutting features that no longer align with goals?

Important links:

Clueso - Create stunning product videos and documentation in minutes: https://www.clueso.io/

Build Inbound-led-outbound motion on LinkedIn without breaking it's terms - Jerry: https://tryjerry.com

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

I'm joined by Nicolai Thomson, Co-Founder & CEO of Jenesys, a company that's pioneering the use of AI in bookkeeping and cash flow management. With an impressive track record of selling B2B solutions across three continents and scaling companies from startup to multi-million pound revenue, Nicolai brings two decades of business wisdom to our conversation.

Key Discussion Points:

🔥 Cash flow works in a similar way to traffic flow - if you wait until the moment where all the cash is going out, you might actually find that you don't have enough, despite the fact that you've got a profitable business.

📊 Effective cash flow management requires you to proactively manage and slow down the cash flow, rather than waiting until the last minute.

🚨 I'm too scared to grow, that's a major, major problem in the industry - entrepreneurs need to overcome their fear of growth to achieve success.

💡 The only identifier on your phone that doesn't change is your wifi and mac address - what does this mean for entrepreneurs and business owners?

👥 Giving people an opportunity to create their best work is crucial for business success - how can entrepreneurs create this environment?

📈 The importance of involving the whole team in strategy changes and enabling team members to handle tactics is essential for scaling a company.

🤖 The risks of relying too heavily on AI for creativity and the importance of human foundation in engineering are crucial for entrepreneurs to consider.

Important links:

Jenesys: https://www.jenesys.co/

Inbound-led=outbound done right - Jerry: https://tryjerry.com

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

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.

---

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