I'm joined by Gautam Rishi, the Co-Founder & CEO of OneShot.ai, a pioneering AI-powered sales development platform. With a background in tech and a passion for innovation, Gautam has led OneShot from its early days to a successful company that's changing the face of sales development. In this conversation, we dive deep into the challenges of sales development in the AI era and explore practical strategies for building successful sales teams.
This episode explores the challenges of sales development in today's AI-driven landscape, highlighting the importance of human touch and listening skills in building successful sales teams. Gautam Rishi shares his journey from a successful tech career to founding OneShot, discussing the impact of AI on the sales development representative industry and how his company positioned itself in the market before the AI boom.
Key Discussion Points:
🔥 Why most salespeople fail: The surprising truth about AI implementation
🤖 The lost art of listening: How human touch can revive sales in AI times
📊 Reviving human touch in AI-driven sales: The hybrid approach that worked
🚀 The surprising impact of technology on sales skills: What's being lost
👥 The rise of young entrepreneurs: How they're changing the sales landscape
💼 The importance of hiring the right talent: What to look for in a sales team
📈 Focus on one or two marketing channels: The secret to successful outbound marketing
Timecodes:
0:00 - Introduction
1:00 - The Journey from SDR to Founder
5:00 - Identifying the Problem in the SDR Industry
8:00 - The Impact of AI on Outbound Sales
11:00 - Navigating Early Success and Market Changes
14:00 - The Shift from Email to Phone Outreach
17:00 - Hiring Fractional SDRs: Benefits and Challenges
20:00 - Building a Hybrid Sales Model
23:00 - The Importance of Human Element in Sales
26:00 - Addressing the Skills Gap in Modern Sales Teams
29:00 - The Role of Curiosity and Self-Improvement in Sales
32:00 - Understanding Customer Needs Through Outbound
35:00 - Common GTM Mistakes Startups Make
38:00 - Pre and Post Product-Market Fit Strategies
41:00 - Aligning Engineering and Sales Goals
44:00 - Incentivizing Engineers for Better Alignment
47:00 - The Importance of Resilience in Startups
50:00 - Final Thoughts for Founders
52:00 - Where to Find Gautam and OneShot.ai
Important Links:
You can reach Gautam Rishi at https://www.linkedin.com/in/grishi
Vishesh, your host at https://vishesh.space
Checkout OneShot.ai
P.S. If you are writing on LinkedIn https://tryjerry.com
I'm joined by Ananya Grover, Founder of HealCycle, a Labouisse Fellow, and Entrepreneur-in-Residence at Antler. With a background in public health and a passion for women's health, Ananya has dedicated her career to developing innovative solutions for women's health and wellness.
This episode explores the intersection of hormonal and mental health, discussing the importance of emotional support and personalized insights for women dealing with premenstrual symptoms and conditions like PMDD. Ananya shares her journey in founding HealCycle, a hormone and mood tracking app, and emphasizes the need for a holistic approach to women's health.
Key Discussion Points:
🔥 What happens when hormonal and mental health intersect?
🤯 The surprising connection between PMS and PMDD
💡 How AI can help support women's mental health
📊 The importance of personalized user experiences in health tech
👥 The role of community building in mental health support
💻 The challenges of developing AI companions for mental health
🚀 The future of women's health technology and its potential impact
Timecodes:
0:00 - Introduction
0:15 - The Spark Behind HealCycle: Ananya's Journey
5:55 - The Importance of Hormonal Tracking in Women's Health
8:16 - Product Design Choices: Addressing Serious Health Concerns
10:51 - HealCycle's Global Reach: User Demographics
12:03 - Differentiating HealCycle from Competitors
14:55 - Building the First 100 Users: Strategies and Insights
20:34 - Safeguarding Users: AI Companion Ethics
23:08 - Balancing Warmth and Guidance in AI Interactions
25:40 - Learning from Failures: Distribution Challenges
27:12 - User Onboarding: Cultural Considerations
30:06 - Direct-to-Consumer Strategy: Insights on Healthcare Distribution
32:39 - Exploring Partnerships with Healthcare Professionals
35:38 - Future Directions: Habit Change and Health Coaching
36:59 - Current Challenges: Growth and Retention
37:18 - Lessons Learned: Growth Hacks and Mistakes
38:37 - Never Get A Cold Email
41:23 - Closing Remarks and Where to Find HealCycle
Important Links:
You can reach Ananya Grover at https://www.linkedin.com/in/ananya-grover
Vishesh, your host at https://vishesh.space
Checkout HealCycle at https://www.healcycle.com/
P.S. If you are writing on LinkedIn https://tryjerry.com
I'm joined by Jasmine Bonder, the Chief Executive Officer of Clinova.Solutions, a healthcare technology company that's revolutionizing patient care. With a background as an ICU nurse practitioner, Jasmine brings a unique perspective to the intersection of healthcare and entrepreneurship.This episode explores the intersection of healthcare and entrepreneurship, highlighting the importance of patient-initiated care and the need for innovation in medical treatments. Jasmine Bonder shares her journey from ICU nurse practitioner to CEO of Clinova.Solutions, emphasizing the importance of understanding product-market fit and regulatory compliance in healthcare startups.Key Discussion Points:🔥 What's the biggest misconception about transitioning from healthcare to entrepreneurship?🤝 How can healthcare startups prioritize patient-initiated care and improve access to medical treatments?🚀 What are the unique challenges of beta testing in healthcare, and how can startups overcome them?🌎 How can healthcare startups navigate regulatory environments and expand globally?🤖 What role does AI play in healthcare, and how can startups leverage it for innovation?💡 What's the most important lesson Jasmine Bonder has learned as a nurse entrepreneur, and how can others apply it to their own journeys?Timecodes:0:00 - Introduction1:00 - From ICU Nurse to Entrepreneur: Jasmine's Journey5:00 - The Challenges of Patient Decision-Making in Healthcare7:00 - Gaps in Med Tech Launches: What Founders Need to Know11:00 - Defining Scope of Practice in Asynchronous Care13:00 - Scaling Clinova: Serving All 50 States15:00 - Pricing Strategies for Medical Devices17:00 - Product-Market Fit Challenges for Startups19:00 - Importance of Patient Feedback in Product Development21:00 - The Role of AI in Healthcare: Opportunities and Limitations23:00 - Nurse Capital: Supporting Nurse Entrepreneurs25:00 - The Rise of Nursing Entrepreneurship Post-COVID29:00 - Daily Life of a Nurse Entrepreneur: Balancing Act31:00 - Key Obstacles in Scaling Healthcare Tech33:00 - Advice for International Founders Entering the US Market35:00 - Collaborating with Clinicians: Navigating Conflicts of Interest37:00 - Final Thoughts: The Heart of Health Tech EntrepreneurshipImportant Links:You can reach Jasmine Bonder at https://www.linkedin.com/in/jasmine-bonder-67b3a827a/Vishesh, your host at https://vishesh.spaceCheckout Clinova.Solutions at https://www.clinova.solutions/P.S. If you are writing on LinkedIn https://tryjerry.com
I'm joined by Will Betteridge, the Founder and CEO of Fair, a pioneering auto warranty company that has achieved $2M ARR. With a background in creative pursuits, Will has brought a unique perspective to the tech world, leveraging his experiences at Uber Eats and TikTok to drive growth and innovation at Fair.
From humble beginnings in hospital parking lots to achieving $2M ARR, Will Betteridge shares the blueprint for lean growth of his startup, FairWarranty. He reveals the surprising insights and unique perspectives that helped him navigate the auto warranty industry, build a successful business, and overcome the challenges of scaling.
Key Discussion Points:
🔥 What inspired a creative person to leave the world of fashion photography and graphic design for the tech world?
📊 Fascination with the auto warranty industry and why?
🚗 What are the unique challenges of the auto warranty industry, and how did Will overcome them?
💸 How did FairWarranty evolve its go-to-market strategy from direct consumer sales to a B2B approach?
📈 What role did strategic pricing and positioning play in driving conversion rates for FairWarranty?
🤝 How did Will build strong partnerships and establish trust in the warranty industry?
💡 What are the key takeaways for founders looking to build a successful business in a non-AI space?
Timecodes:
0:00 - Introduction
1:10 - Background: From Uber Eats to TikTok and Beyond
7:10 - The Journey to Founding Fair Warranty
10:00 - What Fair Warranty Does: A Deep Dive
12:00 - Go-To-Market Strategy: From Direct Sales to Partnerships
14:20 - Pricing Strategy: Balancing Value and Trust
16:00 - Vertical Integration in the Auto Warranty Industry
18:30 - Leveraging Cash Flow: The Importance of Float
21:40 - Identifying Valuable Distribution Channels
25:00 - Maintaining Competitive Advantage in a Crowded Market
27:00 - The Importance of Branding and Trust
31:00 - Fundraising Insights: Cold Outreach and Building Relationships
35:00 - Future Plans: Integrating AI and Machine Learning
38:00 - Quickfire Questions: Recommendations and Lessons
40:00 - Closing Remarks and How to Connect
Important Links:
You can reach Will Betteridge at https://www.linkedin.com/in/wbbetteridge/
Vishesh, your host at https://vishesh.space
Checkout Fair at https://fairwarranty.com
P.S. If you are writing on LinkedIn https://tryjerry.com
I'm joined by Kat Wendelstadt, Growth Angel at Ada Ventures, a seasoned expert in go-to-market strategies and customer engagement. With a background in big tech and a passion for startup growth, Kat has helped numerous companies refine their messaging and scale their marketing efforts. She's also a thought leader in the space, frequently sharing her insights on the importance of empathy and curiosity in customer interactions.
Effective go-to-market strategies for early-stage startups require a deep understanding of customer needs and pain points. By refining messaging and testing across various channels, startups can achieve significant conversion uplifts and scale their marketing efforts. In this episode, we explore the critical mistakes to avoid and innovative approaches to winning customers and impressing investors on a tight budget.
Key Discussion Points:
🔥 What's the most common mistake early-stage startups make when it comes to go-to-market strategies?
🤔 How can you ensure your messaging resonates with your target audience and drives conversions?
💡 What are some innovative approaches to customer engagement and content generation that don't break the bank?
🚀 How can you identify the most impactful marketing channels for your buyer's journey and scale your efforts?
📊 What are the key metrics to track and measure when it comes to go-to-market strategies, and how can you optimize for success?
Chapters:
0:00 - Introduction
2:08 - GTM Pre-Series A
6:21 - The 5 Cardinal Sins of Early-Stage GTM
7:21 - Messaging Fixes that Drive Growth
10:15 - Cutting Through the AI Noise
11:09 - Category Creation and Storytelling
16:23 - Low-Budget GTM Tactics for Startups
20:17 - The Attribution Challenge in 2025
22:18 - Choosing the Right GTM Channels
25:27 - Sales-Led vs PLG Motions
28:43 - GTM Challenges During a Pivot
32:14 - Overhyped Channels and Declining Reach
35:22 - Building Repeatable GTM Systems
39:53 - Bonus Segment: Fun Questions with Kat
42:42 - Must-Read GTM Book for Founders
43:12 - Where to Follow Kat Wendelstadt
Important Links:
Kat Wendelstadt (Guest)
- https://www.linkedin.com/in/kat-wendelstadt-gtm
- https://www.katwendelstadt.com/
Vishesh Duggar (Host)
- https://www.linkedin.com/in/visheshd/
- https://vishesh.space
- https://tryjerry.com
I’m joined today by Peter Cooper. He has spent 25+ years leading security transformations across high-stakes industries like fintech, banking, and critical infrastructure. From scaling global teams at Adyen to navigating compliance across IPOs and banking licenses, Peter now helps early-stage and growth companies build pragmatic, trust-first security. This episode explores what founders can learn from enterprise mistakes, how to bake security into culture, and why checklists won’t save you.
We talk about:
We talk about:
🛡️ When to not hire a CISO — and what to do instead
🔍 How top founders evaluate security at each stage of the startup journey
🚫 The difference between security theater vs real resilience
📈 Why every founder should define their risk appetite before they scale
👨👩👧👦 How to build “self-healing” security culture in early-stage teams
⚙️ The surprising truth about SOC2 tools like Vanta and more
🧠 Peter’s 6-phase security maturity model from Ideation to IPO
💸 Security metrics that actually matter — including how to reduce spend over time
⚖️ Compliance vs Trust — and why one won’t save you
💥 Real-world founder mistakes that triggered breaches
This episode is a must-listen for any founder navigating fundraising, customer trust, or scaling product with peace of mind. Especially if you’re non-technical — Peter explains it all without buzzwords or scare tactics.
P.S. Know a founder who thinks “we’ll worry about security later”? Share this.
#VenturingwithVishesh
For more raw conversations on #startups, #SaaS, and founder-led growth, follow @visheshd
Important Links:
You can reach Peter at: https://www.linkedin.com/in/petercoopercv/
Vishesh, your host at https://vishesh.space
P.S. If you are writing on LinkedIn https://tryjerry.com
Chapters
0:00 - Peter’s Background: From Adyen to Fractional CISO
2:00 - What Startups Get Wrong About Security
4:07 - Why Security Is Often Reactive, Not Proactive
6:15 - Misconceptions Around Compliance and SOC2
9:12 - Security Debt vs Technical Debt
12:10 - The Culture Layer of Security
15:22 - Security Theater in Startups
17:50 - When to Hire a CISO (and When Not To)
21:05 - Security Responsibilities in Early Teams
23:48 - Peter’s 6-Phase Security Maturity Model
27:15 - What “Minimum Viable Security” Looks Like
30:20 - Evaluating Vanta, Drata, and AI-Compliance Tools
33:42 - Reducing Friction for Engineers
36:10 - Key Security Metrics That Actually Matter
38:55 - Common Founder Blind Spots
41:00 - Advice for Non-Technical Founders
43:05 - The Biggest Security Mistake Peter Ever Saw
45:40 - Final Takeaways for SaaS Founders
In this episode, I’m joined by Liam Collins — founder of Proxis (YC S24), your enterprise AI sales email autopilot. Liam’s built AI agents that behave like 24/7 interns, scaling cold email personalization and follow-ups without burning out your sales team.
But Proxis wasn’t born overnight. From prior auth in healthcare to devtools for model distillation, Liam's founder journey is packed with pivots, painful feedback loops, and deep technical execution.
We talk about:
🤖 The architecture behind Proxis’ AI email agents
📬 The reality of inbox challenges in true enterprise sales for reps — and how Proxis handles it
📉 Lessons from Proxis’ pivots — from healthcare to fine-tuning to sales automation
🚨 Edge cases they didn't think about
🧪 Why dogfooding your GTM is the fastest way to ship better
🌍 What slowmadding across 20+ countries taught Liam about discipline and play
💬 How to balance founder-led engineering with founder-led sales
📈 What most sales outreach gets wrong — and how Proxis keeps it human
This episode is for any founder who’s grappling with sales at scale — especially if you're early-stage, running lean, and tired of the copy-paste chaos of cold outreach.
Important Links:
Turn your enterprise's inbox on autopilot with Proxis: https://proxis.ai
Vishesh, your host at https://vishesh.space
P.S. If you are writing on LinkedIn https://tryjerry.com
I'm joined by Alex M H Smith, Founder of Basic Arts, with a background in developing innovative business strategies and a passion for helping entrepreneurs succeed.
Most startups are strategically bankrupt, meaning they lack a clear strategy, leading to generic and undifferentiated businesses. To succeed, founders need to develop a strategic hypothesis and create a differentiated choice. This requires a deep understanding of the market, competitors, and customer needs.
Key Discussion Points:
🔥 What's the biggest issue with most business strategy advice?
🤔 How can founders create a differentiated choice in a crowded market?
📝 What's the importance of writing a strategy document for business success?
🚀 How can innovation be used to fix issues in a category?
📊 What's the relationship between value creation and business success?
📈 How can founders find leverage in the market by focusing on competitors rather than customers?
Chapters
00:00 The Flaws in Business Strategy Advice
02:02 When Founders Should Seek Strategic Help
04:50 The Importance of Differentiation in Strategy
07:59 Developing a Strategic Hypothesis
11:40 Creating Unique Value for Customers
14:11 The Role of Branding in Strategy
17:45 Leveraging Competitors for Strategic Insights
23:21 The Power of Differentiation
26:15 Identifying Strategic Advantages
32:15 Content-Led Growth Strategies
46:12 The Essence of Giving in Strategy
Important Links:
https://www.linkedin.com/in/alex-m-h-smith
https://basicarts.org
https://www.linkedin.com/in/visheshd/
https://vishesh.space
Episode 42, I'm joined by Griffin Parry, the Founder and CEO of m3ter, a billing infrastructure company that helps software businesses drive revenue growth through usage-based pricing. This episode explores the transformative journey of a successful entrepreneur who exited his business to Amazon Web Services (AWS) and shares valuable insights on building a successful startup, navigating the challenges of usage-based pricing, and creating a billing infrastructure that drives revenue growth.Timecodes:0:00 - Introduction1:46 - The Memo That Changed His Career: Streaming Before It Was Obvious3:50 - Bootstrapping GameSparks and Raising Along the Way4:43 - Why AWS Acquired His Startup7:33 - Life After Acquisition: From CEO to AWS Employee11:22 - Bringing Amazon’s Culture DNA to M3ter13:53 - Can You Copy Culture? Lessons from AWS and Netflix16:43 - The Problem with Usage-Based Pricing in SaaS22:58 - How They Recruited Design Partners Before Writing Any Code23:47 - Opportunity Cost vs. Operational Excellence31:44 - Making Remote Work: Onboarding, Meetups, and Radical Candor38:44 - From Manual Outbound to Industrialized GTM Engine47:21 - Closing remarks🎙️ Subscribe for more episodes!#Episode42 #VenturingWithVishesh #Startups #Entrepreneurship #startups #entrepreneurship #venturingwithvishesh
Important links
https://m3ter.com
https://vishesh.space
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
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
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
