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

Episode 51 with Santosh Sharan, Co-Founder & CEO at ZeerAI.I'm joined by Santosh Sharan, Co-Founder & CEO of ZeerAI, a pioneer in AI-driven go-to-market strategies. With a background in engineering and a passion for innovation, Santosh has led ZeerAI from its early days to a successful SaaS company. In this conversation, we dive deep into the challenges of building a successful SaaS business, discuss the impact of AI on go-to-market strategies, and explore practical strategies for SaaS founders navigating the changing landscape.In this episode, we explore the future of SaaS and the impact of AI on business models, customer acquisition costs, and the sales process. We discuss the importance of smart automation, unique data strategies, and community building to create a competitive moat.Key Discussion Points:🔥 Why most SaaS founders get AI implementation completely wrong🤖 The surprising way AI is changing the sales process📈 How to create a competitive moat in the SaaS landscape💡 The importance of unique data strategies in SaaS business models👥 How community building can drive customer acquisition and retention🚀 The future of SaaS and the impact of AI on customer acquisition costs💻 Why traditional CRM systems are no longer effective in the AI eraTimecodes:0:00 - Introduction1:00 - Santosh's Journey from Engineer to Founder3:15 - The Importance of Staying in One Industry5:00 - Learning Curve and Career Optimization7:30 - Overview of Zeer and Its Mission9:45 - The Shift in Go-To-Market Strategies12:00 - Challenges in Building a Two-Sided Marketplace14:30 - The Evolution of Product Development with AI17:00 - Impact of AI on Customer Acquisition Costs20:00 - The Future of SaaS: Legacy vs. New Players22:30 - Organizational Changes in the Age of AI25:00 - Hiring Strategies for AI-Driven Companies28:15 - The Role of Junior Employees in the Future Workforce30:45 - Learning Beyond the Job: A New Mindset33:00 - Go-To-Market Strategies: PLG vs. Sales-Led38:00 - Understanding Buyer Needs in Sales40:30 - The Role of Content in Buyer Engagement41:30 - Inspirational Reads and Philosophy42:30 - Closing Remarks and How to Connect with SantoshImportant Links:You can reach Santosh Sharan at https://www.linkedin.com/in/ssharanVishesh, your host at https://vishesh.spaceCheckout ZeerAI at https://zeer.aiP.S. If you are writing on LinkedIn https://tryjerry.com🎙️ Subscribe for more episodes!#Episode51 #VenturingWithVishesh #Startups #Entrepreneurship #startups #entrepreneurship #venturingwithvishesh

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 do most AISDRs fail?

🤖 How human touch can revive sales in AI times

👥 The rise of young entrepreneurs: How they're changing the sales landscape

🚀 Channels to focus on in B2B Sales

And more!

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