Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

This week, Josh sits down with Stephen Calhoun, CEO of Technical Visionaries — the team building SASI, an AI safety middleware layer that acts as an airlock between users and the AI chatbots they're talking to. Stephen is on his 4th startup. The other three failed. He opens up about why AI needs the equivalent of Norton or McAfee, the yacht-software startup he lost because he didn't get the contracts in writing, and why he believes the only way you fail as a founder is if you stop.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters

(00:00) - Intro

(01:47) - The airlock between users and AI

(07:45) - Why AI safety resonates with Stephen personally

(09:30) - Big wins this year

(11:50) - Be a river, find a way around the obstacle

(13:32) - Helping app developers see they don't have safety covered

(19:49) - Evolving as a leader

(24:10) - Thinking forward, not just executing in the present

(26:41) - Investing in leadership

(28:12) - The intros Stephen is looking for

(31:30) - Closing thoughts

Links & Resources

• Stephen’s LinkedIn: https://www.linkedin.com/in/steve-calhoun/
• Guest Website: techviz.us

Keywords

founders, entrepreneurship, AI safety, AI middleware, SASI, Technical Visionaries, Stephen Calhoun, AI chatbot safety, AI for kids, EdTech AI, mental health AI, AI governance, AI insurance, AI compliance, Seldonian principle, deterministic AI, AI airlock, McAfee for AI, multi-time founder, founder resilience, ownership culture, leadership

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

This week, Josh sits down with Jenny Duan and Abhinav Agarwal, co-founders of Clair Health, the company building the world's first continuous hormone monitor for women. Think Oura or Whoop, but for hormones. Within ten weeks of launching, they had 25,000 women on the waitlist and 3,000 pre-orders. Their first batch sold out in weeks. Jenny and Abhinav open up about saying no to a "no" from a top accelerator, why women's health has been chronically underserved by medicine, and the transition every early founder eventually faces — from quarterback to coach.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters 

(00:00) - Intro & meet Jenny and Abhinav

(01:46) - What Clair Health does: the CGM moment for hormones

(06:15) - Why this resonates personally for Jenny and Abhinav

(10:57) - Big wins

(15:01) - Rejected by an accelerator and rejecting the rejection

(17:46) - Closed mouths rarely get fed

(17:54) - Racing against time on a hardware launch

(18:56) - Evolving as leaders: from quarterback to coach

(22:52) - The next growth step

(25:21) - How Jenny and Abhinav are investing in their own leadership

(28:43) - Closing thoughts

Links & Resources 

• Jenny’s LinkedIn: https://www.linkedin.com/in/jennysduan
• Abhinav’s LinkedIn: https://www.linkedin.com/in/agarwalaabhinav/
• Clair Website: wearclair.com

Keywords 

founders, entrepreneurship, women's health, FemTech, hormones, continuous hormone monitor, wearables, perimenopause, menopause, PCOS, endometriosis, CGM moment, Clair Health, Jenny Duan, Abhinav Agarwal, co-founder dynamics, hardware startups, Speedrun accelerator, fundraising, female longevity, hormone tracking, women in healthcare 

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

This week, Josh sits down with Ali Ahmed, CEO and co-founder of RoboMart — the company building self-driving stores and autonomous delivery robots that are 70-80% cheaper than any delivery option out there. RoboMart is Ali's 5th startup. Four of his previous ventures didn't make it. He opens up about why he keeps building, why founders need a little naivety to survive, and why robotics is the hardest startup category in the world.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters

(00:00) - Intro

(01:33) - The problem RoboMart solves

(04:00) - Self-driving stores, the RM5, and what makes the model work

(10:07) - Launching the RM5 and the autonomous driving stats behind it

(11:42) - 5 startups, 4 failures, and why patience matters

(15:32) - The .333 batting average 

(19:45) - Biggest challenge

(21:38) - How Ali has evolved as a leader

(23:55) - The next evolution: from builder to platform operator

(29:39) - Closing Thoughts

Links & Resources 

• Ali Ahmed LinkedIn: https://www.crunchbase.com/person/ali-ahmed-2
• Robomart: https://robomart.ai/
  

Keywords

founders, entrepreneurship, robotics startups, autonomous delivery, self-driving stores, RoboMart, Ali Ahmed, on-demand delivery, last-mile logistics, hardware startups, robotics manufacturing, series A, founder resilience, multiple startups, ownership culture, retail innovation, autonomous vehicles, RM5, full self-driving, founder lifestyle

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

This week, Josh sits down with Chelsie Hall, founder and CEO of Viral Moment — the AI platform that watches social video at scale so brands like Coca-Cola, Warner Brothers, and Mattel can understand what's actually happening across culture in real time. Chelsie opens up about the spreadsheet of 100+ VC calls that built her fundraising playbook, the ego death of realizing what she wanted to build wasn't quite what the market wanted, and what it's been like building a company while becoming a mom to two littles.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters 

(00:00) - Intro

(02:01) - What Viral Moment actually does

(07:45) - Why this resonates with Chelsie

(10:39) - Wins in 2026

(12:03) - 100 VC calls and the ego death of mission vs. market

(17:47) - A shifting AI market

(21:11) - Evolving as a leader

(25:02) - How Chelsie invests in herself

(27:16) - Who ViralMoment works with

(28:00) - Closing thoughts

Links & Resources 

• Chelsie LinkedIn: https://www.linkedin.com/in/chelsie-hall
• ViralMoment: https://viralmoment.com/
• The Gap and the Gain by Dan Sullivan & Benjamin Hardy: https://gapandgainbook.com/

Keywords

founders, entrepreneurship, AI for marketing, social video AI, video analytics, consumer insights, brand intelligence, Viral Moment, Chelsie Hall, hate speech detection, disinformation, culture mapping, mom founders, fundraising rejection, 100 VC calls, mission-driven business, market fit, AI adoption curve, enterprise sales, Techstars, The Gap and the Gain, psychotically present, founder burnout, work-life integration 

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

This week, Josh sits down with Jonathan Festejo, CEO of SalesBricks — the platform unifying pricing, contracts, e-signing, and payments into one B2B sales motion. Jonathan opens up about the new-dad quarter-end moment that pushed him to start the company, the absurd contract failures his team has seen in the wild (yes, including divorce papers accidentally merged into MSAs), and why "time kills all deals" is the principle reshaping how he thinks about every interaction.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters

(00:00) - Intro

(01:44) - Meet Jonathan Festejo & SalesBricks

(05:55) - Why this problem?

(12:20) - Big wins this year: investing in the buyer experience

(16:40) - Wisdom is failure redeemed 

(18:25) - The hard-earned lesson

(20:33) - Focusing on the right ICP

(26:09) - Evolving as a leader

(28:03) - Ownership culture: alignment, accountability, autonomy

(34:30) - Closing thoughts

Links & Resources

• Jonathan’s LinkedIn: https://www.linkedin.com/in/jonathan-festejo-a52565256
• Salesbricks: https://www.salesbricks.com

  
  

Keywords 

founders, entrepreneurship, B2B SaaS, revenue operations, rev ops, sales infrastructure, quote-to-cash, pricing and packaging, usage-based billing, performance billing, contract management, DocuSign alternative, SalesBricks, buyer experience, seller experience, B2B buying, delegation, ownership culture, founder hiring, ideal customer profile, ICP, time kills all deals, Jonathan Festejo

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

This week, Josh sits down with Eric McHugh, president and co-founder of Dating — the first AI-powered matchmaking platform that auto-generates dating profiles from your digital footprint and uses an LLM called Cupid as a "relationship butler." Eric opens up about the structural problem with every other dating app, the bot-army shakedown that taught him to say no to bad investors, and why in the age of vibe-coding, trust is the only moat that lasts.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters

(00:00) - Intro

(01:12) - Meet Eric McHugh & Data-ing

(02:18) - How Dating works: digital footprints, tags, and Cupid AI

(09:31) - Why this problem

(11:24) - When Cupid AI saved a real relationship

(17:31) - The social commerce startup and the "Instagram bot army" shakedown

(19:57) - Matching people to who they're truly compatible with

(21:49) - Evolving as a Leader

(28:21) - Advice for founders

Links & Resources 

• Eric McHugh: https://www.linkedin.com/in/ericdouglasmchugh
• Data-ing Website: https://dataing.io/
  

Keywords 

founders, entrepreneurship, AI matchmaking, dating apps, Tinder alternatives, relationship technology, Cupid AI, AI-powered apps, digital footprint, bootstrapping, self-funded startups, bad investors, founder lessons, vibe coding, AI trust, ownership culture, alignment accountability autonomy, spiritual entrepreneurship, conscious creation, Eric McHugh, Dating app, startup community building

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

This week, Josh sits down with Harjiv Singh, founder of CambrianEdge.ai, the world's first AI-native, human-led marketing platform. After 25 years in marketing and a 2001 startup story that ended with their investors' building destroyed in the September 11 attacks, Harjiv shares what it actually takes to come back, build again, and lead through a technological shift the size of electricity itself. 

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters 

(00:00) - Intro

(01:07) - Meet Harjiv Singh & CambrianEdge.ai

(06:40) - The product team and the beta feedback

(08:35) - The fear of AI and the case for AI literacy

(10:39) - Building the world's first app before the word "app" existed

(13:03) - April 2001 to September 2001: when everything went wrong

(17:47) - Why every tech shift creates more jobs than it kills

(19:59) - Evolving as a leader

(24:54) - Closing thoughts

Links & Resources

• Harjiv’s LinkedIn: https://www.linkedin.com/in/harjivsingh
• Company Website: cambrianedge.ai
  

Keywords

founders, entrepreneurship, AI marketing, marketing technology, martech, AI-native platforms, AI literacy, AI fluency, enterprise marketing, B2B marketing, performance marketing, marketing analytics, generative AI, AI evangelism, startup resilience, dot-com bust, 9/11 startup story, World Trade Center, technological shifts, candle to electricity, Isaac Newton, leadership in AI, founder lessons, Harjiv Singh, CambrianEdge

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

In this insightful interview, Jonathan Hunt-Glassman, CEO of Oar Health, shares his journey in building a digital health company focused on helping individuals reduce or quit alcohol use. The discussion covers the challenges of medication supply chains, the importance of adaptive leadership during crises, and innovative approaches to expanding access to evidence-based treatments.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters

(00:00) - Introduction

(03:43) - Understanding Alcohol Use Disorder  

(09:20) - Coaching and Support in Recovery  

(11:53) - Lessons Learned from Challenges  

(18:30) - Adapting to Market Changes  

(24:35) - Evolving as a Leader  

(28:16) - Investing in Personal Development  

(31:05) - Building Partnerships for Better Care  

Links & Resources

• Jonathan’s LinkedIn: https://www.linkedin.com/in/jhuntglassman
• Oar Health Website: https://www.oarhealth.com/
• Ron Heifetz, The Practice of Adaptive Leadership: https://www.amazon.com/Practice-Adaptive-Leadership-Changing-Organization/dp/1422105768
• HBR, The Work of Leadership: https://hbr.org/2001/12/the-work-of-leadership

Keywords 

alcohol use disorder, medication-assisted treatment, telehealth, adaptive leadership, supply chain resilience, behavioral health, addiction recovery, healthcare innovation

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

Anita Balaraman, founder and CEO of Epixego, shares her journey from accidental educator to innovator in career development. Discover how her competency fingerprint technology bridges awareness gaps in education and workforce development, and learn about her insights on scaling impact and leadership in a complex environment.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters

(00:00) - Introduction to Founder Real Talk  

(02:26) - Anita's Journey to Founding Apixigo  

(10:13) - Current Status and Wins of Apixigo  

(13:43) - Lessons Learned from Entrepreneurship  

(19:54) - Challenges and Future Growth of Apixigo  

(24:50) - Investing in Leadership Growth  

(29:08) - Scaling Challenges and Workforce Development  

Links & Resources

• Anita’s LinkedIn: https://www.linkedin.com/in/anita-balaraman-10a4211
• Epixego: https://epixego.com/
  

Keywords 

career development, education technology, competency fingerprint, workforce development, startup scaling, social capital, mentorship, higher education innovation

Welcome to Founder Real Talk, a podcast for founders, by founders. 

We explore the real journey of building and growing a company. Each episode, we go beyond the highlight reel to unpack the strategies, decisions, and hard lessons that shaped successful businesses, revealing the good, the bad, and the ugly behind the growth.

In this insightful interview, Andrew Mao shares his journey of building Parsnip, an AI-powered learning platform for cooking and life skills. He discusses the challenges of startup life, the impact of AI on education, and the importance of emotional intelligence and leadership development.

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This episode was brought to you by Wisdom Partners. If you’re looking for more real conversations, practical resources, and honest founder stories, follow us for upcoming episodes of Founder Real Talk. We invite you to subscribe to our Substack newsletters to receive weekly articles, insights, and resources designed to support founders through every stage of the journey!

Contact us: wisdompartners.llc/contact

Subscribe to our Substack: blog.wisdompartners.llc

Chapters 

(00:00) - Introduction to Founder Real Talk  

(02:10) - The Journey of Parsnip.ai  

(04:28) - The Challenge of Learning to Cook  

(07:37) - Wins and Challenges in the Past Year  

(11:39) - The Future of Education and AI  

(14:38) - Lessons Learned the Hard Way  

(18:08) - Investing in Leadership and Emotional Intelligence  

(21:07) - Current Challenges and Business Model Exploration  

(22:18) - AI Coaching: Expanding Horizons  

(26:43) - Building Organizational Culture: The Dual Product  

Links & Resources

• Andrew’s LinkedIn: https://www.linkedin.com/in/mizzao
• Parsnip AI: https://www.parsnip.ai/team

Keywords 

AI education, startup journey, leadership, emotional intelligence, personalized learning, cooking, knowledge mapping, founder challenges