The Dear Tech Podcast

A Craigslist ad paid his college tuition. A bad billing structure almost killed his company. Now he’s building a product because he believes SaaS, as we know it, is done. Hunter Jensen breaks down what actually happens between your first client and real scale, and why generative AI is forcing service businesses to rethink everything from pricing to product strategy. Episode summary Hunter Jensen s...

In this episode, we sit down with Dennis "DM" Meador, a marketing strategist who helps professional business owners and service providers build market authority. DM opens up about his background, growing up in difficult socioeconomic circumstances and how those early experiences shaped his entrepreneurial mindset. The conversation explores his evolution from early entrepreneurial activities to his...

In this episode, I sit down with Ivan Vislavskiy, co-founder and CEO of Comrade. Ivan built his agency from the freelance web projects he started at 19 into a national digital firm with nearly 100 team members across four major cities. What stood out in this conversation is how grounded his view of AI is. AI will not replace real marketing. It makes basic output cheap, which means the work that st...

🎧 One-Sentence Summary Raj Singh, Vice President at Mozilla and builder of Solo, joins Shubho to explore how AI is transforming web creation, empowering solopreneurs, and redefining the future of small business tools. Full Episode Summary In this episode of The Dear Tech Podcast, Shubho sits down with Raj Singh, a serial entrepreneur and product leader at Mozilla, to talk about the massive shift...

Episode Summary Balki Kodarapu has turned engineering disasters into scaling success stories across five startups that raised over $160 million with one successful exit. As a fractional CTO, he's mastered the art of walking into chaos and creating systems that make developers actually happy while hitting impossible deadlines. In this conversation, we explore his unique philosophy of carving out 15...

Harrie Bickle, technical writer and documentation lead at NodeOps, explains why Web3's promise hasn't faded, it's just being built while the world looks away, and how decentralized infrastructure is quietly becoming inevitable. Episode Summary In this episode, Shubho sits down with Harrie Bickle, a technical writer who's spent years translating complex Web3 technology for everyday users. Harrie sh...

Discover how a rebellious factory worker earning $2/day transformed into an AI pioneer generating $500M+ in client value—and his blueprint for merging human consciousness with artificial intelligence. Episode Summary Manuj Aggarwal's journey from earning $2 a day in his father's Indian factory to building a bootstrapped tech consultancy worth hundreds of millions is just the beginning. In this tra...

Grant McCracken, founder and CEO of DarkHorse Security, joins us to discuss how he's revolutionizing cybersecurity by making proactive security easier to use and more accessible for businesses of all sizes. From backpacking around the world for a year to living in a travel trailer during COVID exploring national parks, Grant's unconventional journey has shaped his approach to disrupting the tradit...

Burnout is not a personal flaw, it is a signal. In this episode, Work-Life Balance and Harmony Coach (and AV-rated Colorado attorney) Arlene Cohen Miller explains how burnout shows up in different forms, why “balance” is a moving target, and how simple reframes plus tiny daily rituals can pull you back to center. We talk breath work you can do while someone’s ranting at you, gratitude practices th...

My guest today is Tim O’Hearn , author of Framed: A Villain’s Perspective on Social Media —a #1 Amazon Bestseller that breaks down how our feeds, notifications, and recommendations are engineered to manipulate us. But Tim isn’t just an author. He’s spent 8+ years as a software engineer in quant finance, made over $500,000 through social media growth hacking , and literally built the systems that s...

What if your financial advisor had no ego, no sales pitch, and no fear of a market crash? Just data, logic, and objective guidance designed around your life? In this episode, Shubho sits down with Alexander Harmsen , CEO of PortfolioPilot.com , a personal AI financial advisor that’s helping over 30,000 users manage $30B+ in assets—and quietly revolutionizing how everyday investors make decisions....

What happens when a former JP Morgan exec leaves Wall Street to solve one of cannabis tech’s hardest problems? In this episode, I talk to Aubrey Amatelli , Founder and CEO of PayRio , the first payment provider exclusively built for cannabis, CBD, and alternative medicine. Aubrey bootstrapped PayRio to profitability in under a year, built a 100% women-led leadership team, and was recently named th...

Bryan Clayton went from pushing a lawn mower at 13 to building and selling a multimillion dollar landscaping company. Then he taught himself to code and built his next venture from scratch. In this episode, he joins The Dear Tech Podcast to share what it really takes to build a national tech platform without outside funding, formal training, or Silicon Valley connections. We talk about the power o...

Warren Wilansky has been building for the web since the ‘90s, but what makes his story stand out isn’t just longevity—it’s intention. As the Founder and President of Plank , a B Corp Certified digital agency, Warren has spent the last 25 years helping mission-driven organizations create ethical, inclusive, and accessible digital platforms that actually serve their communities. In this episode, we...

In this eye-opening episode, we sit down with Dr. Elliot Justin , a Harvard-trained physician, ER veteran, and founder of FirmTech — the company behind the Tech Ring , a groundbreaking wearable that turns your erection into a vital health signal. We talk about why erectile dysfunction is misunderstood, how erections are linked to cardiovascular health, and what 70,000+ data points are revealing ab...

Show Notes: Too many companies launch with the belief that a great product will naturally attract customers. The truth? Without the right messaging and strategy, even the strongest ideas struggle to gain traction. In this episode, Shubho sits down with Angelo Ponzi, a seasoned brand strategist and fractional CMO, to unpack what actually drives marketing success in early-stage and growth-stage busi...

What does true innovation in healthcare look like beyond the buzzwords? In this episode, we sit down with Richard “RJ” Kedziora, Co-Founder of Estenda Solutions, to talk about the real state of digital health today—from AI-driven ambient listening tools to remote patient monitoring and EMR frustrations. RJ brings decades of experience designing and implementing data-powered healthcare tools. He sh...

In this episode of Dear Tech , we sit down with Lori Crooks, Founder and CEO of Cadra, a cybersecurity consultancy on a mission to make compliance approachable for businesses of all sizes. Lori brings over 20 years of experience in IT auditing, security frameworks, and technical documentation — but her journey didn’t start in tech. We dive into her path from finance to IT auditing, what inspired h...

Dan Hafner never set out to be an entrepreneur, but his winding path through teaching aspirations, software QA, and remote work led him to create  Dapper No-Code  — a company that helps founders build and launch software without writing code. In this episode, we explore how Dan turned a personal fitness app idea into a full-fledged business, what most people get wrong about no-code, and...

We’re back, and we’re doing something special. In this episode, we’re looking back at the moments that defined Season One of Dear Tech . This isn’t just a highlight reel — it’s a celebration of the honesty, the vulnerability, and the power of real talk in a tech world that often forgets the human behind the resume. From navigating job searches and negotiating comp, to burnout, layoffs, pivots, and...

Episode Summary: In this episode of  Dear Tech , Shubho sits down with Taylor, co-founder of Ambient, to explore his journey through startups, AI, and the importance of mental fitness. Taylor shares insights from his experiences in event tech, pivoting businesses in the face of adversity, and how his passion for sailing has shaped his leadership approach. Whether you're a startup founder, a t...

Fran and Shubho speak with Tahmid about is journey from dead end job all the way to leading a team in a IT environment. They start with Tahmid's weight loss which was the spring board to him changing his life and taking on new challenges, the biggest of which was Technology.

Fran and Shubho have an in depth conversation with Dev about his journey from student in India to Product Manager in the United States. They discuss the navigating the transition of going to school in the US after studying in India and then securing an internship; and from internship to securing a full-time job.

00:00 - Intro 00:20 - Kicking off - how do Sanjit and Shubho know each other 05:16 - the love of tech is generational 8:35 - Sanjit is not a coder 11:42 - what Sanjit does today 12:58 - What got Sanjit to where he is today (motivation & Path) 17:42 - Working at a start up vs working at a large enterprise 20:28 - Motivations going into the MBA program 23:31 - Coming from tech, who would you rec...

Elle Anderson Joins our host Fran & Shubho to give the perspective of Human Resources on the Great Resignation in tech and the current market and the changes since then. The Great resignation being the topic of Elle's Masters thesis we are able to get an in depth perspective of what was happening at that time; getting perspectives of both HR and the exiting employees.