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 summaryHunter Jensen started exactly where a lot of founders do, taking on freelance work while still in school. One Craigslist post landed his first real client, an ecommerce business that not only paid his tuition but gave him the proof he needed to keep compounding work.From there, Hunter shares how he shifted his mindset from solo freelancer to building a real agency, including why he intentionally did early projects cheap or free to plant a flag in new markets. He also walks through the least glamorous but most important lesson he learned, cash flow. A six figure project dragged on for months waiting for acceptance, nearly putting him out of business and forcing a permanent change in how he billed clients.The conversation then turns to generative AI. Hunter explains why selling engineering hours is getting squeezed, why “business as usual” is risky, and how that pressure led to Compass, a self hosted internal AI platform for companies that cannot use public tools due to security and confidentiality concerns. He also shares how AI adoption really happens inside organizations and why the next wave of successful startups will be built on proprietary data, not first mover advantage.You’ll learnHow Hunter used early low cost projects as a wedge to break into bigger marketsThe billing model change that protected his business from cash flow collapseWhy in person meetings still build trust faster, even in a remote worldHow internal AI adoption spreads through champions, not top down mandatesWhy Hunter believes SaaS is dead and proprietary data is the real moatGuestHunter JensenFounder and CEO at Barefoot LabsBuilt and scaled a services agency for 20 plus yearsCreator of Compass, a product plus services internal AI platform for confidential workFind HunterWebsite: barefootlabs.aiEmail: [email protected] your email with: “I heard you on the Dear Tech Podcast”He said he’ll personally replyResources and mentionsNever Split the Difference by Chris VossCompass by Barefoot Labs, self hosted internal AI platformbarefootlabs.aisiptequila.com,...

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 work in the legal space, including his experience with the Legal Podcast Network. DM discusses how his "island living" philosophy and geographic positioning influence his approach to business and working with professional clients.His story offers a fresh perspective on how location, lifestyle choices, and unconventional thinking can inform business strategy, showing how personal experiences and geographic awareness can create unique opportunities in professional service markets.Guest BioDennis "DM" Meador is a marketing strategist who helps professional business owners and service providers like attorneys, doctors, consultants, and firm owners position themselves with authority in their markets. With 30 years of business and marketing experience and two decades focused on the legal and white-collar space, he specializes in helping professionals build lasting authority through podcasting, content, and strategic positioning.Key TopicsLegal Industry Experience: Background with Legal Podcast Network and legal space expertiseEarly Entrepreneurship: Starting business activities at a young age despite difficult circumstancesIsland Living Philosophy: How geographic location and lifestyle choices influence business approachSocioeconomic Background: How challenging early circumstances can fuel entrepreneurial driveProfessional Services: Working with business owners and service providersUnconventional Strategies: Using non-traditional approaches to identify opportunitiesTop TakeawaysGeographic location and lifestyle can inform business philosophyChallenging backgrounds often fuel innovative business approachesLegal industry experience provides deep market understandingEarly entrepreneurial experiences shape long-term business thinkingIsland living offers unique perspectives on professional positioningUnconventional approaches can reveal overlooked market opportunitiesAbout the ShowThe Dear Tech Podcast explores entrepreneurship, technology, and business innovation through conversations with founders, researchers, and industry leaders. Host Shubho brings nearly a decade of tech recruiting experience to uncover the stories behind successful ventures and emerging trends.Calls to ActionIf you enjoyed this conversation with DM about entrepreneurship and professional services, please share it with fellow entrepreneurs and business owners. Rate the show on your favorite podcast platform and subscribe to never miss an episode of Dear Tech Podcast.

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 stands out takes more judgment, more strategy, and more creative thinking than the average person expects.We get into how his R&D and Innovation team uses AI to automate thousands of hours, how he thinks about measuring real impact, and why he still trusts human intuition over anything a model produces. Ivan breaks down the difference between speed and leverage, how agencies should define a niche, and why thinking like a founder is becoming the skill that separates high performers from everyone else. We also talk about parenting, critical thinking, and a fun moment where Ivan explains how he uses AI to create custom coloring pages for his kids.If you want a grounded, practical view of where AI is taking marketing and creative work, this episode delivers it in a way that actually makes sense.About Ivan VislavskiyIvan Vislavskiy is the co-founder and CEO of Comrade Agency, a full-service digital firm with offices in Chicago, Miami, Los Angeles, and Austin. With a background as a developer and designer, Ivan brings a rare mix of creative intuition and technical depth. He leads an internal R and D and Innovation group focused on using AI to automate repetitive work and unlock higher level creative output for both clients and his team.Key TopicsWhy AI raises the bar for great marketingThe difference between speed and leverage in creative workHow Comrade measures AI’s true impactWhy creativity and intuition still matterBuilding and committing to a clear nicheHow to teach teams to use AI without outsourcing their thinkingParenting and staying curious in the age of AIWhat agencies get wrong about AIThe next five years of AI in digital marketing and creative workTop TakeawaysAI makes basic marketing fast and cheap, which means real creativity becomes more valuable.Strategy and judgment are the new competitive advantage.Teams that treat AI as a thinking partner outperform teams that use it for shortcuts.Agencies that define a niche grow faster and build stronger client relationships.Human intuition is still the final filter for all high quality creative decisions.Memorable Quotes“AI doesn’t lower the bar for great work. It raises it.”“Speed is useful, but speed without judgment creates noise.”“You can not outsource intuition to a model.”“Niche down or stay invisible.”“Creativity is the thing that survives every wave of technology.”Resources MentionedComrade AgencyExamples of their internal R&D automationsWorking Backwards: Insights, Stories, and Secrets from Inside Amazon Hardcover- by Colin Bryar, Bill Carr Where to Find Ivan:LinkedIn: linkedin.com/in/ivan-vislavskiyComrade Agency: comradeweb.comAbout Dear Tech PodcastDear Tech Podcast is hosted by Shubho Ghosh and dives deep into the human stories, strategy, and real world insights behind the-people building the future of work, technology, and AI.

🎧 One-Sentence SummaryRaj 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 SummaryIn 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 happening in the digital economy. Raj shares the story behind Solo (https://soloist.ai/), Mozilla’s new AI-powered website builder designed for solopreneurs and freelancers who want to build a brand without technical hurdles.They unpack how consumer behavior toward paying for software is changing, what makes today’s solopreneurs different, and how AI is enabling “super individual contributors” who can do the work of entire teams.Raj also opens up about his unconventional founder journey—from building file-sharing networks in college to multiple successful exits—and what he’s learned about innovation, focus, and the mindset needed to build and rebuild from scratch.Guest BioRaj Singh is a serial entrepreneur and product leader currently serving as Vice President at Mozilla, where he leads new product initiatives focused on small business tools, including Solo, an AI-driven website builder for solopreneurs. With multiple successful exits, Raj has spent over two decades building consumer products and zero-to-one startups at the intersection of design, AI, and web technology.Linkedin: https://linkedin.com/in/rajansinghX: https://x.com/mobilerajKey TopicsAI and Solopreneurs: Why generative AI is powering a new wave of one-person businessesBuilding Solo: The inspiration behind Mozilla’s AI website builder and what makes it differentConsumer Behavior: How users are now willing to pay for AI tools that feel valuableThe Super IC: Raj’s idea of the “super individual contributor” and what it means for the workforceAI Tourism: The explosion of short-term tool experimentation in tech companiesUpskilling Mindset: Practical ways to adopt AI in your daily workflowFounder Psychology: The emotional arc after an acquisition—from relief to acceptanceZero-to-One Thinking: How to evaluate product ideas and find founder-product fitMozilla’s Mission: How Solo fits into Mozilla’s broader vision for an open, accessible webFuture of Small Business Tools: Automating back-office work so creators can focus on what they loveTop TakeawaysGreat AI tools don’t just automate tasks, they free people to focus on high-leverage workUpskilling with AI isn’t optional anymore—those who use it effectively will outpace those who don’tThe next big wave of innovation will come from solopreneurs, not corporationsConsumer willingness to pay is growing, but only when tools save real time or reduce frictionPersonal pain points make the best startup ideas—build what frustrates you mostNever design to get acquired; design to build something real and valuableThe best time to start is now—there’s no perfect timing for entrepreneurshipMemorable Quotes“Your margin is my opportunity.” — Raj“AI isn’t replacing people, it’s replacing low-leverage work.” — Raj“You won’t be replaced by AI, you’ll be replaced by someone who uses AI.” — Raj“If the passion is there, it’s not going away. The best time to...

Episode SummaryBalki 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 hours per week for learning and growth, his four pillars of engineering excellence, and how he built trust by buying his team lunch with coupons. From mechanical engineering dropout to startup whisperer, Balki shares practical frameworks for developer effectiveness, the real cost of over-hiring, and why the best thing an engineer can do is sit quietly and not write code.Guest BioBalki Kodarapu is a fractional CTO with over 20 years in the industry who has worked with five startups that collectively raised over $160 million, including one successful exit. He specializes in scaling engineering teams and has developed frameworks for engineering excellence, developer effectiveness, and building high-performing technical organizations.Key TopicsDeveloper Happiness: Why investing 15 hours per week in learning, reflection, and growth pays dividendsFractional Leadership: The advantages and trade-offs of fractional CTO roles versus full-time positionsEngineering Excellence: Four core pillars including observability, automation, CI/CD, and modular architectureChaos Management: How 90% of software engineering chaos is predictable and manageableTeam Building: Creative recognition strategies and the importance of making developers feel heardHiring Strategy: When to slow down hiring and the expensive mistakes of over-staffingAI Impact: Four ways generative AI is transforming software organizations beyond just codingWork-Life Balance: Personal philosophy on intentional focus and the role of community networksCost Optimization: Common expensive oversights like cloud spend and unnecessary tool proliferationChapter Markers00:00 Introduction and the 15-hour learning philosophy04:11 Career journey from mechanical engineering to fractional CTO12:11 First leadership role and creative team recognition18:00 Developing a knack for managing chaos26:00 Fractional vs full-time CTO differences34:41 Hiring challenges and building trust42:00 Developer effectiveness and engineering excellence framework54:17 Work-life balance and personal philosophy59:29 AI's impact on engineering and 10-year predictions62:24 FAQs and personal insightsTop TakeawaysCarve out 15 hours per week for learning and growth - it's more critical now with AI changing everything90% of engineering chaos follows predictable patterns: quality, observability, deployment, and modular issuesThe four pillars of engineering excellence: observability, test automation, CI/CD, and modular architectureCreative recognition matters more than expensive perks - buying lunch with coupons built stronger relationshipsDon't hire irresponsibly just because you have VC money - clean your house firstDeveloper effectiveness means engineers can commit code on day one and see it in production within their first cycleBuild trusted peer networks and contribute 51% while extracting 49% valueThe best advice for engineers: sit quietly and don't write code unless you really need toResources & MentionsBooks:Audacity to Start by Balki's children - A book about starting a...

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 SummaryIn this episode, Shubho sits down with Harrie Bickle, a technical writer who's spent years translating complex Web3 technology for everyday users. Harrie shares her unconventional path from biology and teaching to becoming a documentation specialist in the blockchain space, working with companies like StarkWare and now NodeOps. The conversation explores why Web3 hype died down after 2021, what's actually being built behind the scenes, and how NodeOps is making decentralized cloud computing accessible to non-technical users. Harrie breaks down the difference between being "there for the computer" versus "there for the casino" in crypto, explains NodeOps' innovative DePIN 2.0 tokenomics model, and discusses why regulatory battles, not technical limitations, are the real challenge facing blockchain adoption. They also tackle the hidden costs of data collection, the tension between anonymity and regulation, and why Bitcoin miners might become the backbone of tomorrow's cloud infrastructure.Guest BioHarrie Bickle is a technical writer and documentation lead at NodeOps, a decentralized infrastructure network. She previously worked with StarkWare and Infura, bringing nearly two decades of experience translating complex technology for diverse audiences. Before entering Web3, Harrie taught in Cape Town and built a freelance technical writing practice on Upwork, eventually specializing in blockchain documentation.Key TopicsWeb3 Documentation: Why clear technical writing is essential for bridging the gap between blockchain developers and everyday usersCareer Pivots: Harrie's journey from biology to teaching to technical writing, and how remote work platforms like Upwork enabled her transitionNodeOps Platform: How the company is democratizing access to blockchain nodes and decentralized cloud computing through simple app-based interfacesDePIN 2.0 Tokenomics: A dynamic mint-and-burn model that ties token emissions to actual demand and USD value, preventing over-inflationWeb3's Narrative Shift: Why media attention moved from blockchain to AI in 2021-2022, and what's still being built during the "quiet phase"The Computer vs. The Casino: Two fundamentally different motivations for participating in crypto, speculation versus solving real infrastructure problemsRegulatory Challenges: How companies like Google are restricting non-custodial wallets, and why regulation poses a bigger threat than technical barriersPrivacy Paradox: The tension between Web3's promise of anonymity and the reality of custodial wallets and KYC requirementsFuture of Cloud Computing: How unused hyperscaler capacity and Bitcoin mining operations could feed into decentralized compute marketplacesAvoiding Burnout: The importance of physical exercise and stepping away from the desk when working in fast-moving startup environmentsTop TakeawaysGood documentation is marketing: If users can't understand your product, they won't use it. This is especially critical in Web3 where technical barriers are high.Web3 hasn't failed, it's building: The drop in media hype doesn't mean blockchain technology stopped progressing; serious infrastructure work continued while attention shifted to AI.You're either there for the computer or the casino: Crypto attracts two types...

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 SummaryManuj 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 transformative conversation, he reveals his groundbreaking "AI Merge" framework—a peer-reviewed methodology that doesn't just make you more productive with AI, but creates a digital twin of your subconscious mind. This isn't about automating tasks; it's about unlocking the 90% of human potential most people never access.Key Takeaways• Think AI-First, Not AI-Second: Stop adding AI to existing processes. Instead, reimagine everything from an AI perspective and fill in the 20% that requires human input.• The Digital Twin Revolution: True AI adoption means merging your subconscious mind with artificial intelligence by feeding it your life experiences, creating an emotionally intelligent digital version of yourself.• Hiring Will Never Be the Same: Replace traditional interviews with storytelling—have candidates and managers share their backstories, then use AI to find perfect human-value alignment.• Universal High Income is Coming: As AI increases productivity 100x-1000x, we're heading toward universal high income (not basic income) where work becomes a choice and everyone becomes a fractional entrepreneur.• The Five Pillars of AI Merge: Purpose, Identity, Relationships, Creativity/Courage, and Time—a framework that can shift your identity and results within 2-4 weeks.• Pain is Your Teacher: Embrace setbacks as lessons rather than running from them. Each down teaches you something essential for the journey ahead.Episode Outline / Timestamps01:31 - From Factory Floor to Tech Pioneer: The $2/day origin story08:37 - First encounter with computers and falling in love with technology10:46 - Immigration to Canada and the dot-com boom/bust experience18:16 - The birth of Tetra Noodle and scrappy entrepreneurial tactics22:16 - The wild "All Advantage" internet hustle with PO boxes27:07 - Evolution from solo consultant to team leader33:35 - Introduction to the AI Adoption Blueprint and AI Merge framework37:32 - Creating digital twins that tap into your subconscious mind48:02 - Real-world success stories: executives doubling salaries, day traders improving performance50:31 - Revolutionary hiring process using storytelling and AI matching1:00:07 - The future of work: from employees to fractional entrepreneurs1:04:31 - Common AI adoption mistakes and thinking "AI-first"1:16:28 - Overlooked sectors ripe for AI disruption: energy and creative arts1:19:17 - Meditation myths and making self-development fun1:22:53 - What's next: working on moonshots and Nobel Prize-worthy projectsGuest IntroductionManuj Aggarwal - Founder & CEO of Tetra NoodleBootstrapped tech consultant who has generated over $500 million in client value, helped 10+ million people, and holds multiple patents. Creator of the peer-reviewed "AI Merge" framework published in Mentha Research Journal. Known for his revolutionary approach to AI adoption that focuses on human consciousness rather than just productivity tools.Connect with...

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 traditional pen testing industry. Now based in the mountains where he enjoys trail running and skiing, Grant brings over 13 years of cybersecurity experience as both an ethical hacker and former VP of Operations at Bugcrowd to building something completely different.Guest BioGrant McCracken is the founder and CEO of DarkHorse Security, an innovative startup that's making proactive cybersecurity easier to use and more accessible for businesses of all sizes. With over 13 years in cybersecurity, Grant has experience both as an ethical hacker and as an executive at Bugcrowd, where he served as VP of Operations, overseeing all aspects of service delivery. When he's not building the future of accessible cybersecurity, Grant enjoys making and playing music, writing, reading, learning, breaking things, building things, hiking, trail running with his dog, and skiing when there's snow.Key Topics DiscussedThe DarkHorse Security RevolutionMaking penetration testing accessible with transparent pricing at darkhorse.shWhy traditional cybersecurity vendors overcomplicate everythingThe "breaches are expensive, Dark Horse isn't" philosophySetting up pen tests in 5-15 minutes instead of months of sales cyclesReal-time vulnerability tracking and methodology transparencyCybersecurity Landscape in 2025AI-powered deepfake attacks: the scariest emerging threat for small businessesWhy audio and video spoofing will accelerate human-layer breachesNew vulnerability categories introduced by AI (prompt injection, LLM poisoning)The staggering reality: 900+ organizations hit by ransomware in one weekThe Entrepreneurial JourneyFrom WhiteHat to Bugcrowd VP to solo founderWhy relationships trump cold outbound every timeThe unique confluence of skills needed to disrupt cybersecurityLearning sales, marketing, and business development on the flyWhy he chose independence over corporate securityLife Beyond the ScreenBackpacking through 30 countries and 100+ cities for a yearCOVID travel trailer life: exploring national parks while working remotelyMountain living philosophy: "one step at a time" applies to everythingHow trail running and skiing influence business decisionsWhy independence and agency drive all his life choicesResources & ConnectionsDarkHorse Security: https://darkhorse.shGrant's LinkedIn: https://www.linkedin.com/in/grantmccracken/Episode HighlightsThe reality of cybersecurity for cash-strapped startupsHow travel and adventure shaped an unconventional business philosophyWhy the security industry is ripe for disruptionPractical threat assessment for 2025The intersection of personal growth and professional successSubscribe for more conversations with founders who are redefining their industries, one step at a time. Share this episode with any startup founder who thinks good security has to break the bank.

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 that actually move the needle, spotting “energy leaks,” setting real boundaries, and building team cultures that don’t quietly chew people up. If you’ve been running on fumes or numb autopilot, this conversation gives you language, tools, and a first step.Learn more or book Arlene for workshops: JewelConsultancy.comKey TakeawaysBurnout is a spectrum: it starts with “I’m tired” and can slide into immobilization if ignored.Awareness first: notice your body’s signals, headaches, irritability, or staring blankly at a screen.Breath work is a portable reset: longer exhale than inhale through your nose can downshift your nervous system fast.Gratitude is practice, not luck: pick one thing, feel it fully for a second, let it expand your inner space.Boundaries are energetic and practical: cut cords daily, send back what is not yours, and say “not right now” when someone dumps on you.Mentorship matters: action cures fear, and mentors shortcut the lonely middle of “I don’t know what I’m doing.”Balance is not a fixed point: harmony or rhythm is a better target because life shifts every day.Rapid Fire HighlightsStress creeping in? Close the laptop, walk the block, breathe.Mood-lifting movie? When Harry Met Sally (that diner scene).Belief people get wrong about balance? That it’s ever perfect. Harmony is a better frame.Favorite recent read? Richard Bach’s Illusions.Best advice? “Any disaster can become a blessing, any blessing can become a disaster, and there is always a better way.”Resources MentionedJewel Consultancy: https://jewelconsultancy.comRichard Bach, Illusions (book reference)Pipedrive (CRM tool she is using to push herself out of her comfort zone)Connect with ArleneWebsite: JewelConsultancy.comLinkedIn: https://www.linkedin.com/in/arlenecohenmiller/Call to ActionIf you’re planning a conference, offsite, or internal workshop for a tech team and want a session on burnout, balance, or mindful productivity, reach out to Arlene. If this episode resonated, share it with a teammate who needs the reminder that they are not alone.Follow Dear Tech Podcast on Instagram @deartechpodcast and LinkedIn, and subscribe so you don’t miss the next deep-dive.

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 shape what you see online.In this episode, we dig into:How Tim reverse-engineered platforms to gain followers and viralityThe rise of bots, shadowbanning, and black hat marketingWhat it’s like to design feeds and push notifications from the insideWhy your attention is more valuable than your dataThe Dead Internet Theory and the eerie rise of AI-generated contentHow he transitioned from quant finance to gonzo tech criticWhether you’re a builder, marketer, or just curious about what’s really driving your social feed, this conversation will open your eyes.🔗 Connect with Tim O’Hearn:📘 Framed: A Villain’s Perspective on Social Media → Buy on Amazon🌐 Website → tjohearn.com💼 LinkedIn → linkedin.com/in/tohearn🧠 Topics Covered:[00:00] Intro: The Villain in the Feed[06:17] How Tim Made $500K in the Attention Economy[12:45] Reverse-Engineering Social Algorithms[19:32] Shadowbans and the Weaponization of Moderation[27:10] The Psychology of Notifications[35:22] The Dead Internet Theory and AI Content[42:55] From Quant Finance to Gonzo Tech Critic[49:30] Fixing Social Media: Can It Be Saved?[57:03] What Tim’s Reading Now[1:05:45] Final Thoughts and Where to Follow

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.We go deep into the psychology of money, how AI can help you stay rational when markets get volatile, and why financial tools need to feel more human to actually be effective.Alexander also shares the origin story of PortfolioPilot, what he learned scaling Iris Automation, his time building with NASA, and how he thinks AI will reshape the future of personal decision-making in everything from investing to health.What We Cover:Why Alexander originally built PortfolioPilot just for himself and why thousands now rely on itHow PortfolioPilot uses AI to eliminate financial bias and offer tailored, transparent recommendationsThe emotional traps people fall into with investing and how AI helps you navigate themReal stories of user psychology (including the guy with 40% of his net worth in Tesla)Lessons from building regulated AI systems (and why explainability matters more than hype)Startup wisdom: what Alex learned building Iris Automation and raising $30M+Why personalization, not general intelligence, is AI’s most underrated superpowerThe power and misunderstanding of tax-loss harvestingThe future of AI-powered financial tools (and why “gamification” isn’t always the right goal)🔥 Special Offer for Listeners:Try PortfolioPilot Gold FREE for 1 month→ Use promo code PODCAST at checkoutResources & Links:💼 PortfolioPilot.com🧠 Alexander on X/Twitter: @alexharm📺 PortfolioPilot on YouTube🧑‍💼 Alexander on LinkedIn📚 Books Mentioned:Spin Selling by Neil RackhamCrucial Conversations by Patterson, Grenny, McMillan & SwitzlerConnect with the Show:💬 Instagram: @deartechpodcast💼 LinkedIn: Dear Tech Podcast🌐 All links: linktr.ee/thedeartechpodcastIf you enjoyed the episode, please rate and review on Apple or Spotify—it helps more people discover the show! 🎙✨

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 the #1 Best Cannabis Company to Work For in 2025.We cover how she transitioned from banking to cannabis fintech, how she built trust in a high-risk industry, and why compliance and culture are two of her sharpest competitive advantages.You’ll also hear how she balances founder life with single motherhood, how her own mental health journey has shaped her leadership style, and what it really takes to build something sustainable without raising venture capital.🔍 We cover:Misconceptions about cannabis payments and legalityWhy compliance is a competitive advantage in fintechBootstrapping to profitability without outside investmentBuilding PayRio’s team through trust and culture-first hiringProcessing payments for cannabis, psychedelics, peptides, and moreHer role on NCIA’s Banking & Financial Services CommitteeLessons from JP Morgan that still guide her company todayBalancing motherhood and entrepreneurship under pressureThe power of showing up authentically in business📌 Links & ResourcesPayRio → https://www.payrio.coPayRio on Linkedin →https://www.linkedin.com/company/payrio/Instagram → @payrio_hqAubrey on LinkedIn → https://www.linkedin.com/in/aubreyamatelliIf you enjoy this episode, drop a review and share it with someone building in fintech, cannabis, or anywhere trust and grit are essential.

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 of discipline over motivation, what most non-technical founders get wrong, and how Bryan cold-called his way to a real user base. If you’ve ever thought, “I don’t have the background for this,” this episode might change your mind.🔍 Topics We Cover:The mindset shift from blue-collar business to tech founderTeaching yourself to code after building a $10M companyCold-calling 500+ vendors to build the first version of the platformWhat went wrong with the first product and how it got fixedUsing AI to match customers with service providersWhy bootstrapping forced better product and leadership decisionsWhat most non-technical founders overlook and how to fix itBuilding trust, quality, and discipline from day one🧠 Guest Links:LinkedIn: Bryan ClaytonInstagram (personal): @bryanmclaytonInstagram (company): @yourgreenpal💬 Let’s Keep the Conversation GoingIf this episode spoke to you, share it with someone who’s ready to build even if they feel underqualified. And don’t forget to follow @deartechpodcast on Instagram for clips, updates, and behind-the-scenes content.

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 talk about how Plank came to be, how Warren bet on the web before it was mainstream, and how his leadership style evolved from scrappy founder to servant leader. We also dive deep into accessibility—not just as a requirement, but as a business advantage—and what it really takes to build a strong, remote-first team that still cares.If you care about digital culture, inclusion, and the long game of building something that lasts, this one’s for you.🔍 Topics We Cover:What sparked Warren’s early interest in media and designThe transition from CD-ROMs to the internet (and how he bet on the right thing)The origins and mission behind PlankWhat it means to run a B Corp in techWhy accessibility is a strategic advantage, not just a checklistPractical advice on building an inclusive design processLeading a remote team and creating a real culture without an officeServant leadership in action—and how Warren sees his role evolvingHow AI is changing workflows (and what he’s skeptical about)The future of Plank and building with intention🧠 Quote to Remember:“Accessibility isn’t something you tack on at the end. It’s part of how you design for real people, from the start.”🔗 Resources & Links:Plank Website: https://plank.coCulture Page: https://plank.co/en/cultureWarren’s Blog & Personal Site: https://warrenwilansky.com📣 Connect with Us:Follow @deartechpodcast on InstagramSubscribe and listen on your favorite podcast appLeave a review if this episode resonated with you!

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 about the future of men’s health. This conversation spans medicine, sextech, personal performance, and the importance of taking your health — and pleasure — into your own hands.🔍 In this episode:Dr. Justin’s journey from ER doctor to startup founderWhy most ED treatments are solving the wrong problemThe real reason your erection fades with age (it’s not what you think)How the Tech Ring collects and interprets data overnightWhy sexual health should be tracked like blood pressureThe importance of wearables in preventative medicineFirmTech’s research with Mount Sinai, Baylor, UCSD, and moreWhat women’s clitoral health has to do with the next frontier of this techWhy pleasure and science don’t have to be separate🏆 FirmTech Recognition:FDA-registered Class II medical deviceFSA/HSA eligible7 published research papers, 15+ ongoing clinical studies2023 CES/Showstopper Health Innovation Runner-Up2023 XBIZ Most Innovative Sex Toy of the Year💥 Dear Tech Listener Exclusive:Get 15% off the Tech Ring with code DEARTECH at myfirmtech.com

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 businesses. From misunderstood branding efforts to tactical misfires, Angelo shares lessons from decades of helping companies clarify their message and build smarter go-to-market strategies.This conversation goes deep into the challenges that founders and leadership teams face when they’re scaling — and why strategy should never be an afterthought.What You’ll Learn:Why “build it and they will come” rarely worksThe difference between branding, identity, and positioningWhen it’s time to bring in a fractional CMOHow to align your marketing and sales efforts for real growthMistakes startups make when they try to scale too fastRed flags Angelo watches for before taking on a clientThe marketing blind spots that derail M&A readinessLessons for anyone thinking about going fractionalGuest: Angelo PonziAngelo Ponzi is a fractional CMO and brand strategist with over 25 years of experience helping companies strengthen their market presence, prepare for acquisition, and grow revenue through smarter marketing. He’s worked across industries, from early-stage startups to $100M+ firms, and brings a deeply strategic approach to everything from messaging to execution. Find Angelo here:🔗 linkedin.com/in/angeloponzi🌐 https://www.craftmarketingandbranding.com/Stay Connected with Dear Tech: 📸 Instagram: @deartechpodcast🔗 Linktree: thedeartechpodcast💼 LinkedIn: Dear Tech Podcast

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 shares stories from Estenda’s early work with the Department of Defense and the VA, explains how wearable tech is changing chronic care, and reveals why real transformation in medicine is as much about people and process as it is about technology.We also talk triathlons, startup roadblocks, and RJ’s personal productivity framework, Productive Harmony, which explores how energy—not time—is the key to doing meaningful work without burning out.What We CoverThe evolution of AI in clinical settingsWhy most EMRs still frustrate doctorsHow ambient listening is changing note-taking in medicineThe role of wearables in aging and chronic careWhat startup founders in medtech need to know before buildingRJ’s book Productive Harmony and the case for energy over timeThe surprising connection between triathlon training and running a businessAbout the GuestRichard Kedziora is the Co-Founder of Estenda Solutions, a healthtech company focused on building data-powered tools that improve wellness and care outcomes. He holds a B.S. in Computer Science from Duquesne University and an M.B.A. from West Chester University of Pennsylvania, and he’s presented at countless technical and healthcare conferences. RJ is also an endurance athlete and the author of the upcoming book Productive Harmony.Resources & MentionsEstenda SolutionsRJ’s LinkedInFollow RJ on Instagram @productiveharmonyBook: Productive Harmony (coming soon)Follow Dear Tech📸 Instagram: @deartechpodcast🔗 Website: linktr.ee/thedeartechpodcast💼 LinkedIn: Dear Tech Podcast

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 her to leave the corporate world, and the unexpected challenges of entrepreneurship.We explore:Why she walked away from corporate life and how she built Cadra from the ground upWhat makes cybersecurity compliance so misunderstood (and often neglected)Surprising gaps in how small businesses think about IT and securityThe importance of making technical work human and understandableFedRAMP, NIST, CMMC, and the real-world impact of regulatory frameworksWhat AI means for cybersecurity compliance — and what’s coming nextThe human side of leadership, working remote, and managing a values-driven teamHer mentorship philosophy, favorite client wins, and… the time she met a hard drive that had been shot with a bulletPlus, we talk dogs, Harry Potter houses, and why “you are good enough” is the sticky note she’d leave for her past self — and maybe for all of us.🎧 Listen now and don’t forget to follow the show.🔗 Learn more about Lori’s work: www.cadra.com📲 Connect with Lori on LinkedIn: https://www.linkedin.com/in/lori-crooks

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&nbsp;Dapper No-Code&nbsp;— 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 how white-labeling platforms can fuel your launch.We also talk about wine making (yes, really), podcasting, dogs, and the future of AI-powered development.What You’ll LearnWhy Dan pivoted from helpdesk support to founding a no-code companyThe difference between “having an idea” and building a businessWhat people misunderstand about no-code tools in 2025Dan’s process for validating app ideas (hint: it started at Planet Fitness)The role of&nbsp;white labeling&nbsp;in scaling Dapper No-CodeHow Dan's "Fast Track" offering takes apps from idea to launch in 90 daysWhere AI is supercharging app creation—and where it’s falling shortThe evolution of podcasting and how Dan's show&nbsp;Tech Bytes&nbsp;became a key growth leverDan’s episode with&nbsp;Alex SanfilippoDan’s journey into winemaking, how he does it at home, and what flavors he’s experimenting withThe surprising impact of mentorship and what Dan teaches the next generation of no-code developersBig thoughts on saturation, technical debt, and what enterprise adoption of no-code could look likeMentions &amp; ResourcesDapper No-CodeBubbleZapierPodMatchDan’s episode with&nbsp;Alex SanfilippoAtomic Habits by James ClearHigh Performance Habits by Brendon BurchardBackendlessRapid Fire FavoritesFavorite quote:&nbsp;“Done is better than perfect.”Most gifted book:&nbsp;High Performance HabitsFavorite investment:&nbsp;“Continually investing in myself”Best thing he’s been gifted:&nbsp;A bartered coaching programBillboard message:&nbsp;“Your focus determines your reality.”Something he changed his mind on recently:&nbsp;The idea of contentment vs constant hustleFun ExtrasDan brews wine in his basement — his latest batch? Peach.He has three dogs, including a golden retriever-aussie mix with blue eyesShubho and Dan swap stories on podcasting, dogs, and why “apps aren’t the business”Follow &amp; ConnectDapper No-Code Website<a href="https://www.linkedin.com/in/dan-hafner-35066a39/" rel="noopener noreferrer"...

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 everything in between. Season One held space for the full spectrum of what it means to build a career today.🎧 In this episode, you’ll hear: • 🔥 Unfiltered takes on the interview process and hiring realities • 💼 Real-life negotiation strategies (and what not to do) • 🧠 Insights on company culture, internal equity, and employee experience • 💬 Stories of career pivots, risk-taking, and reclaiming control • 💡 Tangible advice from people who’ve lived the ups and downs of tech🙏 A huge thank you to our featured guests:Sanjit, Elle, Dev, and Tahmid. Thank you for your brilliance, your stories, and your honesty.And to my amazing co-host Francesca, this season wouldn’t have been what it was without you.Whether you’ve been riding with us since day one or this is your first listen, this episode is for you. Let’s take a moment to reflect on everything Season One gave us, and everything still to come📲 Connect with us:📸 Instagram: @deartechpodcast🔗 LinkedIn: Dear Tech Podcast🌐 Website &amp; Links: linktr.ee/thedeartechpodcast🎧 Listen wherever you get your podcasts — and don’t forget to subscribe, rate, and share if this one resonated. 💛

Episode Summary:In this episode of&nbsp;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 tech enthusiast, or someone looking to improve resilience and adaptability, this episode has something for you.Key Topics Covered:1. Sailing and Its Parallels to Startups&nbsp;(00:01:42 - 00:07:42)How Taylor discovered sailing and its impact on his personal growth.The endurance, teamwork, and adaptability required for offshore racing.The connection between sailing and startup leadership—navigating changing conditions, team dynamics, and goal setting.2. The Evolution of Ambient&nbsp;(00:07:42 - 00:15:12)The origin of Ambient from a pre-pandemic startup focused on live events.Pivoting to virtual event networking during COVID-19.Identifying the shift in remote work trends and transitioning towards AI-powered workflow automation.How Ambient supports chiefs of staff, founders, and operations leaders with AI-driven insights.3. Building AI-Driven Products in a Crowded Market&nbsp;(00:15:12 - 00:23:12)Differentiating Ambient by focusing on a specific persona: the Chief of Staff.Understanding the balance between AI capabilities, user expectations, and reliability.How AI is reshaping the SaaS industry and pricing models.4. Startup Mindset: Lessons from a Three-Month Contract to Co-Founding&nbsp;(00:23:12 - 00:32:12)Taylor’s journey from a temporary contract at a tech company to becoming a startup co-founder.The importance of curiosity, ownership, and building a strong network.How non-technical professionals can successfully transition into tech roles.5. Psychological Flexibility and Mental Fitness&nbsp;(00:32:12 - 00:47:42)Understanding psychological flexibility and its role in decision-making and resilience.The connection between physical and mental fitness in high-pressure environments.Taylor’s personal strategies for preventing burnout, including sailing, breathwork, and slowing down.The importance of modeling work-life balance as a leader.6. The Future of Remote Work&nbsp;(00:47:42 - 01:03:12)Balancing flexibility with in-person collaboration.Why remote work benefits some roles but not others.The impact of company culture on remote and hybrid work success.FAQs with Taylor:&nbsp;(01:03:12 - 01:18:12)Best advice ever received?"Slow down." Taking a breath and avoiding knee-jerk reactions helps in high-pressure situations.Best investment?Teaching others how to sail—it’s about passing on knowledge and building relationships.Best gift ever received?A love for music, instilled by his father.One message for a billboard?"Just breathe."Most recommended book?The Alchemist&nbsp;by Paulo Coelho.What’s Next for Taylor?&nbsp;(01:18:23 - 01:25:12)Scaling Ambient and continuing to develop AI-driven solutions for operations leaders.Upcoming sailing races, including the Aegean 600...

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 - Intro00:20 - Kicking off - how do Sanjit and Shubho know each other05:16 - the love of tech is generational 8:35 - Sanjit is not a coder11:42 - what Sanjit does today12:58 - What got Sanjit to where he is today (motivation &amp; Path)17:42 - Working at a start up vs working at a large enterprise20:28 - Motivations going into the MBA program23:31 - Coming from tech, who would you recommend and MBA program to, who would you dissuade? 28:45 - Education vs Work experience when looking to hire33:30 - Deep dive into Sanjit's time consulting39:20 - Sanjit's thoughts on being a Startup founder one day43:06 - How Sanjit views work and career to his Identity as a person50:03 - Whats Sanjit's work life balance like right now? (hobbies) 56:07 - Chief of Staff network58:50 - The value of networking01:02:50 - How to plan for a job in consulting 1:09:56 - Work experience before getting an MBA01:13:17 - What would 15 year old Sanjit think of where you are and your journey?01:14:39 - Dear Tech FAQs--This production may contain views and opinions which are those of the authors and&nbsp;do not necessarily reflect the official policy or position of any other&nbsp;author, agency, organization, employer or company.

Elle Anderson Joins our host Fran &amp; 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.

00:20 - Welcome01:55 - What is LinkedIn07:43 - Utilization from a company perspective08:07 - How is LinkedIn best utilized?14:48 - Candidate Profiles15:01 - Profile Picture22:29 - LinkedIn Headline29:40 - How much detail do you put into your work history? 33:23 - What experience can you add to your profile besides work experience?35:46 - Remove dates from education!!!38:18 - Certifications on LinkedIn40:11 - Engagement on the platfrom43:13 - Use LinkedIn to educate yourself44:20 - Shubho might be a linkedIn snob lol 49:45 - Shubho's rant - advice on what not to do when making a sales call51:49 - Three templates of reaching out to people on LinkedIn. 52:34 - (Template 1) Candidates looking for jobs56:40 - (Template 2) Sales people trying to get new business59:21 - (Template 3) Recruiters reaching out to candidates. 01:01:47 - Fran's take01:19:10 - How companies can best utilize and leverage the LinkedIn Platform01:14:28 - If you have nothing nice to say dont say anything at all01:18:33 - Wrap up

Fran and Shubho discuss compensation negotiation from the perspectives of the candidate, employer, and the (current) employee. They dive into what can be expected during negotiations and how to improve over all negotiation tactics. --00:20 - Welcome01:27 - how does Shubho Negotiate &nbsp;01:44 - book recommendation&nbsp; Never Split the Difference, by Chris Voss09:43 - How does Fran negotiate17:38 - Negotiating with recruiters&nbsp;25:05 - talking to multiple companies/multiple&nbsp;28:40 - What good tools and resources when going into a negotiation?33:27 - the recruiter can be your ally37:11 - Closed mouths don’t get fed47:15 - Negotiating inside your current company49:56 - Negotiating Severance?!52:58 - Take your time signing paperwork54:56 - Negotiate from a position of strength56:43 - What should companies be mindful of when extending offers?&nbsp;01:06:43 - Shubho’s two’s pieces of advice01:10:56 - Frans take&nbsp;01:12:09 - Wrapping up

00:20 - Welcome09:39 - RTO vs WFH from a employee perspective18:44 - RTO vs WFH from a leadership perspective23:00 - Articles Fran referencedhttps://news.bloombergtax.com/tax-insights-and-commentary/tax-considerations-of-remote-work-arrangements-around-the-worldhttps://www.bloomberg.com/news/features/2023-02-21/another-threat-to-work-from-home-tax-breaks31:56 - Fran's Personal experience with remote work and her health33:32 - Frans take on what to do first when making a change to remote work policy for a company. 35:33 - Shubho's hot take 39:02 - What would get Shubho in the office? 46:05 - Finding a company that fits the life you want47:56 - Wrap up

Fran and Shubho discuss the steps to recovery after being impacted by layoffs.00:00 - Welcome02:39 - Effects of LinkedIn on the overall tech workforce 07:17 - Shubho's experience with being laid off15:23- Shubho shares what helped him get through the time, shares advice21:07 - Processing your situation22:34 -Taking action26:42 - Being able to stay flexible and transition 31:47 - The importance of networking39:30 - Is going back to school a good idea if you get laid off47:16 - Being confident and having a support system

Fran and Shubho Discuss Perks vs. Benefits in today's job market and how companies can lean into their strengths when it comes to what they can offer. 00:39 Intro00:56 Fran &amp; Shubho's experience with Perks03:43 Defining Perks vs Benefits13:10 Companies utilizing perks when they can't pay large salaries20:41 Change over the years29:57 Effects of COVID on Perks and Benefits - and remote work36:28 "If a company is doing it right what are they doing today?" - Shubho's take45:06 Fran's take48:19 How generational norms have affected Perks and benefits59:55 The evolution of supply and demand in the tech industry has affected, if at all, workplace perks.01:04:00 Potential effects of supply and demand01:06:13 Stats on perks and benefits01:09:57 Fran's Top Perks &amp; Benefits01:12:20 Shubho's top perks &amp; Benefits01:15:12 Shubho's takeaways01:16:59 Fran's takeaways01:18:51 Wrap up

00:36 Introduction01:13 Defining quiet quitting03:57 Defining quiet quitting8:25 How Fran Sets Boundaries9:51 How Shubho Sets boundaries 11:19 How do people define Quiet quitting13:53 Meet people where they are15:08 People turning down promotions?117:06 Frans experience turning down a promotion20:40 Is quiet quitting good or bad?23:06 People have different priorities 25:43 How should leaders go about quiet quitting28:19 Taking on more responsibilities when trying to get promotions31: 24 Shubho's take if quiet quitting is bad, and leadership perspective 33:42 Quiet quitting comes down to your values35:56 Advocate for your teams!36:52 Wrapping up

Fran and Shubho discuss the current job market &amp; economy in tech and how we got here from the beginning of the pandemic.

Fran and Shubho discuss todays interview landscape and what they think are the good, the bad, and the ugly.

Fran and Shubho discuss who they are, What they are intending to accomplish on this podcast and why they decided to start this project.