The Dear Tech Podcast

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 it
• How PortfolioPilot uses AI to eliminate financial bias and offer tailored, transparent recommendations
• The emotional traps people fall into with investing and how AI helps you navigate them
• Real 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 superpower
• The power and misunderstanding of tax-loss harvesting
• The 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 checkout

Resources & Links:

• 💼 PortfolioPilot.com
• 🧠 Alexander on X/Twitter: @alexharm
• 📺 PortfolioPilot on YouTube
• 🧑‍💼 Alexander on LinkedIn
• 📚 Books Mentioned:
• Spin Selling by Neil Rackham
• Crucial Conversations by Patterson, Grenny, McMillan & Switzler

Connect with the Show:

• 💬 Instagram: @deartechpodcast
• 💼 LinkedIn: Dear Tech Podcast
• 🌐 All links: linktr.ee/thedeartechpodcast

If 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.

• Misconceptions about cannabis payments and legality
• Why compliance is a competitive advantage in fintech
• Bootstrapping to profitability without outside investment
• Building PayRio’s team through trust and culture-first hiring
• Processing payments for cannabis, psychedelics, peptides, and more
• Her role on NCIA’s Banking & Financial Services Committee
• Lessons from JP Morgan that still guide her company today
• Balancing motherhood and entrepreneurship under pressure
• The power of showing up authentically in business

• PayRio → https://www.payrio.co
• PayRio on Linkedin →https://www.linkedin.com/company/payrio/
• Instagram → @payrio_hq
• Aubrey on LinkedIn → https://www.linkedin.com/in/aubreyamatelli

If 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.

• The mindset shift from blue-collar business to tech founder
• Teaching yourself to code after building a $10M company
• Cold-calling 500+ vendors to build the first version of the platform
• What went wrong with the first product and how it got fixed
• Using AI to match customers with service providers
• Why bootstrapping forced better product and leadership decisions
• What most non-technical founders overlook and how to fix it
• Building trust, quality, and discipline from day one

• LinkedIn: Bryan Clayton
• Instagram (personal): @bryanmclayton
• Instagram (company): @yourgreenpal

If 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 design
• The transition from CD-ROMs to the internet (and how he bet on the right thing)
• The origins and mission behind Plank
• What it means to run a B Corp in tech
• Why accessibility is a strategic advantage, not just a checklist
• Practical advice on building an inclusive design process
• Leading a remote team and creating a real culture without an office
• Servant leadership in action—and how Warren sees his role evolving
• How 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.co
• Culture Page: https://plank.co/en/culture
• Warren’s Blog & Personal Site: https://warrenwilansky.com

📣 Connect with Us:

Follow @deartechpodcast on Instagram

Subscribe and listen on your favorite podcast app

Leave 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.

• Dr. Justin’s journey from ER doctor to startup founder
• Why most ED treatments are solving the wrong problem
• The real reason your erection fades with age (it’s not what you think)
• How the Tech Ring collects and interprets data overnight
• Why sexual health should be tracked like blood pressure
• The importance of wearables in preventative medicine
• FirmTech’s research with Mount Sinai, Baylor, UCSD, and more
• What women’s clitoral health has to do with the next frontier of this tech
• Why pleasure and science don’t have to be separate

• FDA-registered Class II medical device
• FSA/HSA eligible
• 7 published research papers, 15+ ongoing clinical studies
• 2023 CES/Showstopper Health Innovation Runner-Up
• 2023 XBIZ Most Innovative Sex Toy of the Year

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 works
• The difference between branding, identity, and positioning
• When it’s time to bring in a fractional CMO
• How to align your marketing and sales efforts for real growth
• Mistakes startups make when they try to scale too fast
• Red flags Angelo watches for before taking on a client
• The marketing blind spots that derail M&A readiness
• Lessons for anyone thinking about going fractional

Guest: Angelo Ponzi

Angelo 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 Cover

• The evolution of AI in clinical settings
• Why most EMRs still frustrate doctors
• How ambient listening is changing note-taking in medicine
• The role of wearables in aging and chronic care
• What startup founders in medtech need to know before building
• RJ’s book Productive Harmony and the case for energy over time
• The surprising connection between triathlon training and running a business

About the Guest

Richard 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 & Mentions

• Estenda Solutions
• RJ’s LinkedIn
• Follow RJ on Instagram @productiveharmony
• Book: 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 up
• What makes cybersecurity compliance so misunderstood (and often neglected)
• Surprising gaps in how small businesses think about IT and security
• The importance of making technical work human and understandable
• FedRAMP, NIST, CMMC, and the real-world impact of regulatory frameworks
• What AI means for cybersecurity compliance — and what’s coming next
• The human side of leadership, working remote, and managing a values-driven team
• Her mentorship philosophy, favorite client wins, and… the time she met a hard drive that had been shot with a bullet

Plus, 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 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 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.

• Why Dan pivoted from helpdesk support to founding a no-code company
• The difference between “having an idea” and building a business
• What people misunderstand about no-code tools in 2025
• Dan’s process for validating app ideas (hint: it started at Planet Fitness)
• The role of white labeling in scaling Dapper No-Code
• How Dan's "Fast Track" offering takes apps from idea to launch in 90 days
• Where AI is supercharging app creation—and where it’s falling short
• The evolution of podcasting and how Dan's show Tech Bytes became a key growth lever
• Dan’s episode with Alex Sanfilippo
• Dan’s journey into winemaking, how he does it at home, and what flavors he’s experimenting with
• The surprising impact of mentorship and what Dan teaches the next generation of no-code developers
• Big thoughts on saturation, technical debt, and what enterprise adoption of no-code could look like

• Dapper No-Code
• Bubble
• Zapier
• PodMatch
• Dan’s episode with Alex Sanfilippo
• Atomic Habits by James Clear
• High Performance Habits by Brendon Burchard
• Backendless

• Favorite quote: “Done is better than perfect.”
• Most gifted book: High Performance Habits
• Favorite investment: “Continually investing in myself”
• Best thing he’s been gifted: A bartered coaching program
• Billboard message: “Your focus determines your reality.”
• Something he changed his mind on recently: The idea of contentment vs constant hustle

• Dan brews wine in his basement — his latest batch? Peach.
• He has three dogs, including a golden retriever-aussie mix with blue eyes
• Shubho and Dan swap stories on podcasting, dogs, and why “apps aren’t the business”

• Dapper No-Code Website
• Dan’s LinkedIn
• Dear Tech on Instagram
• Dear Tech on LinkedIn
• Dear Tech Website

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 & Links: linktr.ee/thedeartechpodcast

🎧 Listen wherever you get your podcasts — and don’t forget to subscribe, rate, and share if this one resonated. 💛