The Stash Cast

In this episode of The Stash Cast, I sit down with Samarth Bhalla, operator-turned-investor and founder of Trevi, a fashion-tech AI startup that’s reimagining how we shop, dress, and engage with brands.

Samarth shares his journey from consulting for Fortune 500 companies to building breakout Indian startups (including one now heading for IPO), and launching a virtual stylist powered by generative AI. Now an MBA at UCLA Anderson and a Portfolio Manager for its impact venture fund, he offers a unique dual lens as both founder and investor.

We explore:

* The problem Trevi is solving — and why fashion needs a digital memory

* What a real moat looks like in the age of ChatGPT

* A crash course in impact venture capital and catalytic investing

* How cocoa supply chains, cow-trading apps, and influencer UX connect

* Turning data, not products, into defensible SaaS businesses

A wide-ranging conversation filled with actionable insight for VCs, founders, and builders operating at the intersection of AI, commerce, and impact.

In this episode, Brian Esposito — founder of Esposito Intellectual Enterprises and CEO of Diamond Lake Minerals (DLMI) — shares how he's helping bring institutional credibility and scale to tokenization.

We explore:

* Why $7T in maturing CRE debt poses massive risk — and opportunity

* How security tokens can create liquidity for trapped LPs and stalled assets

* Why gimmicky one-off token projects fail

* His blueprint for a regulated token exchange tied to real-world assets

* How tokenization could democratize ownership in hotels, media, aviation & more

* Advice for founders on raising capital, building momentum, and cutting dead weight

If you care about the future of real estate, digital securities, or startup execution — this one’s loaded with insight.

In this episode of The Stash Cast, host Stash sits down with Ivan Klyzhenko, founder of a global SaaS product design agency, to talk about what it really takes to build great software for real businesses — not just shiny startups.

Ivan shares his journey from writing code at 17 to leading high-impact UI/UX projects for ERP and CRM platforms in industries like healthcare, construction, fleet management, and real estate. They discuss:

* Why “simple” design is often the most powerful

* The importance of working with people you actually like

* Why older, established B2B companies are his sweet spot

* How bad UX is killing good products

* The surprising role of tractors, cow tracking, and excavators in modern software

* And why real buttons (yes, physical buttons) might be due for a comeback

If you care about product design, user experience, or how tech is transforming legacy industries, this one’s for you.

In this episode, Carter Olles, co-founder of Nautilus, unpacks his journey from leading nearly $1B in real estate transactions at MLG to launching his own firm. We dive into how Carter evaluates deals quickly and conservatively, why many acquisitions go wrong, and his thesis for targeting high-quality, newer multifamily assets in the Midwest. He also shares thoughts on current market conditions, risk management, and the future of multifamily investing. A must-listen for anyone in real estate acquisitions, private equity, or capital markets.

In this episode of The Stash Cast, we sit down with Lee Hoffman — a seasoned entrepreneur and the co-founder of Runwise, the company transforming how buildings operate. Lee shares his journey from startup failures to building a tech platform that powers over 10,000 buildings across the U.S., making them smarter, safer, and more energy-efficient.

We dive into why real estate has been historically slow to adopt new tech, how Runwise cracked the code on affordable retrofits, and what it really takes to scale a hardware-software startup in one of the most challenging industries. From bootstrapping to raising venture capital and developing 10-year battery-powered wireless sensors, Lee walks us through every gritty and game-changing step of the journey.

If you’ve ever wondered how a 50-story building gets a tech upgrade — or how to pitch a solution no one knew they needed — this episode is a must-listen.

In this personal and tech-forward episode of The Stash Cast, host Stash dives into heritage, hustle, and high-tech with John Reilly — a seasoned investment banker turned CEO of PGE Inc.

John opens the show with a powerful look at his Irish ancestry, tracing the lineage of the O'Reilly clan back to kings, castles, and coat-of-arms lore. Then, he shifts gears and takes us on a journey through his eclectic career — from practicing Chinese medicine to building wealth management firms and leading innovation in the proptech space.

Now at the helm of PGE Inc., John shares how his team is using multi-agent generative AI to completely transform the apartment rental experience — from automated listing creation and personalized marketing to conversational leasing agents and predictive maintenance coordination.

This episode is a rare mix of legacy and future, roots and disruption — perfect for anyone curious about how deep experience and emerging technology can converge to reshape real estate.

🎙️ Stash Cast with Lee Kiser | Inside the Mind of a Multifamily Brokerage Leader 🏢

In this episode of Stash Cast, we sit down with Lee Kiser, Co-Founder, Principal, and Managing Broker at Kiser Group, for a wide-ranging, candid conversation about the evolution of multifamily real estate, building a values-based brokerage, and where the industry is headed.

Lee shares his journey from founding a boutique real estate firm in Chicago with his wife to expanding across multiple states—including Illinois, Indiana, Wisconsin, Michigan, and Ohio—with a new office in Minneapolis. With nearly three decades in the industry, Lee dives deep into what it really takes to build trust, outwork the competition, and lead with integrity in a notoriously cutthroat market.

Whether you're a broker, investor, or entrepreneur, this episode offers a rare behind-the-scenes look at what separates lasting success from fleeting wins in real estate.🔍 Key Insights:

* Culture is Everything: Kiser Group was built on a strict “no-jerk” policy—prioritizing collaboration, transparency, and mutual respect across all hires.

* Client-First Mentality: Putting the client's interests above all else—even if it means walking away from a deal—creates loyalty that lasts decades.

* Market Differentiation: In Chicago, mid-market firms like Kiser Group outperform larger national names through niche specialization and hyper-local knowledge.

* Architectural Intelligence: Understanding physical property characteristics (like vintage plumbing or “four-plus-one” construction) can reveal hidden risks and opportunities during underwriting.

* Tech + Grit = Advantage: While larger firms may offer scale, smaller firms like Kiser Group bring relentless hustle, sharper analysis, and a personal touch.

* Future of Brokerage: AI, machine learning, and blockchain will transform real estate—but not replace the human insight, empathy, and nuance required in high-stakes deals.

✅ Takeaways:

* Don’t Compromise on Principles: Clear values like “clients first” and “no egos” provide the foundation for lasting success in any brokerage firm.

* Avoid the Off-Market Hype: Deals without transparency often come with higher risks and less value. True market pricing comes from real competition.

* Data is Power: Tracking every interaction, lead, and conversion sharpens strategy and improves outcomes—for both clients and brokers.

* Train Like You Mean It: Kiser Group’s training library includes thousands of hours of customized videos and resources, tailored to each agent’s market and role.

* Growth Should Be Purposeful: Expansion isn’t about size—it’s about bringing the right platform to the right talent in the right markets.

* Adapt or Fade: While real estate is still about people, the most successful firms will be the ones that evolve with technology—without losing their human edge.

📌 Whether you're breaking into the industry or refining your edge, this episode will challenge, educate, and inspire you.

👀 Watch now and gain timeless insight from one of the Midwest’s most respected real estate leaders.

In this insightful episode of Stash Cast, host Stash sits down with John Wijtenburg to unpack his journey through the financial crisis, commercial real estate, and building scalable businesses.

John shares hard-earned wisdom from scaling an eight-property hotel portfolio to now helping real estate entrepreneurs break past growth ceilings. Whether you're in hospitality or any investment-focused business, John’s approach to systems, strategy, and mindset offers game-changing insights.

✅ Key Takeaways:

💼 How John transitioned from residential real estate to commercial and hotel investing.

📈 What it's like building a hotel portfolio from scratch—while navigating market shifts.

📊 The operational intensity of hotels vs. other real estate asset classes.

🛠️ Why systems, SOPs, and execution frameworks are critical to scaling past 5–8 properties.

🧱 Why most founders need to shift from “being the business” to building the business.

🌎 How John built a 30-person offshore team to manage HR, compliance, legal, and more.

💬 The value of daily huddles and two-week sprints to create engagement in remote teams.

💡 Insights:

🧠 Vision → Strategy → Execution: Success starts with clarity of vision, which drives team alignment and operational decisions.

🔍 Double Diamond Framework: Avoid chasing shiny tools—solve real problems by first identifying root causes, then tailoring solutions.

⚙️ Use content as leverage: Beyond capital and code, content attracts talent, defines culture, and communicates your values.

🏨 Hotels are operating businesses first: Investors often underestimate how fast the cycle time is—and how fast things can go wrong.

📉 Don’t let your underwriting become gospel: Annual strategy resets lead to smarter, more adaptive operations.

🌐 AI, automation, and remote talent can transform productivity—if paired with the right culture and cadence.

🔥 Burnout is common at every level: Even $1B+ portfolios can fail if leaders don’t build systems that reduce decision fatigue.

💬 Whether you're a student, young professional, or someone just starting your wealth journey, John's candid insights and personal stories offer a refreshing and grounded perspective on finance.

🚀 How Not to Screw Up Your Startup – Hard-Earned Advice from VC Andrew Ackerman

In this episode of Stash Cast, Andrew Ackerman is back with raw, practical startup advice drawn from 70+ investments, 100+ coached founders, and two startup exits. He shares the real reason most founders fail—and what he’s doing about it with his new book A Novel Approach to Startups.

📘 This is not your average business book. Inspired by The Goal, Andrew’s novel delivers startup lessons through story, making it easier to remember and apply when it counts.🔍 Insights:

* Most startup education fails because it’s boring, disconnected, or delivered out of order

* Cold emails to VCs almost never work—they signal laziness, not hustle

* Startups are enterprise sales: the same planning, targeting, and positioning applies

* Great storytelling outperforms slides and spreadsheets when teaching real-world business skills

* Your co-founder matters as much as your idea—get that decision wrong and everything else crumbles

✅ Key Takeaways:

* Focus on warm intros and building investor relationships early—not just when you need funding

* Cold calling works (if you do the research); cold emailing does not

* Don’t pitch—ask great questions. The best meetings are conversations, not monologues

* The right investor is a long-term partner, not just a check

* Every founder should be spending 20–80% of their time fundraising—depending on stage

* Learn to teach your processes: if you can teach it, you understand it

🔔 Subscribe to Stash Cast for more honest conversations with founders, VCs, and operators building the future.

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In this episode of The Stash Cast, Jake and Stash dive deep into the rollercoaster journey of entrepreneurship, mental health, and staying authentic in the creator economy. From navigating the chaos of brand building to the discipline required to stay consistent, this episode is a must-watch for creatives, business owners, and anyone chasing passion over paycheck.

🎙️ Key Topics Covered:

The importance of consistency in building a brand

Balancing creative work with business demands

Navigating burnout and self-awareness as a creator

What it really takes to make your passion sustainable

Why honesty and transparency matter in podcasting and business

💡 Key Takeaways:

Start messy, then refine – you don’t need to be perfect to begin.

Burnout is real – knowing your limits and resetting is key to longevity.

Storytelling and transparency are more valuable than polished perfection.

Discipline beats motivation – especially when your name is your brand.

The journey is the reward – every failure is a step toward clarity.