What if your fundraising edge isn’t a prettier deck, but the energy you bring into the room? We sit down with Miami operator and “crypto guy” Kyle Sonlin to unpack how conviction, curiosity, and consistent behavior become the signals investors actually trust. The journey winds through a decade of Miami tech growth, the post-remote shift in capital access, and why in-person time still matters when you’re reading character and momentum.

Kyle pulls back the curtain on tokenization in plain language: move cap tables to a shared digital ledger, compress the compliance burden, and make private markets more liquid without ditching guardrails. He connects this with the JOBS Act’s broader investor base and explains why automation is no longer a nice-to-have when you’re handling cross-border investors at scale. Then we get tactical: how he reversed the pitch by collecting buy-side mandates first, why family offices decide differently than VC funds, and how “side quests” become the hidden gateway to real checks.

The standout story is a $75 million oil refinery acquisition completed with a crypto-to-fiat bridge in minutes, solving a payments headache that would have dragged for months through traditional rails. From there, Kyle outlines Global Settlement’s capital stack and strategy—multi-layered SAFEs, deal-specific SPVs, a network token aligned with clarity on the rules, private credit and trade finance, and a fully backed digital dollar to move money globally with speed and compliance. Threaded through it all is tenacity: flying to Asia on a credit card, rebuilding during a dry market, and betting on a thesis grounded in real-world frictions and practical tech.

If you’re a founder or investor navigating family offices, cross-border capital, or the future of private markets, you’ll walk away with a playbook that is equal parts relationship and rigor. Subscribe, share this with a friend who’s raising, and leave a quick review telling us the biggest financing bottleneck you want solved next.

Connect with Keith on LinkedIn - https://www.linkedin.com/in/keithkohler1/

What if your financing strategy was as clean and simple as your ingredient list? We sit down with Hector Gutierrez of JOI, the plant base brand built on “just one ingredient,” to unpack how a concentrated product, a flexible channel mix, and disciplined cash flow turned a pre-pandemic seed round into a profitable, resilient business. From the early days of almond paste sold B2B to cafés to a brand platform that spans DTC, Amazon, foodservice, and select retail, this is a masterclass in using the right capital at the right time.

Hector walks us through the investor dinner that galvanized their seed raise, the overnight shift when foodservice collapsed and e-commerce exploded, and the systems they put in place—3PL, Amazon, Shopify—to capture demand. We dig into the real numbers behind growth capital: merchant cash advances, Amazon and Shopify lending, AR financing, and how to decide between fixed or percentage remittances. The tactical takeaway is clear: map your cash cycles by channel, prioritize suppliers to protect inventory, and let your model decide the instrument.

We also get personal about the psychology of fundraising. Scarcity vs abundance, valuation vs dilution, and why “raise because you can” can backfire if the fit isn’t right. JOI’s approach favors profitability as leverage, retail as a credibility and awareness play, foodservice as a margin engine, and DTC as a data-rich community channel. With new products rolling out, partnerships with Whole Foods and Target, and foodservice formats designed for speed, JOI proves that resilience is a strategy you can scale.

If this helped you think differently about capital, channels, or unit economics, follow the show, share it with a founder who needs it, and leave a quick review so more builders can find these conversations.

Connect with Keith on LinkedIn - https://www.linkedin.com/in/keithkohler1/

Keith Kohler launches his new podcast "How I Financed It" with a candid conversation featuring Ora Organic co-founders Ron and Will, who share their decade-long journey from maxed-out credit cards in the beginning to sustainable profitability today.

The founders reveal how their personal motivations—Will's frustration with supplement transparency during his "junk food vegan" days and Ron's family health challenges—fueled their mission to create plant-based, organic supplements with traceable ingredients. Their financing path unfolds like a masterclass in entrepreneurial resilience, starting with $150,000 from friends and family, progressing through SBA loans, and leveraging a Shark Tank appearance to secure a million-dollar convertible note.

What makes this conversation particularly valuable is the founders' transparency about pivoting when necessary. They explain why they scaled back retail operations despite initial success, focusing instead on direct-to-consumer channels where their marketing dollars worked harder. When the pandemic dried up equity markets, they resisted the common advice to "take a hatchet" to their business, instead making incremental efficiency improvements that preserved growth while achieving profitability.

The conversation offers a wealth of practical financing wisdom rarely shared so openly. Will admits he would have "started with the finance side earlier," focusing on profitability from day one, while Ron emphasizes maintaining relationships through difficult times. Their recent equity financing marks not an overnight success but the culmination of calculated decisions, strategic pivots, and unwavering commitment to product quality.

Whether you're bootstrapping your first venture or navigating growth challenges in an established business, this episode delivers invaluable insights into financing options beyond the traditional equity path. Connect with Keith on LinkedIn at Keith Kohler1 to continue the conversation about financing strategies for your business journey.

Connect with Keith on LinkedIn - https://www.linkedin.com/in/keithkohler1/