Unlikely Success

About Unlikely Success

The Unlikely Success podcast presents stories of people who made it against the odds. Some are in fields where the odds of making it to the top are like winning the lottery, others overcame hurdles in their personal lives, and still others picked an industry that society does not equate with opportunity.

Publisher

Jeffrey Koenig

Category

business · business

Language

en

Explicit

No

First episode

11 Jun 2026

Latest episode

15 Oct 2026

Latest episodes

18 episodes in the feed.

1. 

   15 Oct 2026

   Equity Research Didn't Inspire Her. Kids' Birthday Parties Did - Julie Tylman

   Ep. 18 Equity Research Didn't Inspire Her. Kids' Birthday Parties Did. - Julie Tylman Julie Tylman built her career on numbers. She worked across sales, IT consulting, and equity research in the US, Europe, and Australia, and earned an MBA from Columbia University. None of that is what started her company. What started it was the kids' birthday party circuit: years of chasing other parents for cash, tracking who had signed the card, and spending far too much money on gifts nobody coordinated. She and her co-founder, Ali Linz, decided there had to be a better way to organise a group gift, so they built one. Her finance background didn't become the idea. It became the backbone that turned the idea into a real business. That business is GroupTogether, a group gifting platform that lets people pool contributions for gifts, sign group cards, and coordinate workplace gifting for employee recognition, team celebrations, and milestone occasions. What began in their local community now serves individuals, small teams, and large organisations across Australia and the United States, with thousands of companies using the platform. Covid was a turning point: remote teams used GroupTogether to farewell colleagues, welcome new arrivals, and stay connected, which accelerated the company's move into workplace gifting. Julie gets into the mechanics most founders gloss over: owning the financials behind the pitch deck, managing fraud, compliance, and payments across two countries with different regulatory environments, bridging marketing and engineering, and embedding AI into how her team actually works. She also talks openly about what it takes to run a business with a co-founder for more than a decade. Her story is proof that the best business ideas often come from everyday frustrations, and that the right background is what turns them into something lasting. Connect with Julie: Website > https://www.grouptogether.com LinkedIn > https://www.linkedin.com/in/julie-tylman-8a160977/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

2. 

   8 Oct 2026

   The Skate Shop Was the Business. The Website He Built for It Became the Career. - Jerad Hill

   Ep. 17 The Skate Shop Was the Business. The Website He Built for It Became the Career. - Jerad Hill Jerad Hill has been working for himself since he was 10 years old, running a lemonade stand stocked with lemons from his neighbor's tree. At 20 he opened a skateboard shop, and because he wanted to sell online, he taught himself to build websites. It was a side skill picked up out of necessity, meant only to support the shop. Instead, it quietly became the foundation for everything that came after. Building his own site led to building sites for other people, which pulled him into photography, and each new skill opened the door to the next business. That chain turned into a digital marketing agency, a WordPress plugin company, two YouTube channels past 100K subscribers, and online courses that have reached more than 450,000 students. Jerad talks about what it takes to stay self-employed for nearly 30 years, and how he has kept reinventing his work as the internet changed around him. His story is proof that the skill you pick up to solve one small problem can end up building your entire career. Connect with Jerad: Website > https://jeradhill.com Courses > https://courses.jeradhill.com YouTube > https://www.youtube.com/@jeradphoto Instagram > https://www.instagram.com/jeradhill/ LinkedIn > https://www.linkedin.com/in/jeradhill/ Substack > https://substack.com/@jeradhill More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

3. 

   1 Oct 2026

   The Marines Taught Him to Follow Orders. Homeowners Taught Him to Take Them - Brad Huebner

   Ep. 16 The Marines Taught Him to Follow Orders. Homeowners Taught Him to Take Them. - Brad Huebner Brad Huebner is a Marine from Southern Indiana, and the Corps showed him what leadership, grit, and determination actually look like. It didn't prepare him for a career spent taking orders from homeowners. After working a string of jobs, Brad founded a high-end handyman and residential remodeling company and grew it into a business that completed more than 2,500 jobs for over 900 customers. Being great at the work and being great at the business turned out to be two very different things. Brad talks candidly about the moment he realized other contractors with the same model, in the same market, were succeeding while he was stuck. He also talks about the uncomfortable conclusion that followed: the problem wasn't the market, it was him. Learning the business of building, not just the craft, is what broke the cycle. Today, through Hammer & Grind, he coaches contractors on pricing, sales, marketing, and leadership, and helps them escape the crazy cycle of struggle so they can build companies with integrity. He brings the same passion, directness, and humor to this conversation. He also shares his belief that most people fall short not from a lack of effort, but from a lack of knowledge. His story is proof that the skills that get you started are rarely the ones that build the business, and that the rest can always be learned. Connect with Brad: Website > https://www.hammerandgrind.com/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

4. 

   24 Sept 2026

   He Used to Spot Talent for a Living. Now He's Calling Out How Bad We Are at It. - Michael Dowling

   Ep. 15 He Used to Spot Talent for a Living. Now He's Calling Out How Bad We Are at It. - Michael Dowling Michael Dowling spent the early part of his career as a Hollywood talent agent, professionally paid to spot who had "it" before anyone else did. From there his path kept bending: entrepreneur, startup founder, co-founder and CEO of a global market research and data analytics company that he led to a successful exit, corporate executive, executive coach. Different industries, same recurring observation. The people who got promoted, funded, and trusted to lead weren't usually the most capable people in the room. They were the ones who looked the part. That observation became The Unlikely Leader: Breaking the Bias That Keeps Great Leaders Invisible, and it's now the foundation of a broader movement Michael is building through The Collective Rise, his leadership development platform. His argument is blunt: confidence, charisma, pedigree, and visibility get mistaken for leadership constantly, and organizations pay for that mistake by overlooking genuinely capable people who don't fit the familiar mold. Having advised hundreds of leaders and organizations operating in high-performance environments, Michael isn't just naming the problem. He's building the tools to fix how leadership gets identified in the first place. His core belief cuts to the point: leadership isn't absent in most organizations. It's just being overlooked. Connect with Michael: Book > https://amzn.to/3UXxynH Website > https://www.theunlikelyleader.com/ Intagram > https://www.instagram.com/michaeldowling440 LinkedIn > https://www.linkedin.com/in/dowlingmichael/ YouTube > https://www.youtube.com/@michaeldowling9437 More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

5. 

   17 Sept 2026

   His Wrestling Matches Were Scripted. His Career Wasn't. - James Kaatz

   Ep. 14 His Wrestling Matches Were Scripted. His Career Wasn't. - James Kaatz Before James Kaatz built a marketing agency, he built a resume that reads like a dare. Professional wrestler. Firefighter. EMT. Musician. Executive producer of the television show "Ghost Hunting Beauties." Each of those jobs demanded he read a room, adapt on the fly, and perform under conditions that left no room for hesitation. None of it looked like marketing. All of it prepared him for it. Today James is Co-Founder and CEO of Illumination Marketing, an award-winning Houston agency built on a simple premise: most businesses don't have a marketing problem, they have a clarity problem. He's also the founder of SoloCMO, an AI-powered platform that brings SEO, content planning, competitive research, and local marketing into one system, giving business owners the strategy and tools of a full marketing department without having to build one from scratch. Across both ventures, James's approach stays consistent, cut the noise, focus on what actually drives revenue, and build systems that scale. His wrestling matches may have been scripted. Nothing else about his career has been. Connect with James: SoloCMO > https://www.solocmo.io Illumination Marketing > https://www.marketingillumination.com More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

6. 

   10 Sept 2026

   Same Vest, Different World - Kevin Shtofman

   Ep. 13 Same Vest, Different World - Kevin Shtofman Kevin Shtofman spent the first stretch of his career in the buttoned-up world of Morgan Stanley, EY, and Deloitte - the kind of pedigree that's supposed to set you up for a predictable climb. His climb was anything but. Multiple jobs, a lot of hard feedback along the way, more strikeouts than home runs for a long stretch, and a handful of close calls before the wins started to count. Twenty-two years later, he's still wearing the same Patagonia vest. The world around him just changed completely. That path took him from consultant to investor to advisor, speaker, and now a C-level software executive with seven years in the seat. Along the way he's hired and fired teams, raised multiple rounds of capital, opened offices in other countries, and sat on both sides of the table during mergers. His work has carried him to over 100 countries, and today banks, insurance companies, sovereign wealth and pension funds, and private real estate owners and brokers all lean on his knowledge to figure out how to put AI to work in businesses that are built on brick, steel, and long-term assets rather than code. It's a strange thing to watch someone this fluent in spreadsheets and term sheets become one of the most trusted translators between old-line real estate and the AI world trying to reshape it. Kevin will tell you there's still a lot he doesn't know, and that's the part of his story that matters most: the vest never changed, but almost everything else did. Connect with Kevin: LinkedIn > https://www.linkedin.com/in/kevinshtofman/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

7. 

   3 Sept 2026

   Doing Time Taught Him the Rules Nobody Else Would - Big Herc

   Ep. 12 Doing Time Taught Him the Rules Nobody Else Would - Big Herc Marcus "Big Herc" Timmons was a straight-A student and a standout athlete growing up in Sacramento, the kind of kid nobody expects to end up behind bars. A wrong turn into gang life and drug dealing sent him through the California Youth Authority as a teenager, and before the bank robbery that would put him behind bars for almost a decade, he even worked as a performer in the adult film industry, just one more chapter of a resume nobody would guess leads to a media company. Nobody hands you a manual for surviving prison, and getting it wrong can get you killed. Herc had to write his own rulebook in real time, and that rulebook became the foundation for everything he built after he walked out. Herc turned that hard-won knowledge into Fresh Out: Life After the Penitentiary, a YouTube series and media company built to do what nobody did for him: tell the truth about prison and life after release, without the Hollywood gloss. Between the flagship show, the Prison Talk podcast and miniseries, guest interviews, and the Back On Your Feet program supporting formerly incarcerated musicians and artists, Fresh Out has grown into a real business built entirely on lived experience, down to a commissary store where merch sales fund new content. Herc doesn't sand down the hard parts. He talks candidly about the violence, the isolation, and the grind of rebuilding a life with a felony record, while handing over the practical, sometimes life-or-death knowledge that keeps first-timers safe on the inside. His story is proof that the education nobody would choose can still become the foundation for a business, and a mission, that saves lives. Connect with Big Herc: Website > https://www.freshoutseries.com YouTube > https://www.youtube.com/channel/UCTsGL6oeAKi4lHIMfWwkcyA Instagram > https://instagram.com/freshoutseries Facebook > http://www.facebook.com/freshoutseries Twitter > http://www.twitter.com/freshoutseries More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

8. 

   27 Aug 2026

   The Pharma Rep Who Started Treating Burnout With Dinner Parties. - Britta Kramer

   Ep. 11 The Pharma Rep Who Started Treating Burnout With Dinner Parties. - Britta Kramer Britta Kramer's earliest memory of food is in her grandmother Anna's kitchen in Austria, where a meal was never just a meal - it was an expression of care, beauty, and connection. That imprint stayed with her through a career in pharmaceuticals, until a 2006 stint assisting the Food & Wine team at Napa Valley's Festival del Sole put her in the room with world-renowned chefs and changed everything. She left pharma soon after, spent four months traveling through 15 countries, and let food, culture, and community become her teachers. In 2007 she founded Private Palate, and within a year was cooking for professional athletes in Milwaukee - work that expanded over time to clients across the MLB, NBA, NHL, and PGA, along with private celebrity clients. A move to New York in 2012 led her to the International Culinary Institute and a decade spent curating full-sensory private events - food, florals, styling, direction - while building and managing a team of chefs across multiple states. A 2016 stretch living in Bali, steeped in meditation and plant-forward cooking, gave her "From Root to Blossom," her philosophy of using every part of the vegetable to cut waste and maximize nourishment. Then the pandemic changed the assignment: watching people navigate anxiety and burnout with no real tools around food, Britta shifted from private, elevated experiences to global workplace wellbeing education, eventually building The Mood Food Method, a four-week program bringing her approach directly into people's homes. Britta's throughline, whether she's plating for an all-star athlete or teaching a burned-out team how to cook again, is simple: nourishment only works if it fits into real life. Connect with Britta: Website > https://www.privatepalate.com/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

9. 

   20 Aug 2026

   He Didn't Have the Skills to Run a Business, Just the Nerve. - Mike Konrad

   Ep. 10 Bad at Assessing Risk, Great at Starting a Company: Mike Konrad Mike Konrad never set out to be an entrepreneur. In 1992, he founded Aqueous Technologies, an equipment manufacturer for the electronics assembly industry, not because he had a business plan but because he had designed a product he believed in and couldn't convince his employer to build it. The only path left was to build it himself. He walked into that decision with strong technical skills but zero formal business training, and with a set of traits that would sound like liabilities on any resume: ego, passion, arrogance, ignorance, and a genuinely poor ability to assess risk. Ironically, those are exactly the traits that got him off the ground. Ignorance can be bliss, and bliss is sometimes what it takes to leap. But the same qualities that launched the company nearly took it down. Mike had to recognize that his early recklessness carried real limits, then rebuild himself around business acumen, disciplined strategy, and sustainable leadership instead of raw enthusiasm. That transformation extended into how he thought about marketing itself. He started out with the chest-thumping, hype-driven advertising typical of his industry, but came to reject it in favor of what he calls conscious marketing: building authority through genuine value instead of empty claims, an approach he's found resonates especially with younger decision-makers who want substance over noise. Today he splits his time between technical circles, lecturing on electronics reliability at industry conferences, and academic ones, speaking candidly to engineering students about the realities of starting a business. He's also written The Reluctant Entrepreneur: Anatomy of a Business Startup, From Uncertainty to Unstoppable. Mike's story is proof that the instincts which make someone reckless enough to start a company are rarely the same instincts that let them keep it alive. Connect with Mike > https://www.mikekonrad.com/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

10. 

    13 Aug 2026

    Built for the Job by the Last Place You'd Expect - Eric Robinson

    Ep. 9 Built for the Job by the Last Place You'd Expect: Eric Robinson Eric Robinson's path to the FBI began somewhere no one expects: ministry. The principles he learned there didn't get left behind when he became a Special Agent. They became the foundation he leaned on through 15 years as a SWAT operator, tactical and firearms instructor, and investigator working Human Intelligence and National Security cases. It's an unlikely combination: a man grounded in spiritual formation, operating in a world of informants, terrorists, and exploited teenagers. But that grounding is exactly what let him thrive where the job breaks most people. Two of Eric's cases earned the Attorney General's Award, though the recognition isn't really the point of his story. The point is how someone finds the resilience to sit across from a terrorist in an interrogation room, or confront the reality of trafficked teenagers, and still hold onto their humanity. Eric talks candidly about both sides of that work: the grit and the darkness, and the human and spiritual core that kept him steady through it. He also brings a rare, ground-level perspective on how law enforcement actually engages with subjects, cutting through a lot of what gets lost in today's headlines. His story is proof that the most unlikely preparation for a career can turn out to be the most important. Connect with Eric:I think Website > https://www.preachertobreacher.com/ Instagram > https://www.instagram.com/_eric_robinson/ LinkedIn > https://www.linkedin.com/in/eric-robinson-9220053a4/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

11. 

    6 Aug 2026

    No Three Strikes: Jack Oujo on Money, Baseball, and Second Chances - Jack Oujo

    Ep. 8 No Three Strikes: Jack Oujo on Money, Baseball, and Second Chances - Jack Oujo At 30, Jack Oujo was broke, watching his professional baseball dream end, and about to become a father. Most people would have called that rock bottom. Jack calls it the foundation of everything that came after. In this episode, Jack — founder of Oujo Wealth Strategies, now one of the largest tax-focused wealth management firms in the country — walks through how he rebuilt his life and career from nothing using discipline, relentless self-education, and a philosophy he now teaches to everyone he works with: always have a Plan B. He explains why consistent processes beat lofty goals every time, and why trust and customer service, not returns alone, are what actually build a business that lasts. Before wealth management, Jack spent eight years as a professional baseball umpire, and it's there he picked up the line that anchors his approach to money: unlike ballplayers, most people don't get three strikes when it comes to their finances. This conversation is about what changes when you treat every financial decision like it might be your last shot. Connect with Jack Oujo: Website > http://www.toosmarttobeanumpire.com/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

12. 

    30 Jul 2026

    His Leap of Faith Landed Him in a Distillery. - Matt Estrin

    Ep. 8 His Leap of Faith Landed Him in a Distillery. - Matt Estrin Matt Estrin spent 15 years on staff at churches across Colorado, most recently as worship pastor at Journey Christian Church in Greeley, before he ever thought about running a business. The distilling started as nothing more than an experiment in his garage, a way to unwind after a career built around walking other people through their hardest days. He had no exit plan from the ministry and no business background. When the garage hobby got serious, Matt enrolled at Moonshine University in Kentucky to learn the craft properly, then opened 477 Distilling in downtown Greeley in 2019, named for the 477 votes that ended the city's decades-long prohibition in 1969. A single tasting room grew into two locations, with a second following in nearby Loveland, and Matt kept saying yes to the next idea. He co-owns Greeley Hatchet House, an axe-throwing venue that opened in the middle of the pandemic, runs After Hours Cocktail Bar in Fort Morgan, and launched Oak and Maple, a waffle and boozy-brunch concept that marked his first foray into running a restaurant. By his own count, seven businesses in seven years, each one built on the same instinct that got him into a garage full of stills in the first place. Somewhere in the middle of running all of it, Matt decided to write a book. He is dyslexic, which made the process far harder than it sounds, but he wrote I Know the Owner: From Holy Water to Happy Hour himself anyway, documenting the sleepless nights, the ventures that did not work, and the stretch where a global pandemic threatened to take down everything he had built. Matt's story pushes back on the idea that a calling and a career have to be permanent, or that changing direction later in life means starting from zero. He took what 15 years of leading a congregation had taught him, patience, people skills, the ability to sit with someone else's hard day, and pointed all of it at a completely different kind of business. It is a reminder that the skills that make someone good at one thing rarely stay confined to it. Connect with Matt Estrin: Website > https://www.mattestrin.net Instagram > https://www.instagram.com/mattestrin/ LinkedIn > https://www.linkedin.com/in/matt-estrin-223125113/ More from Unlikely Success: Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

13. 

    23 Jul 2026

    No Dirt. No Contacts. No Problem. - Chris Corkery

    Episode 7: No Dirt. No Contacts. No Problem. - Chris Corkery Chris Corkery had no farming background, no contacts in Milwaukee, and no soil. He built a farm anyway. Corkery's path started in marketing, then took a turn into professional kitchens as a chef in New York City. When he decided to build something of his own, he didn't look for open land. He looked for an empty industrial building in the middle of an inner-city food desert, on a brownfield site where a shuttered auto parts plant once stood, and moved to Milwaukee to build it, knowing no one there. That building became Hundred Acre: a hydroponic farm that grows leafy greens, herbs, and pesto indoors, year-round, without a single patch of dirt. What started as an experiment in a reclaimed factory has grown into shelf space at Kroger, Metro Market, Pick 'n Save, and Festival Foods locations across the state, along with partnerships feeding local schools and donations to Feeding America along the way. Corkery talks through the leap from chef to founder, what it took to convince a city to believe in a farm with no fields, and how a former industrial wasteland turned into a working farm feeding its own neighborhood. If you've ever assumed you needed the right connections, the right land, or the right background to build something real, Chris Corkery is proof that all you actually need is a building and the will to figure the rest out. Connect with Chris Corkery: Website > https://www.hundred-acre.org Instagram > https://www.instagram.com/hundredacre_mke/ YouTube > https://www.youtube.com/@hundredacre4177 LinkedIn > https://www.linkedin.com/company/hundred-acre-empowered-by-planet-to-plate/ Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

14. 

    16 Jul 2026

    He Asked for One Shark. He Got Three. - Tom Burden

    Episode 6: He Asked for One Shark. He Got Three. - Tom Burden Tom Burden spent his time in the Air Force keeping F-16s in the air, not building consumer products. But it was exactly that work, wrestling tools across the curved, awkward surfaces of a fighter jet, that led him to invent Grypmat, a flexible, non-slip mat that keeps tools locked in place no matter the angle. He built the first versions in his own garage, funded early production through Kickstarter, and eventually landed a spot on Shark Tank. Burden walked in seeking $200,000 for 10% of his company. He walked out with something rarer: a combined offer of $360,000 for 30% equity, split between three sharks, Mark Cuban, Lori Greiner, and Sir Richard Branson, all at once. In this episode, Tom talks about the years of grinding it out in a home workshop before that appearance, the sales realities of going from a single garage operation to a nationally recognized product, and what it actually took to get three sharks in the tank to agree to team up instead of compete for one guy's tool mat. If you've ever wondered what it takes to turn a workplace annoyance into a business several sharks wanted a piece of, this is that story. Connect with Tom Burden: Website > https://www.grypmat.com (https://www.grypmat.com) LinkedIn > https://www.linkedin.com/in/toburden Know someone who would be perfect for the show or want to reach out? > https://unlikelysuccesspodcast.com

15. 

    9 Jul 2026

    Going with He Started as a Clown. He Built an Empire. - James Sinclair

    Episode 5: He Started as a Clown. He Built an Empire. - James Sinclair Most business empires don't start with face paint and balloon animals. James Sinclair's did. In this episode, James traces a career that began as a children's entertainer and grew into one of the most deliberately integrated business portfolios you'll find anywhere. Real estate holdings, children's entertainment attractions, Rossi Ice Cream, food distribution, kids toys, ecommerce brands - these aren't random bets. They're a vertically integrated empire where each piece feeds the others, built by someone who saw connections where most people would have seen chaos. James talks about how he built it, what drives him, and the business philosophy behind a career that has defied every conventional expectation along the way. If you've ever been told your starting point was too small or too silly to matter, James Sinclair is proof that it isn't where you start - it's what you build from there. Connect with James Sinclair: Website > https://www.jamessinclair.net Instagram > https://www.instagram.com/jamessinclairentrepreneur YouTube >https://www.youtube.com/@JamesSinclairEntrepreneur LinkedIn > https://www.linkedin.com/in/jamessinclairpartyman/ Know somoene who would be perfect for the show or want to reach out? >https://unlikelysuccesspodcast.com

16. 

    2 Jul 2026

    Nobody Wanted Detroit. Nick Did. - Nick Sanborn

    Episode 4: Nobody Wanted Detroit. Nick Did. - Nick Sanborn Nick Sanborn didn't inherit a construction empire. He built one from scratch in a city that most people had already written off. In this episode, Nick talks about starting Sanborn Construction Group from zero in Detroit - a city with no shortage of opportunity if you're willing to do the work others aren't. While most contractors were looking elsewhere, Nick leaned in, taking on a high volume of construction, maintenance, and development projects in a market that rewards persistence over pedigree. We also get into something most construction business owners haven't figured out yet: social media as a legitimate marketing tool. With nearly 200,000 YouTube subscribers, Sanborn Construction Group has built an audience that most media companies would envy - and Nick talks about how that happened and what it means for the business. If you've ever thought about betting on a place or an idea that others have given up on, this conversation will resonate. Contact Nick on his Website > https://www.sanbornconstructiongroup.com Watch Nick on YouTube > https://www.youtube.com/@SanbornConstructionGroup Know of somone who would be a good guest or want to reach out? > https://unlikelysuccesspodcast.com

17. 

    18 Jun 2026

    He Built the Homes. Then He Started Selling Them - Richard Ruvin

    Episode 2: He Built the Homes. Then He Started Selling Them Before Richard "Rick" Ruvin's team was selling $200 million in Milwaukee real estate every year, he was a kid in a men's clothing store - impressing salesmen twice his age and not fully understanding why it came so naturally. In this episode, Rick traces a career path that most people couldn't have drawn in advance. From men's fashion to residential construction, from selling out condo developments to buying into one of Milwaukee's most recognized luxury real estate teams, his story is less about following a plan and more about recognizing what he was good at and leaning into it at every turn. We also get into the side of Rick that doesn't show up in the Wall Street Journal write-ups - his commitment to mentorship and giving back to the next generation of real estate professionals, and what drives that. Rick is the author of The Attractive Agent and a frequent speaker at national real estate conferences. If you've ever wondered what separates the top producers from everyone else, this conversation is a good place to start. Rick's Profile > https://www.thefrgteam.com/agent-profile/richard-ruvin-102264740 My Website > https://jeffreykoenig.com/ My LinkedIn > https://www.linkedin.com/in/jeffrey-koenig-36538887/ Reach Out or Join us on an Episode >https://unlikelysuccesspodcast.com

18. 

    11 Jun 2026

    My Story - From the Drive-Thru to the Business Empire - Jeffrey L. Koenig

    Episode 1: My Story - From the Drive-Thru to the Business Empire -Jeffrey L. Koenig Most people don't map out a path from fast food to owning a holding company. I certainly didn't. In this first episode, I share my own story - the unexpected detour that kept me in the service industry longer than I planned, the 2008 financial crisis that somehow became my opening, and the series of bets that grew from a single four-family building in Milwaukee into a group of companies spanning property management, construction, and facilities services. None of it was part of a plan. A lot of it came down to luck. But luck has a short shelf life if you don't know what to do with it - and that's really what this episode is about. This is the story behind Sigma Commercial and why I started Unlikely Success: because the straightest path to building something is rarely straight at all. My Website > https://JeffreyKoenig.com/ My Company > https://sigmacommercial.com/ LinkedIn > https://www.linkedin.com/in/jeffreylkoenig/ Want to be a Guest or Get in Touch? https://unlikelysuccesspodcast.com/

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