AmiSights: Financing the Future For Small Business Owners and Entrepreneurs

MultiFunding
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The weekly AmiSights Podcast will feature dynamic interviews with entrepreneurs, thought leaders, various industry CEOs, industry professionals, public speakers, and more about their unique insights, practices, and valuable life experiences. Join Ami Kassar, CEO of MultiFunding, and his humor on the show that can help you grow and transform your business.

  1. 3d ago

    236: 15+ Businesses Later: Lessons From the Startup He Lost

    On this episode of AmiSights, host Ami Kassar and co-host Lynn Ozer talk with Mark Winters, author of Rocket Fuel and Visionary. Mark has started, bought, sold, or shut down 15 businesses. His first was a cyber cafe in Milwaukee in the early days of the internet. It drew gamers, families, and local TV crews. Then one investor blocked new funding and the business had to close. Mark shares the pricing lessons from that first venture. He talks about the analytics companies he built and sold, including one acquired by Experian. He also explains why he now helps visionaries and integrators climb out of what he calls the pit. "You make the leap thinking, 'I'm going to make more money than I ever have. I'm going to have control over my time. I'm going to only work with people that I love. I'm going to make a huge difference in the world.' And then you find yourself six months into it, twelve months into it, and you're like, 'This is nothing like that. I've never worked more hours.'" Today's episode covers how Mark's first startup, a Milwaukee cyber cafe, took off and then closed when one investor blocked new funding. It also covers how he built and sold analytics companies, including one acquired by Experian. Mark then explains the visionary and integrator partnership behind Rocket Fuel, the book he wrote with Gino Wickman.   Connect with Mark: https://www.linkedin.com/in/markcwinters/ Head over to Mark's website: https://www.markcwinters.com/

    236: 15+ Businesses Later: Lessons From the Startup He Lost

  2. Oct 13

    235: The Loyalty Lane: Personalized Business Gifting That Builds Lasting Relationships

    On this episode of AmiSights, host Ami Kassar and co-host Lynn Ozer sit down with a very special guest. Charlotte Kassar is Ami's daughter and the founder of The Loyalty Lane, a corporate gifting and relationship management company she launched at 24. Charlotte shares why she decided to bet on herself and how she researches each recipient to create gifts people never forget. She talks about landing her first client, learning the business side of running a company, and why patience matters more than she expected. Ami opens up about trying not to be the overbearing entrepreneur dad and why he believes Charlotte's creativity will take her far. "Gifting is always something I've loved, and being able to turn your passion into your new job is the end goal. I wake up happy every day now and more inspired than ever. What this is all about is helping people feel unforgettable and making people feel understood." Today's episode covers how Charlotte launched The Loyalty Lane at 24 and why personalized gifts build real loyalty, getting the numbers right from day one and learning to wear every hat as a solo founder, and what Charlotte learned from watching her dad build MultiFunding. Connect with Charlotte: https://www.linkedin.com/in/charlotte-kassar-35147492/ Learn more about The Loyalty Lane: https://www.linkedin.com/company/the-loyalty-lane/home/ Recorded on 9/1/2026

  3. Sep 29

    234: How a Seattle Startup Is Fighting America's Home Ownership Gap

    Katrina Romatowski joins Ami Kassar and Lynn Ozer to talk about reSpace, her company making single family home ownership possible for about the cost of renting a one bedroom apartment. She explains how fractional co-living ownership works, why the listing service in her market won't touch her properties, and why retirees may be her biggest market. It's a sharp look at the housing affordability crisis and one entrepreneur's plan to fix it. "What reSpace does is we say, 'Hey, people are living this way. Now everybody gets a piece of the economic benefit. Everybody gets a piece of the pie.'" Today's episode covers how Katrina went from selling candy in middle school to building a real estate brokerage and a nonprofit, how the reSpace model gives co-living residents real ownership instead of rent, how financing, house rules, disputes, and resale work when you share a home, why the Northwest Multiple Listing Service won't list her properties and how she's going direct to buyers instead, why retirees who want to live with lifelong friends may be her strongest market, and her plan to expand up and down the West Coast in 2027. Connect with Katrina: https://www.linkedin.com/in/katrinaeileen/ Learn more about reSpace: https://www.respace.co/ Recorded on 7/2/26

    234: How a Seattle Startup Is Fighting America's Home Ownership Gap

  4. Sep 15

    233: The myEO Grit Unconference: What Happens When Entrepreneurs Build Their Own Agenda

    On this episode of AmiSights, my co-host Lynn Ozer and I welcome three guests from the first ever myEO Grit Unconference: Lauren Banyar Reich, Rachel Costello, and Tiffany Meyer. All three attended the event in Banning Mills, Georgia, where roughly sixty EO and EOA members built their own agenda, slept in treehouses, and learned from each other with no formal speakers and no cell service. Lauren, Rachel, and Tiffany share what drew them to the Unconference, the moments that stuck with them most, and how the community they built there has continued to shape their businesses and lives since. It is a candid conversation about what happens when entrepreneurs are given space, and nowhere to run to. "I too will survive and figure it out. And I have this amazing community of resources and people and knowledge and information right at my fingertips." — Lauren Banyar Reich Today's episode covers what the myEO Grit Unconference is and how it differs from a typical conference. We also discuss why removing Wi-Fi, agendas, and easy escape routes created deeper connection, and how grit circles help entrepreneurs support each other through real struggles. We get into the unexpected topics that came up, from AI to personal branding to divorce, and how the relationships built at the Unconference have continued to grow since. Want in on the next one? The myEO Grit Unconference returns December 8-11 in Banning Mills, Georgia. Click here to learn more! Connect with Lauren Banyar Reich: https://www.linkedin.com/in/lbrpr/ Connect with Rachel Costello: https://www.linkedin.com/in/rachelacostello/ Connect with Tiffany Meyer: https://www.linkedin.com/in/tiffany-meyer-37154b39/ Recorded on 8/20/26

    233: The myEO Grit Unconference: What Happens When Entrepreneurs Build Their Own Agenda

  5. Aug 25

    232: From Accidental Web Guy to Helping the Next Generation of Founders

    On this episode of AmiSights, host Ami Kassar and co-host Lynn Ozer talk with Christopher Thierry, CEO of LiquidDocs. Chris shares his path from a 21 year old web developer during the early dot com days to founder of Cimpl, a telecom expense management company he built and sold in August 2019. He talks candidly about missing his first fundraise, pivoting through two recessions, and the emotional toll of handing his company off to new owners. The conversation turns to what Chris is building now, including LiquidDocs and LensPlus, and why he believes AI has leveled the playing field for entrepreneurs willing to put in the work.   "When you don't raise the money you think you're going to raise, it forces a lot of things on you. You realize you can't just rely on optimism — you have to go out, sell, and make the business real." Tune in as Chris shares how he pivoted from a missed fundraise into a bootstrapped web consulting business. He also talks about building and selling Simple, his telecom expense management company, in August 2019. Recorded on 6/26/26

    232: From Accidental Web Guy to Helping the Next Generation of Founders

  6. Aug 25

    232: From Accidental Web Guy to Helping the Next Generation of Founders

    On this episode of AmiSights, host Ami Kassar and co-host Lynn Ozer talk with Christopher Thierry, CEO of LiquidDocs. Chris shares his path from a 21 year old web developer during the early dot com days to founder of Simple, a telecom expense management company he built and sold in August 2019. He talks candidly about missing his first fundraise, pivoting through two recessions, and the emotional toll of handing his company off to new owners. The conversation turns to what Chris is building now, including LiquidDocs and LensPlus, and why he believes AI has leveled the playing field for entrepreneurs willing to put in the work.   "When you don't raise the money you think you're going to raise, it forces a lot of things on you. You realize you can't just rely on optimism — you have to go out, sell, and make the business real." Tune in as Chris shares how he pivoted from a missed fundraise into a bootstrapped web consulting business. He also talks about building and selling Simple, his telecom expense management company, in August 2019. Recorded on 6/26/26

    232: From Accidental Web Guy to Helping the Next Generation of Founders

  7. Aug 11

    231: The Hidden Risk of Insuring Your Business the Wrong Way

    Ami Kassar and Lynn Ozer welcome Ulyanna Chung to AmiSights. Ulyanna owns franchise insurance agencies out of Las Vegas, Nevada, serving clients across five states. Before insurance, she spent six years in federal law enforcement, including two years as an air marshal, where she met her husband. Twenty-three years and a seven-year run in EO later, Ulyanna opens up about building her agency, preparing for AI to disrupt her industry, and what she's learned about success now that her sons are grown. "I would do one bit of wisdom: just love yourself. Do what's in your heart. If your heart is calling you to rule the world, then you do it — you do what you are meant to do on this earth, but make sure that's what you truly want and what's in your heart." Today's Episode Covers Going from federal air marshal to insurance agency owner Why AI is set to automate personal lines insurance, and how Ulyanna is pivoting toward commercial and financial services Redefining success and identity as an entrepreneur heading into a new life stage Recorded on 6/16/26

    231: The Hidden Risk of Insuring Your Business the Wrong Way

  8. Jul 28

    230: How a Family Business Became a Masterclass in Business Turnarounds

    In this week's edition of the AmiSights Podcast, we have James Perly joining Ami and Lynn for a wide-ranging conversation about entrepreneurship, resilience, and the lessons that come from building — and rebuilding — a business from the ground up. James grew up in a third-generation family map-making business in Toronto, one so well known that customers would ask for "a Pearly" instead of a map book by name. When his father passed away suddenly, James took over the company at just 21 years old, inheriting a business with debt nearly equal to its revenue and years of unresolved litigation. "The most valuable business skills are often the ones least taught in traditional education — like resilience, improvisation, and the ability to navigate ambiguity." The conversation covers three main threads: James's six-year restructuring of his family's map business and the eventual sale that gave him a fresh start; his pivot into building a company that helps Canadian tech firms secure government grants and tax credits, giving him a unique, decades-long view into what actually separates innovative businesses from the rest; and his candid reflections on navigating an extremely difficult personal chapter over the last several years, including a serious health crisis, and what he's learned about identity, resilience, and starting over. Along the way, James shares some of his favorite contrarian business insights, including a fascinating story about Warren Buffett and an unconventional business leader he once called irreplaceable. Recorded on 6/9/26

    230: How a Family Business Became a Masterclass in Business Turnarounds
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The weekly AmiSights Podcast will feature dynamic interviews with entrepreneurs, thought leaders, various industry CEOs, industry professionals, public speakers, and more about their unique insights, practices, and valuable life experiences. Join Ami Kassar, CEO of MultiFunding, and his humor on the show that can help you grow and transform your business.

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