Shows
How Did We Get Here?33. From Importing Lumber to Guiding Lives with Matt HobsonMatt Hobson's career journey feels like a cross-country hike. He went from studying spotted owls in Oregon's forests to importing lumber from New Zealand, and ended up helping people with their financial decisions.He is the ninth child of thirteen siblings. Yes, you read that right, thirteen! They didn’t call themselves "the wilderness" of Eastern Oregon for nothing. That ninth kid was shy in his youth, but soon discovered he had a special talent for connecting with people and making friends that would be useful later…When the 2008 financial crisis demolished his lumber import busi...2025-06-1937 minHow Did We Get Here?32. From Mania to Meaning with Phil PearlmanMeet Phil Pearlman, a former special education teacher with a trading background. He is now dedicated to helping people improve their health to boost their business and life results. In this conversation, he goes from explaining the current bird flu cycle and how it affects egg prices to a mindful parenting masterclass, and believe it or not, he ties it all back to health.Irreverent, politically incorrect, and fun, Phil teaches with his own example how intentional habits and wise choices can transform a life for the better. Join us for the advice, stay for the laughs!2025-06-0541 minHow Did We Get Here?31. From Therapy Couch to Financial Advisor Coach with Ashley QuammeAshley Quamme's path in financial advice was not the most typical one, but there were some early signs, like the fact that she was born on “Tax Day” and used to offer counseling to her classmates in the lunch line. Later, she worked as a mental health therapist until she discovered a new way to use her skills: advising advisors. If we add that she is married to a CFA and is the daughter of a CPA, now it makes way more sense.Let’s dive into Ashley’s journey and see how a psychological background and a lot of...2025-05-2237 minHow Did We Get Here?30. From Marketing Noise to Meaningful Work with Dennis Moseley-WilliamsWhat if the real reason people hire you has nothing to do with money?In this conversation, keynote speaker Dennis Moseley-Williams shares how his background in anthropology shaped a completely different approach to financial advising and business building. He explains why clients crave fulfillment, connection, and transformation more than they care about financial metrics.For Dennis, rejecting traditional business models, focusing on fairness, and creating memorable client experiences has helped him build a practice people want to be part of. He also shares why we are now living in a transformation economy, where doing work...2025-05-0844 minHow Did We Get Here?29. From Sushi Entrepreneur to Financial Advisor with John StojJohn Stoj’s career took some unexpected turns—Wall Street trader, sushi entrepreneur, and reluctantly, a financial advisor. Along the way, he realized he loved helping people with money, just not in the way big firms do it.This may just be the least straight-line journey we’ve gone through yet! Stay tuned as we get into John’s story, where he “kicked and screamed” his way into a rewarding career.Connect with us!John Stoj on LinkedInVerbatim FinancialJess Bost on LinkedInLake Avenue FinancialMark Ne...2025-04-2439 minHow Did We Get Here?28. From Lacrosse to Cross-Border Finance: Building Bird’s Eye with Sam RookIn this episode, Mark and Jess talk to Sam Rook, a Canadian financial advisor who went from studying physical education to becoming a go-to expert in cross-border and founder of Bird’s Eye Wealth. How did that happen? A $10,000 investment, and an inspiring mentor who changed his path forever.In this episode:- Sam’s career switch from teaching to wealth management - Why he left a big firm to start his own business - What U.S. advisors must know about Canadian clients- Why hiring outside the indust...2025-04-1036 minHow Did We Get Here?27. From College Dropout to Grief Guru with Kathi BalasekKathi Balasek shares her remarkable journey from flunking college, becoming a physical education teacher and then eventually, a grief expert. Kathi demonstrates how seemingly unrelated skills create a unique path for helping others navigate loss.Key Takeaways:• Grief is not a competition – "the only loss that matters is your loss"• Focusing on emotions rather than comparing experiences creates connection• How financial professionals can support grieving clientsWhether you're navigating personal grief or supporting someone through loss, this conversation offers practical wisdom for showing up when life gets messy.Connec...2025-03-2740 minHow Did We Get Here?26. How Did We Get From Rock ‘n’ Roll to Financial Planning? Part 2 with Matt ZeiglerMatt Zeigler’s journey shows the power of curiosity and adaptability in navigating one's career through uncertainties. From his unexpected pivots during the global financial crisis to initiating his podcast "Just Press Record," Matt emphasizes the importance of embracing chaos as a path to growth.Key takeaways:• Resilience during the global financial crisis• Turning career challenges into opportunities• The power of curiosity• The value of non-traditional networkingConnect with us!Matt Zeigler on LinkedInSunpointe InvestmentsCultish CreativeJess...2025-03-1328 minHow Did We Get Here?25. How Did We Get From Rock ‘n’ Roll to Financial Planning? with Matt ZeiglerMatt Zeigler started out as a guitarist, hustling to make it in the music industry. Then, the dawn of the internet sent him along a different path, to financial services. He talks about how he was able to see his ADHD as a strength, and inspires listeners to embrace setbacks and not be afraid to pivot towards finding their passions.Key Takeaways:• Matt's transition from music to finance• Happiness in the workplace as a catalyst for change• Overcoming career setbacks and rejections• Harnessing ADHD as a unique strength• Less...2025-02-2729 minHow Did We Get Here?24. How Did We Get From Manufacturing to Financial Planning? with Cris WallaceCris Wallace shares his remarkable journey from being a plant manager to becoming a dedicated financial planner. We discuss his motivations, the challenges he faced, and how relationships and understanding emotions around money can lead to success in financial advising.Key Takeaways:• Cris’s shift from plant management to financial planning• The inspiration behind helping others financially• Challenges and fulfillment in making career transitions• Importance of relationships and trust in financial advising• Addressing retirement fears and spending strategiesConnect with us!Cris Walla...2025-02-1337 minHow Did We Get Here?23. How Did We Get From UConn Track to Index Funds? with Justin CarbonneauJustin Carbonneau’s journey from track and field to military service to the world of finance is a powerful example of turning challenges into opportunities. Justin has had to navigate tough transitions, from a demanding New York City internship to managing financial crises. Whether it’s finding encouragement online or the power of teamwork, his story shows how resilience and the right relationships can shape a rewarding career path. Connect with us!Justin Carbonneau on LinkedInValideaValidea Capital ManagementJustin’s BlogJess Bost on LinkedInLa...2025-01-1648 minHow Did We Get Here?22. How Did We Get From Wall Street to CEO? with Ryan KruegerIn this episode, we chat with Ryan Krueger about how discomfort can lead to real growth. Ryan shares his thoughts on staying positive, finding joy in your work, and creating success that aligns with your values. We also talk about how challenges can teach us important lessons and why discomfort is often the key to becoming stronger and more resilient. It's a warm and inspiring conversation filled with practical insights for navigating life and work.Connect with us!Ryan Krueger on LinkedInRyan Krueger on XFreedom Day Solutions...2025-01-0940 minHow Did We Get Here?21. How Did We Get From Advisor to Mentor? with Julie JohnsonToday we chat with Julie Johnson, a financial advisor turned mentor, as she shares her journey of helping families and advisors navigate the challenges of wealth transfer. Julie blends empathy and expertise, shaped by her own personal experiences, in a fresh perspective to managing finances across generations.We also explore the growing role of women in finance, the importance of mental health, and the concept of "funded contentment"—a balance between financial security and living a fulfilled life. Connect with us!Julie Johnson on LinkedInXY CommunicationJess Bost on...2024-12-3148 minHow Did We Get Here?20. How Did We Get From Theology to Financial Planning? with Morgan RanstromWhat makes someone trade academia for financial advising during a recession? In this episode, we sit down with Morgan Ranstrom as he takes us through his remarkable journey from theology to finance. Combining technical skills with a deep understanding of human behavior, Morgan proves that financial planning is about more than numbers—it’s about people.From navigating life transitions to balancing risk and reward, Morgan shares insights that go beyond investments, inspiring advisors and clients alike.Connect with us!Morgan Ranstrom on LinkedInTrailhead PlannersJess Bost on Link...2024-12-1957 minHow Did We Get Here?19. How Did We Get From Baghdad to Entrepreneur? with Van SmithImagine starting a law firm with just a laptop and an iPhone. That’s exactly what Van Smith did! In this episode, Van shares how he grew his Virginia-based firm from scratch into a team of 30. His background wasn’t entrepreneurial at all, but after tackling challenges like undergrad during 9/11, a stint in Baghdad, and the 2008 financial crisis after law school—Van dug in and simply got to work. In this episode we talk about:Turning life’s chaos into growth.Smart financial habits that build long-term success.The power of starting small and staying consistent.Whether...2024-12-1242 minHow Did We Get Here?18. How Did We Get From a Childhood Goal to Estate Law? with Jenny RozelleJoin us as we chat with Jenny Rozelle, an estate and elder law expert who brings a down-to-earth approach to legal planning. From her small-town beginnings to leading a successful law firm, Jenny shares how hard work and community-focus drive her success. She breaks down why estate planning matters for everyone, and gives simple, practical advice to protect what you value most.Connect with us!Jennifer Rozelle on LinkedInIndiana Estate and Elder LawJess Bost on LinkedInLake Avenue FinancialMark Newfield on LinkedIn...2024-12-0539 minHow Did We Get Here?17. How Did We Get From Failed Classes to Fitness in Finance? with Aravind SithamparapillaiIn this episode Aravind Sithamparapillai shares his journey, facing family expectations and self-doubt as he built a career in finance. Aravind opens up about overcoming struggles, including mental health challenges, and finding his way back to university. His story shows the power of self-belief, resilience, and the importance of doing what you actually care about. Join us for a story of growth, courage, and finding purpose beyond money.Connect with us!Aravind SithamparapillaiIronwood Wealth ManagementJess Bost on LinkedInLake Avenue FinancialMark Newfield on LinkedIn2024-11-2843 minHow Did We Get Here?16. How Did We Get From History Major to Financial Advisor? with Dennis MortonMeet Dennis Morton—a former history major, band musician, and missile operator who’s now the founder of a financial advisory firm. In this episode, Dennis talks about his winding career path from military life to finance, and shares his hard-earned lessons and stories. Learn how he found his true calling, built a new career from scratch, and used his background in empathy and communication to connect with clients. It's a story of big career changes, family support, and finding purpose.Connect with us!Dennis Morton on LinkedInMorton Brown Family WealthJe...2024-11-1446 minHow Did We Get Here?15. How Did We Get From Answering Phones to Index Funds? with Perth TolleIn this episode, we chat with Perth Tolle, a finance trailblazer who mixes personal values with smart investing. From her time as a Fidelity advisor to creating a freedom-focused index for emerging markets, Perth’s journey shows how staying true to your beliefs can lead to success. We also talk about taking risks, changing careers, and how community support can help you bounce back from challenges. Listen for tips on investing, new markets, and the power of connections.Connect with us! Perth Tolle on LinkedInLife + Liberty IndexesJess Bost on Lin...2024-11-071h 04How Did We Get Here?14. How Did We Get From Investment Banker to Artist? with Dave RossJoin us as Dave Ross shares his unique journey from asset management to transportation executive to artist. He talks about chasing impact over following a set career path, the value of self-awareness, and learning from mentors. We also dive into career transitions, personal growth, and lessons from 2020 on finding clarity and building strong relationships. This episode offers practical tips to help you align your career with who you want to become.Connect with us! Dave’s ArtDave’s SubstackJess Bost on LinkedInLake Avenue FinancialMark...2024-10-3151 minHow Did We Get Here?13. How Did We Get From Pageant Queen to Queen of Alts? with Shana Orczyk SisselJoin us as Shana Orczyk Sissel, founder of Banríon Capital, shares her journey into finance without a traditional finance degree. From her experiences in sports, theater and pageants to overcoming ADD and navigating challenges in a demanding industry, Shana’s story highlights resilience and creativity. She talks about building her business and balancing life as a single mom, offering valuable insights for anyone looking to succeed in finance and beyond.Connect with us! Shana Orczyk Sissel on LinkedInBanríon Capital ManagementJess Bost on LinkedInMark Newfield on Li...2024-10-241h 09How Did We Get Here?12. How Did We Get From Astrophysics to Editor-in-Chief? with Lara CriggerIn this episode, Lara Crigger talks about her journey from studying astrophysics to becoming a writer and working in commodities and ETFs. She shares how she followed her passion for storytelling, turned down scholarships, and balanced a busy career with motherhood. Lara also talks about overcoming challenges like burnout and grief, rescuing her dog after Hurricane Katrina, and the lessons she’s learned about leadership and building strong teams. Her story is full of inspiring career advice!Connect with us! Lara Crigger on LinkedInShoe Leather by Lara CriggerJess Bost on...2024-10-1752 minHow Did We Get Here?11. How Did We Get From Internet Newbie to Nitrogen? with Aaron KleinAaron Klein’s childhood struggles with money and near foreclosure shaped his approach to risk and opportunity in his career. Despite early failures, he founded Riskalyze (now Nitrogen), a company that revolutionized financial advising by creating a way to measure risk with a "risk number." Through his story, Aaron touches on resilience, timing, and innovation, as well as the challenges of leading through tough times like the COVID-19 pandemic. He also reflects on taking time off for family, finding balance, and the emotional side of risk in both investing and life.Connect with us! Aaron Kle...2024-10-101h 16How Did We Get Here?10. How Did We Get From Dishwasher to CFA®? with Derek HagenIn this episode, we share the inspiring story of Derek Hagen, who overcame poverty and started working at a young age to eventually become a successful financial advisor. Derek’s journey shows how hard work, education, and perseverance can change your life. He talks about finding his passion for finance, navigating career choices after college, and balancing full-time work with further education. Derek also highlights the importance of using wealth to improve life rather than as a goal itself. It’s a powerful conversation about resilience, smart decisions, and finding purpose in your work.Connect with us! ...2024-10-031h 00How Did We Get Here?9. How Did We Get From Farm School to Financial Planner? with Cullen RocheIn this episode of “How Did We Get Here?”, Cullen Roche shares his journey from a unique childhood to becoming a leader in finance. Raised on a farm in Washington, DC, Cullen’s large family helped shape his independent yet team-oriented mindset.Cullen discusses how his wife’s influence guided him from stock picking to financial planning, and how moving to California became a pivotal turning point in his career. He also dives into the significance of macroeconomics in personal investing, key lessons from the 2008 financial crisis, and the value of patience and resilience when managing finances.Con...2024-09-261h 20How Did We Get Here?8. How Did We Get From Concert Promoter to CFP®? with Nick GertsemaIn this episode, we explore how unexpected career twists can lead to fulfilling paths. Nick Gertsema shares his journey from concert promoter to financial advisor, showing how embracing change can open new opportunities. We also discuss the story of a father and son who took unconventional career routes, offering lessons in resilience and finding one's true calling.The episode dives into investing tips from legends like Warren Buffett and George Soros, stressing the importance of staying disciplined in unpredictable markets. We cover strategies like tax loss harvesting, managing emotions in finance, and the value of seeking professional...2024-09-1947 minHow Did We Get Here?7. How Did We Get From Paperboy to Wall Street? with Bob SeawrightIn this episode, we talk with Bob Seawright, who went from being a paperboy in his hometown to becoming a Chief Investment Officer and a well-known writer. Bob shares how his early jobs, like delivering newspapers in the cold and umpiring baseball games at 14, taught him important lessons that shaped his career. He also opens up about his journey from an unsatisfying legal career to finding his true passion on Wall Street. Filled with stories, wisdom, and practical advice, this episode is perfect for anyone looking for inspiration on how to follow their dreams and stay true to their...2024-09-1247 minHow Did We Get Here?6. How Did We Get from Gender Bias to Thriving in Finance? with Arlene MossIn this episode, we talk with Arlene Moss about her 30-year journey in the financial world. Arlene shares how she stayed true to herself, even in an industry that often pushes people to fit in. Starting on Wall Street in the early 2000’s, Arlene faced challenges like gender bias but used these experiences to grow and change. She also discusses balancing work with family and the importance of mentors. This episode is filled with personal stories and practical advice for anyone looking to stay authentic in their career.Connect with us! Arlene Moss on LinkedInJess Bost on...2024-09-0538 minHow Did We Get Here?5. How Did We Get From Furniture Mart to Finance? with Stoy HallWhat if everything you know about money is wrong? Join us as Stoy Hall, the founder of Black Mammoth and host of the NoBS Wealth podcast, shares his story—from growing up with a hardworking single mom to delivering appliances. Stoy's experiences teach us what real wealth means. We also explore four common money mindsets and how they shape your financial decisions. This episode will help you rethink your relationship with money and show you how to aim for true financial freedom and happiness.Connect with us! Jess Bost on LinkedInMark Newfield on...2024-08-2937 minHow Did We Get Here?4. How Did We Get From Proofreading to Morningstar? with Christine BenzIn this episode of "How Did We Get Here?", we chat with Christine Benz, an expert in retirement and investment planning. Christine shares her unique career journey, starting from proofreading medical journals to building a long career at Morningstar. We explore how her dedication and curiosity led her from being a copy editor to a mutual fund analyst, and eventually, to managing a team.Christine also talks about how career changes can affect retirement savings and the importance of financial planning during these transitions. We discuss how different life experiences shape our financial decisions and why there's...2024-08-2250 minHow Did We Get Here?3. How Did We Get From IT to Finance? with Meg BarteltIn this episode, we sit down with Meg Bartelt, a financial planner with a background in tech writing, to talk about smart money moves for your 20s, 30s, and 40s. Meg shares her personal journey, from working in IT during the dot-com boom to helping people navigate their finances today. She explains why your habits and emotions often matter more than math when it comes to money and offers tips for adjusting your financial plan as your life changes—like when you switch careers, start a family, or face unexpected challenges.We also explore how even high ea...2024-08-1543 minHow Did We Get Here?2. How Did We Get from Film to Finance? with Dave NadigEver wondered what it takes to make a big career shift or take a life-changing sabbatical? In this episode, we chat with Dave Nadig, who shares his journey from Hollywood screenwriter to finance professional.Dave talks about pursuing an MBA and diving into finance, showing how understanding money and embracing the unknown can lead to unexpected, fulfilling careers. We explore how curiosity, inspired by Richard Feynman’s advice, and facing fears, like those after 9/11, shape our professional lives.We also cover the practical side of taking a career break, focusing on financial planning for sabbaticals. Di...2024-08-0829 minHow Did We Get Here?1. How Did We Get Here?Ever wonder how a college dropout becomes a top financial advisor? In the very first episode of "How Did We Get Here?," hosts Jess Bost and Mark Newfield share their own remarkable career journeys. From Mark's days under the hood of cars to his rise in finance, you'll find inspiration in their stories. Jess adds a heartwarming touch with an anecdote about her daughter's long-distance relationship, highlighting life's unpredictable connections.We dive into the blend of luck and planning that brought this podcast to life, offering key financial insights and practical advice from sabbaticals to retirement. Jess...2024-08-0119 min
The Breakthrough Factor with Jess BostA Relentless Pursuit of Better with Mark Newfield Pt. 2Two things are given to you without your choice: your family and your biology. These things do not have to define you...but they CAN inform you. In this episode, Mark and I talk about how his formative years and his ADHD diagnosis could have (and maybe should have) put him on a path toward destruction. Instead, with the generosity and care of a few people early in life, he chose to make one small change every day and relentlessly pursued better. Get to Know Mark:Mark started his professional work life as a consultant w...2022-06-2340 minThe Breakthrough Factor with Jess BostA Relentless Pursuit of Better with Mark Newfield Pt 1Two things are given to you without your choice: your family and your biology. These things do not have to define you...but they CAN inform you. In this episode, Mark and I talk about how his formative years and his ADHD diagnosis could have (and maybe should have) put him on a path toward destruction. Instead, with the generosity and care of a few people early in life, he chose to make one small change every day and relentlessly pursued better. Get to Know Mark:Mark started his professional work life as a consultant...2022-06-2337 min