Small Business Big Deal Podcast

This week on Small Business Big Deal, Tracy sits down with Elliott Orsillo, co-founder of Season Investments, to explore what it really means to build a business rooted in integrity, curiosity, and long-term thinking. Elliott's journey from engineering at Stanford to leading a wealth management firm is filled with valuable lessons about resilience, partnership, and trust. He shares how a foundation in problem-solving and risk analysis shaped his approach to investing — and how staying curious has kept his business innovating and his clients grounded through market volatility. In this episode, Tracy and Elliott talk candidly about: The evolution from corporate life to entrepreneurship — and why he traded a Fortune 500 career for building something of his own. What curiosity looks like in practice and how it drives better decision-making and business growth. The toughest season of his entrepreneurial journey: uncovering client fraud, rebuilding trust, and repaying investors out of sheer integrity. The importance of mutual respect in partnerships and why theirs has lasted more than 14 years. How parenting three teenage daughters has shaped his leadership style and emotional intelligence. Why maintaining balance isn't about working less — it's about knowing what really matters. His take on AI's growing role in wealth management and why human connection will always matter more than automation. Elliott also shares his favorite outdoor escape in Colorado, the two books that changed how he views control (The Untethered Soul and Letting Go), and even his hidden talent that drives his daughters crazy. If you've ever wondered how curiosity fuels clarity — and what it takes to keep showing up when business gets hard — this episode is your reminder that integrity and adaptability win the long game.

Most entrepreneurs can rattle off their revenue goals or marketing plan without hesitation. But ask them what they stand for — what they refuse to compromise on — and the silence is deafening. In this solo episode of Small Business Big Deal, Tracy pulls back the curtain on the one thing that makes or breaks your business: your values. Far from being fluffy buzzwords, your values shape who you hire, how you market, what clients you accept, and how you lead your team. You'll hear real stories from Tracy's own journey (including how ignoring her value of simplicity nearly derailed her business and family) and from clients who discovered that being out of alignment with their values was the source of their frustration, burnout, and resentment. By the end of this episode, you'll walk away with: A step-by-step process to uncover your top five values. Reflection questions that reveal what truly drives you. A framework for aligning your business decisions with your values. Practical ways to use values as a compass for growth, boundaries, and joy in your work. Your business doesn't have to drain you — it can (and should) reflect who you are at your core. This episode will help you make sure it does. ✨ Free Resource: Take the Values Assessment to uncover your top five values and put this exercise into action right away

In this episode of the Small Business Big Deal podcast, host Tracy Jepson interviews Roxanne Alford, the founder of Short Stuff, a sustainable children's clothing brand inspired by her experiences as a new mom. Roxanne shares her journey from working in IT sales to launching her own brand, driven by a desire for gender-neutral clothing and educational products for children. The conversation explores the challenges of entrepreneurship, including sourcing sustainable materials, balancing personal life with business, and the importance of community feedback. Roxanne emphasizes the significance of resilience, personal growth, and breaking stereotypes in the fashion industry. In this engaging conversation, Roxanne Alford shares her journey as an entrepreneur, discussing her unique skills, the launch of her new collection, and the importance of support systems for women in business. She emphasizes the significance of pursuing one's passions, balancing motherhood with entrepreneurship, and the value of community among women. Roxanne also reflects on her aspirations for her business and the legacy she hopes to create. Website: https://shortstuffshop.com/ Instagram: https://www.instagram.com/shortstuff.shop/ Code to Shop: SHORTSTUFF30 Chapters 00:00 Introduction to Roxanne Alford and Short Stuff 03:33 The Journey to Entrepreneurship 05:54 Sourcing Suppliers and Sustainability 08:07 Balancing Personal Life and Business 10:33 Financing the Startup 11:39 Risks in Entrepreneurship 14:22 Personal and Professional Growth 16:43 Inspirations and Resilience 18:34 Learning from Experience 20:18 Creating a Sense of Home 21:54 Feedback and Community Engagement 23:27 Gender Neutrality in Children's Clothing 25:08 Fun and Useless Skills 25:54 Useless Skills and Hidden Talents 27:21 The World of Wonder Collection 30:08 Lunch with Influential Figures 32:08 Building a Legacy through Business 35:43 Encouragement for Aspiring Entrepreneurs 39:07 Balancing Motherhood and Entrepreneurship 42:13 Where to Find Short Stuff Shop

In this conversation, Tracy Jepson interviews Sabrina, the founder of Golf Angels, a brand aimed at making golf more accessible and relatable for women. They discuss the inspiration behind the brand, the challenges of starting a business, the importance of self-care, and how Golf Angels aims to break traditional norms in the golf industry. Sabrina shares her journey as an entrepreneur, the support she receives from her community, and her vision for creating a brand that resonates with women golfers. In this conversation, Sabrina and Tracy discuss the evolution of women's golf apparel, the importance of celebrating small wins in entrepreneurship, and the challenges of building a niche brand in a traditionally male-dominated industry. They emphasize the need for modern branding that resonates with younger generations and the significance of community engagement in growing a business. 00:00The Birth of Golf Angels 05:22Overcoming Startup Challenges 11:26A Day in the Life of an Entrepreneur 19:22Breaking Traditions in Golf 25:57Celebrating Small Wins in Entrepreneurship 31:43Advice for Aspiring Entrepreneurs in Niche Markets Connect! Website: golfangelshop.com IG : @golf_angel_shop

Jess Freeman, the owner of Jess Creatives, specializes in high impact websites and SEO for business owners. She helps them improve their branding, websites, and SEO to generate more leads and traffic. Jess explains that she was drawn to SEO because she saw many business owners struggling with social media and not getting results from their websites. She combines her creative and analytical skills to help clients improve their online presence. Jess also shares her journey as a business owner, including the importance of setting boundaries and finding a balance between client work and working on her business. In this conversation, Jess and Tracy discuss the importance of Pinterest and SEO in business marketing strategies. They highlight the benefits of using Pinterest as a search engine and the potential for businesses to reach their target audience through the platform. They also discuss the significance of staying updated on SEO trends and offer tips on how to do so. The conversation concludes with advice for entrepreneurs, emphasizing the importance of pivoting and staying consistent in business. KEYWORDS: websites, SEO, branding, social media, business owner, boundaries, client work, working on the business, Pinterest, SEO, business marketing, search engine, target audience, staying updated, pivoting, consistency 00:00 Introduction and Background 02:49 The Importance of Websites and SEO 08:51 Transitioning to Full-Time Business Owner 11:52 Setting Boundaries and Managing Clients 19:58 Balancing Client Work and Working on the Business 32:01 Effective Marketing Channels: Instagram, Threads, and YouTube 35:04 The Value of Pinterest for Business Owners 35:25 Harnessing the Power of Pinterest 38:02 Staying Updated on SEO Trends 43:36 The Importance of Pivoting in Business 45:28 The Power of Consistency 49:18 Understanding Your Clients and Their Platform Usage 52:06 Using Data and Analytics to Inform Content Creation 53:46 Investing in Education and Seeking Guidance 55:02 Building a Strong Online Presence 57:21 Adapting to Changes in Algorithms 58:36 The Benefits of Having a Website with Optimized SEO 01:00:36 Overcoming Challenges and Achieving Success

On today's podcast, we're talking with Dennis Crosby, owner of Crochet Media Group, an online subscription that focuses on the arts and crafts niche, especially crocheting. Find out how his business is thriving, even during COVID. Read more: https://tracyjepsonpodcast.com/media/ep-38-online-magazine-business-booming-even-during-covid/1484/ About our guest: https://denniscrosby.com/ What we discuss on this episode: 1:32 – Meet Dennis 12:55 – How he ended up working on a magazine 19:53 – Why he continued magazine 24:45 – Building teams 29:06 – Hiring 34:16 – Personal development 40:59 – What's next

On today's podcast, we're talking with Todd Bertsch, owner of Evolve Marketing and a leader in the web design industry. Find out how this self-described "true-born leader" created his company. Read more: https://tracyjepsonpodcast.com/podcast/ep-36-how-a-true-born-leader-created-his-own-marketing-team/1468/ About our guest: Todd is an award-winning web designer, author, educator, and lecturer, and speaks regularly throughout the region on various web-related topics. He holds a BFA from The University of Akron in graphic design. His web experience and marketing strategies are what separate him and Evolve from others in the web industry. Helpful Resources: https://www.evolvemarketingteam.com/ https://www.linkedin.com/in/toddmbertsch/ What we discuss on this episode: 1:29 – Meet Todd 3:29 – Why entrepreneurship 7:34 – Work-life balance 17:54 – Delegation 20:29 – First hire 25:38 – Accounting 29:08 – What he wishes he knew 33:01 – Failure 33:36 – How his business is different 39:33 – Advice for new business owners 42:05 – Contact Todd

On today's podcast, we're talking with John Briggs, founder and CEO of Incite Tax. John graduated from Brigham Young University with a Master of Accountancy in Tax. He worked on corporate taxes and trusts in Orange County, Calif., with Deloitte & Touche, one of the four largest national accounting firms. Read more and get additional resources here: https://tracyjepsonpodcast.com/podcast/ep-34-accounting-firm-owner-helps-businesses-navigate-tricky-tax-system/1456/ About our guest: https://incitetax.com/about-the-team/ What we discuss on this episode: 1:09 – Businesses 4:15 – Anti-tax 6:40 – Scary IRS letters 11:40 – Entrepreneurship 16:47 – Work-life balance 23:07 – Personal development 28:20 – Making an impact 33:32 – Company culture 38:42 – Employees 39:37 – Dream gifts 40:26 – New entrepreneurs 44:26 – Contact John

On today's podcast, we're talking with Lauren Goldstein, founder and CEO of the boutique business strategy consulting firm Golden Key Partnership. Read more and get additional resources here: https://tracyjepsonpodcast.com/podcast/ep-32-the-business-doctor-helps-clients-get-unstuck/1440/ About our guest: https://www.goldenkeypartnership.com/ What we discuss on this episode: 1:34 – Meet Lauren 2:29 – How she started 6:15 – How she helps clients 8:27 – Her team 11:30 – Hiring people 14:06 – Tools she uses 18:44 – Work-life balance 24:35 – Hustle culture 25:45 – Continued education 27:41 – Misconceptions 31:32 – Types of clients 34:07 – Contact Lauren

On today's podcast, meet Mike Michalowichz, creator and author of Profit First, which hundreds of thousands of companies across the globe use to drive profit. Find out how he made a fortune, lost it all and is now helping others. Read more and get additional resources here: https://tracyjepsonpodcast.com/entrepreneur/ep-30-business-owner-and-author-shares-his-profit-first-approach/1426/ About our guest: https://mikemichalowicz.com/ Connect with Mike: https://mikemichalowicz.lpages.co/small-business-big-deal-podcast-page/ What we discuss on this episode: 1:34 – Meet Mike 3:35 – Crash and burn 6:11 – His first book 8:50 – Being profitable is OK 11:59 – Key foundations to business 13:54 – Finding your niche 17:23 – Work-life balance 19:34 – Educating himself 21:29 – Worthwhile investments 23:32 – Best investment in his business 24:39 – Contact Mike

On today's podcast, meet Kim Kiel, a sales and direct response strategist and founder of the boutique copywriting agency, Kim Kiel Copy. Find out how she created her business around her family's needs. Read more: https://tracyjepsonpodcast.com/freelance/ep-28-how-kim-kiel-designed-a-copywriting-business-around-her-life/1415/ About our guest: https://www.kimkiel.com/ Get the Ultimate Checklist for Magnetic Copy that Attracts & Sells: https://www.kimkiel.com/magnetic-copy-checklist What we discuss on this episode: 1:19 – Starting her business 2:13 – Nonprofit industry 6:48 – Quitting her job 8:37 – Entrepreneurs in her life 10:18 – Work-life balance 12:34 – Clients 15:27 – Online influencers 18:53 – Best investments 23:27 – Home life 27:58 – Focus 29:59 – Inspiring clients 34:35 – Giving back 37:25 – Contact Kim

On today's podcast, meet Alexa Hallberg, a serial entrepreneur, philanthropist and business badass. Find out why she has made it her mission to help other women in business. See the show notes: https://tracyjepsonpodcast.com/entrepreneur/ep-26-serial-entrepreneur-wants-to-help-other-women-business-owners/1398/ Connect with Alexa: https://alexahallberg.com/ https://lexandcompany.co/ What we discuss on this episode: 2:09 – How Alexa created her photography business 5:37 – College 7:03 - Skills 10:06 – Adding a studio 13:36 – Big, exciting things happening 28:51 – Opening her store 32:32 – Marketing 34:09 – Mentors 35:30 – Education 43:50 – Advice for new entrepreneurs 47:02 – How to contact Alexa

On today's episode of the Small Business, Big Deal podcast, our guest is Aimee Rosenow, owner of Evoke Creative Topeka. Find out why she left one business and started another and how her work-life balance has changed. Read more: https://tracyjepsonpodcast.com/media/ep-24-boutique-business-owner-focuses-on-work-life-balance-and-helping-women/1383/ About our guest: Aimee is a family-oriented, small business consultant focused on helping retail shops and boutiques clearly demonstrate their brand through website design, email marketing, and social media. As a former boutique owner and mom of three, Aimee comes to her clients from a place of empathy and understanding. Her experience gives her a unique perspective and drives her mission of giving boutique owners back the time to do the things they truly love. What we discuss on this episode: 1:02 – Meet Aimee 2:30 – Friendship and business 3:27 – Children's boutique 5:29 – Work-life balance 8:45 – Getting back into business 10:22 – Boundaries 15:55 – Advice 20:29 – Turning down clients 23:14 – Networking 28:18 – How to contact Aimee 30:06 – Bonus content