Terry Pappy
My Solopreneur Life
It’s for sure that running a one-person business takes courage, execution, and a whole lot of learning—but you don’t have to figure it all out by yourself. My Solopreneur Life is your go-to resource for confidence-building inspiration, actionable business insights, and real talk about what it takes to be a successful solopreneur, hosted by 20-year solopreneur, Terry Pappy. In addition to tips on solopreneur marketing, sales, branding, and customer experience, you’ll also hear from fellow solopreneurs who generously share their wisdom, wins, and lessons learned along the way. In a world where a...
Where to listen?
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Episodes
MSL 306 - Confident selling for introverts: three ways to turn awkward calls into authentic wins 20.10.2025
In this episode of My Solopreneur Life , I'm walking you through three strategies that helped me go from dreading sales calls to confidently closing deals, and how you can do the same, even if you're naturally introverted. You'll discover how to reframe those uncomfortable cold calls into friendly conversations where you're genuinely helping people solve problems. I'll show you three specific scen...
MSL 305 - Stop overthinking sales: practical steps to prospect, decide, and move forward with Eric Shulman 13.10.2025
In this second part of my conversation with sales trainer Eric Shulman, we get tactical. Eric lays out clear steps for solopreneurs who want to stop circling in indecision and actually build momentum in their sales. From reframing networking and prospecting to tackling “head trash” and learning to make quick decisions, this episode is packed with real strategies you can use right away.
MSL 304 - Why sales doesn’t have to feel salesy: building radical empathy with Eric Shulman 06.10.2025
In this episode of My Solopreneur Life , I sit down with sales trainer Eric Shulman to break down why selling isn’t about pressure or pushing—it’s about connection. Eric shares how to replace fear with curiosity, why “radical empathy” changes everything, and how to build instant trust without coming off like every other salesperson.
MSL 303 - Unlock sales confidence: Six proven tips with a few AI prompts to turn rejection into revenue 29.09.2025
In this episode, I dive deep into one of the toughest challenges every solopreneur faces: overcoming the fear of rejection when approaching sales conversations. I unpack the six mindset shifts and tactical steps that have truly helped me transform every "no" into valuable feedback and greater confidence. From normalizing anxiety and learning to detach personal meaning from rejection, to reframing...
MSL 302 - How your financial mindset sabotages (or supercharges) your solopreneur sales so you can grow revenue faster 22.09.2025
In this episode, I get real about why my financial mindset used to sabotage my sales and how I changed it. I share personal stories of fear and financial stress, how those anxieties bled into client conversations, and the turning point that let me sell with calm clarity. You'll hear actionable strategies for separating your financial reality from your selling energy, helping you show up confidentl...
MSL 301 - Why selling feels so hard when you ARE the business (and the three hidden challenges no one talks about) 15.09.2025
Here’s the thing: nobody warns you how weird, and sometimes downright cringey, it feels when you try to sell your own services for the first time. If you’ve ever wondered why asking for business is so much harder when you’re the product, you’re not alone. In this episode, I open up about my own early sales stumbles, breakout moments, and the wild learning curve faced by solopreneurs who never plan...
MSL 219 - Season 2 Finale: What Starting Really Takes Plus a Sneak Peek at Season 3 08.09.2025
In this Season 2 finale of My Solopreneur Life , I recap what “starting” really took for me and the breakthroughs I had along the way. I share why starting is not a one-time event but a choice I make at key moments, guided by intention, mindset, and the story I tell myself. I talk about how inquiry and qualitative research shaped my practice and how spotting client patterns led me to my Better Thr...
MSL 218 - Membership Models, Pivots and Passion: A Solopreneur’s Playbook with Natalie Benamou 01.09.2025
In this episode of My Solopreneur Life , host Terry Pappy talks with Natalie Benamou, founder of Her C-Suite, about launching and growing a purpose-driven business in the second half of life. Natalie shares her journey from corporate trade show executive to community builder for high-achieving women, including how COVID-19 forced a pivot, the challenges and lessons of running a membership model, a...
MSL 217 - Surviving the Solopreneur Rollercoaster: Real Advice with Pia Silva (Part 2) 25.08.2025
In the second part of my interview with Pia Silva, author of “Badass Your Brand,” we explore how solopreneurs can build businesses that truly last—even when things plateau or feel like a rollercoaster. Pia gives practical advice for sustaining growth, tackling dry spells and peaks, and freeing yourself from the need for “perfect” monthly income. We talk honesty in client relationships, gaining con...
MSL 216 - How to Set Prices and Build a Profitable Solo Business with Pia Silva (Part 1) 18.08.2025
In this first part of my two-part conversation with Pia Silva, author of “Badass Your Brand,” we dive into the practical foundations of building a sustainable solopreneur or small agency business. Pia shares how her simple, bold business model transformed my own career, and we discuss real-world strategies for pricing your services, building confidence, and creating a business that lasts. Pia expl...
MSL 215 - From Corporate to Solopreneur: Building a Business on Authentic Relationships with Stevie Johns 11.08.2025
In this episode, I catch up with Stevie Johns, founder of Inkwell Management. Stevie shares her personal story of leaving a corporate career to start her own boutique speaker management agency, and how she grew her roster from three to eighteen speakers in her very first year. We talk about the importance of building authentic, heart-driven relationships and how that’s been the foundation of her b...
MSL 214 - From Radio to Content Marketing: Lessons for First-Time Solopreneurs with Penney Fox 04.08.2025
In this episode, I sit down with Penney Fox, content marketing strategist and 26-year solopreneur veteran. Penney shares her journey from building websites after a long career in radio, to becoming an authority on content and marketing. We talk about the realities of starting your own business, dealing with self-doubt, and evolving your offerings over time.
MSL 213 - Tips from Dale L. Roberts to Stay Motivated and Avoid Burnout as a Solopreneur (part two) 28.07.2025
In part two of my conversation with Dale L. Roberts, Dale shares real-world advice and actionable steps for solopreneurs at every stage. We dig into practical considerations when starting a solo business—like making sure you have a financial safety net, getting educated about your field before “burning the boats,” and the powerful impact of finding a mentor. For those who’ve already taken the leap...
MSL 212 - Solopreneur Mindset: Dale L. Roberts on Early Struggles, Coaching, and Book Publishing Success (part one) 21.07.2025
In this first part of my two-part conversation with Dale L. Roberts, I talk with Dale about how he got started as a solopreneur and self-published author. Dale shares how a challenge from his corporate wellness coach led him to write his first fitness book—something he’d always dreamed of but never pursued seriously until that moment. Dale talks honestly about those early days: the influence of hi...
MSL 211 - 7 Things to Go From "What Now?" to Starting Your Solopreneur Business 14.07.2025
In preparation for a talk to a group of folks considering starting their own business, I worked up a list of 7 items that matter A LOT. Here they are: 1. Finances - get on top of your finances before doing anything else 2. Passion - be clear on what you want to do 3. Mindset - secure a growth mindset 4. Relationships - your network is your gateway to success 5. Invest - get a coach to guide you al...
MSL 210 - How to Turn a Passion Project Into a Solo Business: The RxRoundtable Story (part two) 07.07.2025
Meet Harry Travis, solopreneur and ex-specialty pharmacy executive turned community building and network genius. Harry is a client of mine who I met in late 2024. He has a wonderful two part story (part one is episode 209, part two is episode 210) of his journey into solopreneurism and shares detailed challenges and realizations he faced when he launched his new consultancy and membership business...
MSL 209 - From Corporate to Consulting: First Steps for Solopreneurs with Harry Travis (part one) 30.06.2025
In this episode, I sit down with my client—and now friend—Harry Travis, who shares his inspiring journey from a long corporate career in pharmacy and healthcare to building his own solopreneur business. Harry talks about making the leap after leaving CVS Caremark, reinvesting in himself through executive education, and how classic networking led to the creation of the RX Roundtable—an ever-growing...
MSL 208 - Starting Your Business Opportunities Through Relationships 23.06.2025
Before anything else, when starting a business or leveling up a business, solopreneurs must have a strong network. Building relationships as an ongoing effort will lead to more opportunities for people to help you, you to be of service to others, and for people to know about you and the problems you solve. Most importantly, they should know the kind of person you are. That you have integrity in yo...
MSL 207 - Starting to Leverage the Story Process to Grow Your Business 16.06.2025
Your story will make or break your solopreneur business success, depending on how you use it. If you are intentional about creating a new story about your business, how you sell, how you serve clients, how you deliver value, how you market and promote your business, you'll find each area rewards you with positive results. If your story is defeatist, negative, or self-demeaning, like you're not goo...
MSL 206 - Starting in the Face of Strong Resistance 09.06.2025
Here’s an easy three-step process to blast through any resistance keeping you from starting a new business, project, or any endeavor you want to accomplish.
MSL 205 - Starting a Solopreneur Business and Facing Fears and Negative Beliefs 02.06.2025
Starting a new business is exciting and intimidating, especially if you've left the corporate world or a longstanding job and are at a loss on where or how to start. But before you figure out the practical stuff, you need to get your mindset up to speed with where you want to go. In this episode, I talk about the fears and diminishing beliefs that can thwart your progress from the get-go and how t...
MSL 204 - Starting to Use Visualization with AI to Grow Your Solopreneur Business 26.05.2025
Learn how to incorporate AI to help you visualize positive outcomes for your business. Your success begins with your imagination, and when you focus on what you want, lean into positive outcomes, before you know it, magical things happen. And, you can use AI to help craft some very creative scenarios that you can deliberately think about and visualize to stay positive and open to inspired action t...
MSL 203 - Starting to Use AI to Supercharge Your Solopreneur Inbound Marketing 19.05.2025
Let’s talk about how to use the right AI prompting to get specific marketing content. A process I use is to reverse engineer an end result—closing a new client—so you can develop the right kind of content for your inbound marketing campaigns.
MSL 202 - Designing Your Consulting Business at the Start 15.05.2025
This episode is about starting a consulting or service-based business—especially if you’re riffed from a long-term corporate role—and how to not miss the most important part of designing your business versus just doing the same old same old but on your own.
MSL 201 - Introduction to Season 2 on Starting - A Family of Starters 05.05.2025
Kicking off season two in this episode which is dedicated to starting. I share more about my family members and how their entrepreneurial DNA got them to start their businesses and projects. Starting is a little appreciated segment of the creative process where we conjure something magical that will be the bridge to us making money, helping others, and doing work we love. But it all has to begin w...
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