Josh Wollaston is co-founder of SPG Capital, focused on private lending and rental properties. He reveals how W-2 income helped fund the first rental, how a BRRRR-style strategy changed the capital equation, what happened when rising interest rates dried up deal flow after he left Citibank, and why the real entrepreneurial shift starts when we move from owning assets to solving market problems.

Josh Wollaston is co-founder of SPG Capital, a private lending company operating alongside a multifamily rental portfolio. Beginning with a single rental property purchased in 2016 while working a W-2 role at Citibank, he spent seven years scaling to a 50-plus unit portfolio using a BRRRR-style approach that recycled private capital through distressed assets. After leaving corporate life in 2022, he pivoted into private lending when rising interest rates collapsed the deal pipeline and now focuses on connecting the firm's investor base with other local operators. Josh approaches entrepreneurship as an internal shift from employee to builder, solving market problems creatively and scaling through partnership and investor relationships.

Josh explains:

◼ Why did seven years of a W-2 grind become the only path to going full-time?

◼ How did a college soccer teammate end up doing 70% of the work?

◼ What made a boss promise a $50,000 raise if things fell apart?

◼ Why did the deal pipeline collapse from eight projects to one in three months?

◼ How did a shrinking market accidentally birth a private lending company?

◼ What separates a real estate investor from an actual entrepreneur?

◼ Why does Josh stop working at 3:30 every single day?

◼ How do twins on the way change the math on quitting?

A forced pause created the space for entrepreneurial creativity, and AI became the tool that turned that creative space into immediate, measurable client value. In this episode, we talk about how hives in paradise stopped everything in its tracks, what happened when things finally slowed down, and how building a website in just four hours completely reframed the way clients work alongside AI.

Together, we explore AI-enabled entrepreneurship, the role of critical thinking in an AI-first world, and why every initiative should tie back to ROI from day one.

We dive into how a demanding quarterly season led to a forced reset that ultimately reshaped their approach to business, client work, and innovation — using AI not as a replacement for human thinking, but as a tool to amplify it.

Whitney Owens shares how an employer shutting down overnight forced her into practice ownership and ultimately shaped her approach to scaling a 17-plus-therapist group practice in Savannah, Georgia. We explore her shift from identity-based to values-based hiring, the role of SOPs in reclaiming sanity from recurring high-stakes work, and why the founder's ability to stay present and metabolize disappointment is often the real constraint on sustainable growth.

Lindsay Goldfarb didn't set out to build a therapy business, she started seeing a few clients to bridge a gap between jobs and accidentally discovered a niche serving young adults who wanted a therapist they could actually relate to.

Lindsay walks us through the full arc of going from solo clinician to founder of a growing group practice in Washington, D.C. She shares how overwhelming demand, a data-minded approach to risk, and a willingness to invest early — in admin support, branding, and physical space — allowed her to scale without burning out or losing the culture she was building.

For practice owners and service-based founders navigating the messy middle between doing the work and running the business, this conversation cuts to the heart of what it actually takes to make that shift — and why waiting until you're "ready" often means waiting too long.

Lindsay brings a rare combination of clinical training and analytical thinking to the business side, having grown the Sterling Group from a solo practice to a multi-therapist team while navigating two maternity leaves and a post-2020 return to in-person care.

Key takeaways include why hiring admin support before your first clinician creates leverage, how brand and vibe function as trust infrastructure rather than just marketing, the importance of slowing down to build systems after a fast growth phase, and why in-person connection is making a strong comeback with younger clients and teams alike.

Topics covered: solo-to-group practice transition, niche discovery, early-stage hiring strategy, brand investment for professional services, founder-to-CEO mindset shift, culture and accountability tension, demand-driven growth, in-person vs. virtual service delivery, accessibility in mental health.

Resources: The Sterling Group, Psychology Today provider profiles, Dan Martell's delegation framework, Michael Gerber's concept of the entrepreneurial seizure.

If you're a practice owner or service-based founder building something bigger than yourself, subscribe so you don't miss the conversations that make the journey feel a little less lonely.

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Episode Produced by Riggg Productions

Most business owners know they need to stop doing the work and start leading it — but the real bottleneck is the layer between vision and execution: managers who were never taught how to think like owners, develop people, or connect daily tasks to business outcomes.

In this episode, Wendy Sauré shares her career arc from running Jenny Craig centers to coaching small business owners through Michael Gerber's E-Myth organization to helping scale Siegfried from a small firm into a national enterprise. Along the way, she unpacks why the individual contributor-to-manager transition is the most underleveraged growth lever in mid-size businesses — and why efficiency without effectiveness quietly erodes culture, talent pipelines, and execution.

With organizations getting leaner, wages rising, and AI reshaping workflows, the pressure on managers has never been higher — yet most are still figuring it out alone, without frameworks, financial literacy, or real development from above.

Wendy brings nearly three decades of experience developing leaders inside entrepreneurial and private companies, from franchises to hundred-million-dollar professional services firms, giving her a rare vantage point on what actually makes managers effective at every stage of growth.

Expect practical insights on delegation as multiplication, why rigorous feedback is an act of care, how financial literacy unlocks better decision-making at every level, and why the "work on it, not in it" principle applies as much to managers as it does to founders.

Topics: IC-to-manager transition, E-Myth frameworks, delegation and talent development, financial literacy for managers, AI as a human-centered efficiency tool, scaling through people and systems, the cost of efficiency without effectiveness.

Resources: E-Myth Revisited by Michael Gerber, Scaling Up by Verne Harnish, Traction by Gina Wickman.

Subscribe to C-Suite Chronicles wherever you listen to podcasts and share this episode with a manager in your organization who deserves better support.

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Produced by Riggg Productions

Most founders walk around convinced everyone else has it figured out — this episode proves otherwise and shows why naming that feeling is the first step toward better leadership.

In the debut episode of C-Suite Chronicles, co-hosts Jeremy and Wendy share how they reconnected after nearly a decade apart and why they decided to build a podcast rooted in honest conversation about what it actually takes to run a business. Jeremy walks through his origin story — growing up in a family automotive shop, facing crippling anxiety as a door-to-door salesperson, navigating depression and loss in his early twenties, and eventually finding his footing as a fractional COO and integrator. Along the way, they explore how imposter syndrome shows up at every stage, why entrepreneurship is fundamentally a relationship game, and how community and vulnerability can replace isolation and fear.

With AI reshaping how businesses operate and founders feeling more pressure than ever to have all the answers, this conversation is a grounding reminder that the human side of leadership — connection, honesty, and showing up even when it's uncomfortable — still drives the outcomes that matter most.

Jeremy brings years of hands-on experience as a fractional COO working with small and mid-size businesses, while Wendy draws on decades of leading peer-to-peer seminars and coaching business owners through growth and transition. Together, they bring complementary perspectives shaped by real operating experience, not theory.

Listeners will hear why tracking relationships like a KPI can transform your business development, how failure and anxiety became catalysts for career clarity, what it looks like to use AI in a human-centered way, and why the most powerful thing a founder can do is admit they don't have it all figured out.

Topics: founder isolation, imposter syndrome, origin stories, fractional COO path, relationship tracking and behavior metrics, sales anxiety, family business dynamics, community building, human-centered AI adoption, SOP creation with AI, lead generation and conversion, entrepreneurial identity.

Resources: EOS (Entrepreneurial Operating System), Catalyst (fractional integrator network), Keith Ferrazzi's relationship management system, Chamber of Connection by Aaron Hurst, Wayne Dyer.

Subscribe and follow along as we bring more founders to the mic to share their real stories — because the best way to feel less alone in business is to hear someone else say what you've been thinking.

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Produced by Riggg Productions