Matt Symes is a transformation strategist who's worked with 500+ organizations and contributed to over $1 billion in profitable growth. In this episode, he breaks down the predictable revenue milestones where founder-led businesses hit a wall, and how to scale without losing your mind (or your life). If you're a founder making between $500K-$5M in revenue, this conversation is for you. We dig into sales systemization, why not all revenue is good revenue, and the concept of the "badlands"— that uncomfortable zone where you need a $5M company's infrastructure but can't afford it yet.

Matt's Origin Story (1:46)

His unique background: great-grandson of a subsistence farmer, grandson of a first-gen entrepreneur roofer, son of the first college-grad in his family who brought modern management systems from Procter & Gamble to a billion-dollar company in Canada. This mix of blue-collar work ethic and white-collar systems thinking shaped everything he does.

The Predictable Revenue Ceiling (5:44)

Why founders hit a wall at specific revenue points:

• $300-500K: You're selling yourself. It's "the Jessica Rhodes show"—your ability to close deals.
• $1M+: You're in the top 6% of businesses. Now you need systems beyond yourself.
• $5M+: Only 4% of the million-dollar businesses ever get here (2.4 out of 1,000 total). The whole game shifts from doing the work to managing processes.

The Shift from Doing to Managing (5:44)

Around $1.8M, you can't hold it together with duct tape and a couple of good people anymore. You have to go from:

• Managing the sale → managing the sales process
• Managing the job → managing the scheduling process
• Managing 2-3 people → managing HR and the entire employee lifecycle

Systemizing Your Sales Process (9:16)

The sales funnel has five predictable steps: Suspect → Prospect → Qualified Opportunity → Proposal → Yes/No/Nurture.

When you systematize it, you're not looking for a salesperson who's as good as you (they won't be). You're looking for someone who can hit 80% of your performance. Then you manage through five key metrics:

1. Total potential opportunities
2. Total dollar value of those opportunities
3. Cycle time (first contact to conversion)
4. Touch time (number of meetings required)
5. Conversion percentage

You meet with your sales leader for an hour a week to look at the health of the funnel and identify bottlenecks—not to do the sales yourself.

Not All Revenue is Good Revenue (13:20)

This was a huge theme in Jess's journey too. Having clients that don't fit your model costs you way more time and energy than their revenue is worth. Matt breaks it down:

• You need to know: What problem do I solve? For who? What's the value?
• You are ONE part of a three-part equation (you + customer + value created).
• The same expertise deployed with different clients yields completely different results. Example: Matt can do 2 days of strategy work for a cohort of 10 companies at $3,750/month each = $37,500 total. Or $20,000 for one company. Or a nonprofit at $2,000. The same work, vastly different margins.
• Know your ticket price and work backward. If Jess books Matt on a podcast and it brings 2 customers in 12 months, the investment pays for itself.

The Badlands: $1.8M-$5M Revenue (24:38)

This concept comes from Greg Crabtree's Simple Numbers. Between $1.8M and $5M, you need the full infrastructure of a $5-6M company (sales team, marketing team, HR systems, operations), but you can't afford any of it.

At around $2.2-2.3M, this hits hard. You're going to stretch something: your time, your bank account, or take outside investment. There is no calm way through the badlands.

Matt's grandfather (the roofer) ran into this. He hired family, got trucks running everywhere, but nobody was looking at the bottom line. Revenue is vanity, cash is sanity. So at a certain point, his grandfather said "enough." He gave everyone their trucks and ladders, scaled way back, got hyper-profitable, built a war chest, and retired at 49—fully funding his kids' education and leaving the family set up for life.

Build Your Business Around Your Best Life (23:32)

Don't ask: "How big can this business be?" Ask: "What do I want my life to look like? And how do I build a business that serves that?"

For Jess right now: she has two kids (10 and 13), she's driving to cheer practice four days a week, and she wants a lifestyle business that supports her being a present mom. That's not a failure. That's clarity.

For someone else, it might be: I want $500K in profit, I want to own 100% of the business (not be CEO), and I want to landscape two days a week because it fills my bucket.

Once you know your best life, you can say: What do I love doing in this business? What do I hate doing? Let's systematize the stuff you hate and find people who love it.

Using AI to Build Your Sales SOP (32:21)

Matt uses an AI note-taker in all his meetings. Take every sales conversation you've had (the wins and the losses), and use AI to extract:

• The objections that come up
• How you overcome them
• The flow of your pitch
• The close

Build the whole playbook in half a day of your time. Then hand it to someone and coach them through it. They won't convert at your rate at first, and that will annoy you. But you have to get past it.

Strategy is a Living Process (17:58)

Strategy isn't something you do once a year. The world, your market, your capabilities, and AI are all changing constantly.

Best practice: 90-day strategic reviews (not annual plans—people can't conceptually commit that far out).

Decision-making rhythm: Meet quarterly to look at where you're heading, what the world is doing, and what you need to do in the next 90 days. Then break it into a 4-week detailed work plan. This gives you peace of mind to ignore the noise and execute.

Levership Program (21:03)

Levership is a cohort-based, AI-first strategy program. It takes corporate strategy and makes it accessible to growth-minded founders without the $300K price tag.

$3,750/month includes:

• The strategic process (who do I want to be, what am I, where am I headed?)
• Building a financial pro forma (revenue + customer mix + product/service mix + capabilities + people needed)
• Quarterly strategic reviews
• AI integration (how to responsibly use AI in your business)
• Cohort support

Who they work with:

• Growth-minded entrepreneurs
• Looking to systematize so it doesn't require all your hours
• Ready to clarify (or have the conversation about) what you want long-term

What they do upfront:

• Free discovery call to see if it's a fit
• Build that financial model to make sure the money is actually there
• No charge until you both agree it's the right partnership for 12 months

Levership:

Website: https://levership.com/

What to expect: Book a free call with Matt or his co-founder Chris. They'll walk through whether this is the right fit for you.

Book Mentioned:

Simple Numbers by Greg Crabtree

This episode is a goldmine for women entrepreneurs, coaches, speakers, and moms building businesses while designing lives they actually want to live.

Jessica sits down with keynote speaker, executive coach, bestselling author, and podcast host Erica Anderson Rooney to talk about leaving corporate America, building a business from the ground up, and creating success without sacrificing time with family.

Erica shares the pivotal moment that made her realize she needed to leave her executive role, how she found her first clients through Facebook groups, and why she still intentionally says yes to strategic unpaid opportunities today.

Together, Jessica and Erica dive into networking, podcasting, motherhood, and the mindset shifts required to build a sustainable business that supports the life you want.

• How Erica transitioned from Chief People Officer to entrepreneur
• The surprising way she landed her first coaching clients
• Why doing free work strategically can accelerate business growth
• How to evaluate networking opportunities that actually produce ROI
• The importance of talking about your business in everyday life
• How podcast guesting and podcast hosting can become a powerful growth engine
• Ways to intentionally design your business around your family priorities
• Why building your business slowly and intentionally can be your greatest advantage
• How entrepreneurs can leverage existing communities (like sports parents and school communities) for business growth
• Creative ways to repurpose podcast content into books, communities, and long-term assets

"If you can't talk about your business, you can't have a business."

"The universe doesn't give you everything you want if you don't have the space for it in your life."

"I am building intentionally, and I am building slowly, and that is okay."

Connect with Erica:

• Website: https://www.ericaandersonrooney.com/
• LinkedIn: https://www.linkedin.com/in/ericarooney/
• Podcast: https://www.ericaandersonrooney.com/podcast
• Book: The AI Gap: Women, AI, and The Next Great Leap Forward: https://www.ericaandersonrooney.com/glassceilings

Erica Anderson Rooney is a keynote speaker, executive coach, corporate trainer, bestselling author, and founder of Her Collective. After rising quickly through the ranks of corporate America to become a Chief People Officer in her early 30s, she decided to leave the traditional corporate path to build a business aligned with her values and priorities. Today, she helps women break through barriers, build confidence, and step into positions of leadership and influence while creating lives they truly love.

This episode went places I did not expect, and I mean that in the best way.

Amber Caudle is a chef, author, speaker, and coach who has spent more than 20 years in the culinary world, including founding the Source Cafe. After battling disordered eating for 30 years, she discovered that healing her relationship with food was about so much more than what was on her plate. Through her coaching practice, Nourish Your Power, she blends nutrition, mindset, and somatic work to help women break free from harmful food patterns and reconnect with themselves.

Oh, and her book, Hungry: Reclaiming Food Freedom and Finding Peace in Your Body, dropped the day we recorded this. Talk about perfect timing.

In this conversation, Amber completely reframes what it means to eat well. We dig into why your nervous system state matters more than your macros, what actually happens to your digestion when you eat under stress, and why so many high-achieving women are walking around thinking they eat healthy while their bodies tell a completely different story. We also get into the difference between intuitive eating and mindful eating, why pleasure is actually a metabolic tool, and how your relationship with food mirrors your relationship with receiving in every other area of your life, including money, clients, and love.

This one is for every entrepreneur who eats lunch standing at the kitchen counter while checking email. You know who you are.

Connect with Amber: nourishyourpowers.com

Book: Hungry: Reclaiming Food Freedom and Finding Peace in Your Body on Amazon and Audible

Ready to share your story and expertise on podcasts? Schedule a free discovery call at interviewconnections.com/call.

If AI feels overwhelming, or you have been quietly avoiding it because you are not sure where to start, this episode is going to be a relief.

Len Ward is the founder and CEO of Commexis, an AI consulting and product development firm that helps businesses eliminate bottlenecks and scale through automation. He started his career as a stockbroker at Morgan Stanley and went on to become VP of Institutional Equity Sales and Trading at Credit Suisse, where he developed a sharp ability to read where things are heading. And where things are heading, according to Len, is a complete shift in how business gets done.

In this conversation, Len and I dig into why so many business owners are resistant to AI and what is really behind that fear. He breaks down the difference between what the media says AI can do and what is actually happening on the front lines, and his answer might surprise you. We also talk about the shift from what Len calls search and retrieve to solve my problem, and why the companies that make that shift fastest are the ones that will win.

Len shares real examples of how AI is cutting marketing budgets, eliminating unqualified leads, and putting sales teams on the one-yard line before they even pick up the phone. We also get into what he believes is the next most valuable job title inside every company, and why the idea that AI is going to replace human judgment is still a long way off.

If you are a coach, consultant, or business owner who knows AI is important but has not quite figured out how it fits into what you do, this episode will help you get clear.

Connect with Len: commexis.com or find him on LinkedIn at linkedin.com/in/lenward

Ready to get your story in front of the right audiences? Schedule a free discovery call at interviewconnections.com/call.

When George Wiseman first reached out to Interview Connections, I had no idea that our conversation would move me to tears. George is an inventor, engineer, and founder of Eagle Research, and his story is one of the most powerful I have ever heard on this podcast.

George has spent decades developing Brown's gas technology, originally as an alternative energy solution for fuel efficiency and combustion systems. But it was a series of deeply personal experiences, including years as the full-time caretaker for his late wife as she battled lupus, that transformed his life's mission entirely.

In this episode, George shares how Brown's gas went from a fuel-saving technology to something he believes saved his own life after the devastating loss of his wife in 2016. He walks us through the science of hydrogen therapy, why most people are hydrogen deficient, and the remarkable changes he experienced in his own body after inhaling Brown's gas, from the disappearance of a 50-year-old virus to the healing of a heart murmur he had carried since childhood.

We also talk about why stories like George's rarely make it into traditional media, and why podcasting remains one of the most powerful platforms for ideas that challenge the status quo.

If you have been curious about hydrogen therapy, alternative wellness, or what it looks like to rebuild your life around a mission that is bigger than yourself, this episode is for you.

Connect with George and grab his free ebook on how Brown's gas can support life extension and whole-body health: https://eagle-research.com/can-hydrogen-help-you-live-longer-download/

Are you ready to share your story on podcasts? Schedule a free consult at interviewconnections.com/call

If you have been pouring your heart into writing a book and wondering how to actually get people to read it, this episode is for you.

I was introduced to Jenn T. Grace by one of our clients, Linda Hunt, and the moment we got on a call, I knew I needed to get her on the show. She is an award-winning author, nationally recognized speaker, and publishing strategist with more than 20 years of experience in marketing, communication, and storytelling. She is the founder of Publish Your Purpose, a certified B Corp hybrid publisher, and the creator of the Institute for Author Growth and Impact, an educational platform supporting nonfiction and memoir writers through every stage of their author journey.

And I have to be honest: after nearly 400 episodes of this podcast, I somehow never did an episode about using podcast appearances to promote a book. Jenn helped me fix that.

In this conversation, we get into why podcast guesting converts so much better than traditional media for authors, what realistic book sales numbers actually look like, and why the authors who talk about their book constantly are the ones who win long-term. Jenn also shares the sweet spot for when to start marketing your book, how to grow your email list before your book even launches, and how some of her clients have landed six-figure consulting deals simply by getting their book into the right hands.

If you are an entrepreneur, coach, or thought leader who is writing a book or thinking about writing one, this episode will show you exactly how to use podcast guesting to build momentum before, during, and long after your launch.

Connect with Jenn: publishyourpurpose.com

Ready to get booked on podcasts and promote your book? Schedule a free discovery call at interviewconnections.com/call.

John McNellis didn't set out to become one of the most respected commercial real estate developers on the West Coast. He was a journalism major turned lawyer who stumbled into real estate—and never looked back. In this episode, John shares the honest, unfiltered story of how he built a career deal by deal, including the wins, the spectacular losses, and everything in between.

John is the author of Making It in Real Estate, now in its third edition with 34 new chapters. What started as a 25,000-word insider favorite has grown into required reading at Stanford, Berkeley, Clemson, Vanderbilt, Georgetown, and universities across the country. Students and seasoned investors alike call it their real estate Bible.

In this episode, we cover:

• Why real estate is one of the only businesses you can start as a side gig—no matter what your day job is
• John's origin story: from a $25,000 duplex at age 24 to shopping center development across California
• The skills that matter most in real estate (hint: emotional intelligence and listening rank higher than you'd think)
• Why the path to success was anything but linear—and what John's worst deals taught him
• How to manage the psychological weight of big money and real risk
• The "four Ds" formula for finding your first investment property
• Why John recommends starting small, staying conservative, and building your reserves before swinging for the fences
• His take on flipping land vs. houses—and why he'd never put debt on bare land
• What actually drives him (spoiler: it was never about the money)

Resources mentioned:

Making It in Real Estate by John McNellis — available on Amazon, Audible, and as an e-book. Bulk orders of 25+ copies are available at $10/copy (vs. $20 retail) at https://www.johnmcnellis.com

Malcolm Reid Sr. is the founder of ProGlobal Business Advisors, a business-in-a-box model that has helped over 1,000 coaches worldwide build profitable, values-driven practices over the past 12 years. Malcolm provides coaches with everything they need to run a thriving business — positioning, systems, enrollment processes, delivery frameworks, software, and long-term operational support — all branded to the coach.

In this episode, Jess and Malcolm get into a conversation that's been brewing since Malcolm joined Interview Connections earlier this year. When Jess's salesperson left, it was Malcolm who had planted the seed that the best closers aren't salespeople — they're the coaches themselves. That insight changed the way Jess runs her business, and in this episode they unpack why.

What we cover:

• Why Malcolm's company doesn't have a sales team — and how the people doing the fulfillment are also the ones doing the enrollment
• The difference between a sales call and a selection process (and why it matters for client quality and retention)
• The "business in a box" model — what it means, how it works, and why it's modeled after a franchise but branded entirely to the coach
• How Malcolm helps coaches get clients through a diagnostic tool that finds six figures of hidden revenue in under 60 minutes — before asking for the business
• The power of strategic alliances and JV partnerships as a low/no-cost client generation strategy
• Malcolm's origin story: growing up in Baltimore, a conviction, and the turning point that led him to help small business owners build the lives they dreamed of
• Why both Jess and Malcolm believe that money is a result — not a motivation — and how leading with genuine care builds businesses that last

Connect with Malcolm:

Grab Malcolm's book, Massive Action, which outlines the 22 strategies he uses with his clients: 100KLeak.com

What if financial freedom has nothing to do with how much you accumulate? Dan Scott, founder of Spotlight Advisory Group, built his career around a simple but powerful reframe: financial freedom is about having enough money to live in full alignment with your purpose.

In this episode, Dan shares the philosophy behind his work with artists, entrepreneurs, and creatives, the origin story of his firm, and what his upcoming book, The Experience of Financial Freedom, is really about. He also opens up about his lifelong relationship with music, his punk rock roots, and why he sees folk music as the original punk.

What We Cover:

• Why "enough" is more important than "more" when it comes to money
• How Dan's quest for happiness at age 16 led to his definition of financial freedom
• The connection between purpose, positive psychology, and financial design
• Why money was never meant to be the goal, and what happens when we treat it like one
• His work with artists and creatives, and why he says everyone is creative
• His upcoming book The Experience of Financial Freedom and what's inside it
• The through-line between punk rock, folk music, and freedom as a philosophy
• Why he thinks the entertainment industry is a tool for artists, not the measure of success

About Dan Scott:

Dan Scott is the founder of Spotlight Advisory Group, a personal and business management firm working with artists, entrepreneurs, and creatives. Through financial strategy, accountability, and mindset work, he helps clients break free from industry constraints and build lives that reflect their values and long-term vision. He is also the soon-to-be author of The Experience of Financial Freedom.

Connect with Dan:

Website + weekly blog: www.spotlightadvisorygroup.com

Email: [email protected]

Want to land more podcast appearances and grow your thought leadership? Visit interviewconnections.com/call to schedule a call.

Suzanne Roberts, Principal of UnifyingSolutions, is a seasoned coach, author, facilitator, and speaker, with over five decades of experience in guiding organizations and individuals toward transformative change. Since 1979, she has worked with a diverse range of corporations, businesses, and non-profits, specializing in leadership development, cultural competence, and organizational resilience.

She provides training and facilitation in The Great Reconnection™ and Consulting, helping individuals and teams cultivate vibrant, purposeful, and liberated lives and cultures.

The Great Reconnection™ Coaching is more than just a coaching method—it’s a transformative pathway designed to help you reclaim YOU and step into your authentic power. Through this process, you’ll align with your deepest self, unshackled from the weight of external pressures and societal expectations.

In this episode, Jess and Suzanne discuss:

Being in a "trust recession" and why authentic online sharing builds the kind of connection that leads to real business relationships. Suzanne shares why vulnerability paired with a pathway forward is what moves people to reach out.

How Suzanne launched her podcast in May 2024 for the sheer fun of it and has already reached 35 countries and 2,600 downloads, interviewing guests weekly with a monthly wisdom drop segment called Wisdom Drops.

The unique pre-interview ritual Suzanne uses with every guest: a centering breath, a moment of presence, and an intention set together before recording begins. Jess shares why this was unlike anything she has experienced in hundreds of podcast appearances.

Why there is no amount of strategy and tactics that will sustainably grow your business if your nervous system is dysregulated, and what it looks like to build a culture that is expansive rather than driven by pressure and burnout.

Suzanne's 50-year evolution as a coach, from organizational development and team leadership to somatic work at the Strozzi Institute, to nervous system resets with a literal massage table in her office.

Research Suzanne is now pursuing after discovering that leaders are spending 60 to 85 percent of their day in disconnection and often cannot identify their own signal to reconnect.

Connect with Suzanne Roberts at https://unifyingsolutions.com/

Book your Discovery Call with Jess at https://interviewconnections.com/call