Behind The Business

Most sales conversations don’t fail because the salesperson didn’t pitch hard enough. They fail because the conversation became a pitch before anyone really understood the problem.

In part two of the Sales on Purpose mini-series, Cristy Lime and Hiram Skaggs dig into what makes a sales conversation actually convert.

They break down how to open a conversation without immediately selling, why open-ended questions uncover more than a scripted pitch ever will, and how simple questions like “What do you love about it?” or “How do you do this currently?” can reveal what a potential customer actually needs.

Cristy also shares the “pain to paradise” framework she uses to help buyers clarify both the problem they’re experiencing and what solving it would actually look like.

They also tackle the harder parts of selling: knowing when someone isn’t a fit, navigating objections without manipulation, pushing past vague “maybe next quarter” responses, and getting comfortable asking direct questions when something doesn’t add up.

If selling sometimes feels awkward, scripted, or overly aggressive, this conversation offers a much more human approach.

KEY TAKEAWAYS

1. Start with the problem, not your pitch. Your first job is to understand what the other person is dealing with, not prove how much you know.

2. Use open-ended questions to create better conversations. Who, what, when, where, why, and how uncover far more information than questions that can be answered with yes or no.

3. “What do you love about it?” is a powerful sales question. When someone already has a solution, understanding what works can reveal both what matters to them and where gaps still exist.

4. Understand the cost of the problem. A problem becomes meaningful when you understand what it is costing someone financially, operationally, personally, or mentally.

5. Help the buyer describe the desired outcome. Don’t assume what success looks like. Ask them to describe the “paradise” on the other side of the problem.

6. A script should be a checklist, not a railroad track. Know what you need to cover, but allow a real conversation to move naturally.

7. Every conversation needs a clear next step. That could be another meeting, a proposal, waiting until a specific date, or agreeing that you shouldn’t work together.

Learn more about Behind the Business:
https://theoptimizationspecialists.com/podcast

Subscribe or follow Behind the Business for more conversations about the systems, decisions, people, challenges, and lessons behind building and running a business.

Sales has a reputation problem.

For many business owners, selling brings up images of pushy follow-ups, uncomfortable conversations, rejection, and trying to convince someone to buy something they don't really want. But that isn't what good sales is supposed to be.

In Part 1 of this three-part Sales on Purpose mini-series, Cristy Lime sits down with Hiram Skaggs to unpack the mindset and psychology behind successful selling.

Hiram has built his career around sales, sales leadership, and repeatable sales processes and now serves as Chief Technology and Training Officer for Evolve Social Wellness. Together, Cristy and Hiram explore why founders often avoid selling, why the person who builds the product should usually be one of the first people trying to sell it, and why hearing “no” is simply part of the process.

They also dig into the difference between someone who is good at talking and someone who can actually sell, why “Wow, that's cool” isn't necessarily a buying signal, the danger of getting stuck chasing a maybe, and why every sales conversation needs an ask.

Most importantly, Hiram offers a different way to think about sales: helping someone understand their options so they can make the best possible decision.

This is Part 1 of 3. The next conversation gets deeper into the sales conversations that actually convert.

KEY TAKEAWAYS

• Sales starts with having something worth buying. A clever idea or impressive product isn't enough if customers don't see it solving a problem they care about.

• Your customer's perception is your reality. If the market doesn't understand the value, telling people they're wrong won't fix the problem. You may need to change the message, offer, or solution.

• Founders shouldn't outsource sales too early. Early sales conversations reveal what customers actually value, where they hesitate, and what needs to change.

• “That's cool” isn't a buying signal. Interest in what you've created and willingness to pay for it are two very different things.

• A clear no is better than an indefinite maybe. Don't let a small number of unresolved opportunities consume the time and mental energy that should go toward finding more prospects.

• Good salespeople actually make the ask. Strong relationships and good conversations matter, but every sales interaction should have a clear next step.

• Sales should help buyers make better decisions. The goal isn't to pressure someone into buying. It's to educate them, understand the problem, and help them determine whether your solution is the right fit.

Learn more about Behind the Business:
https://theoptimizationspecialists.com/podcast

Subscribe or follow Behind the Business for more conversations about what really happens behind the scenes of building and growing a business: the systems, decisions, people, mistakes, and lessons that make it work.

At some point, a growing business can become the thing that starts running its owner.

Brian Wirtz knows that transition well. A retired Marine and founder of W3 Integrator Arena, Brian works in the world of EOS, helping develop integrators who can become the operational counterpart to an entrepreneurial visionary.

Brian joins Cristy to break down what an integrator actually does, why the best ones need more than operational experience, and why grit, humility, emotional intelligence, and a willingness to grow can matter as much as an impressive résumé.

He also shares how COVID redirected his original plan to build a recruiting business, why narrowing his focus around EOS actually expanded his opportunities, and how his years in the Marine Corps shaped the way he approaches leadership and difficult conversations.

The conversation also gets practical about when a fractional integrator makes sense, what that person should actually be doing with their limited time, and two mistakes owners can make when evaluating someone for the integrator seat.

If your business is reaching the point where one person can no longer hold everything together, this conversation offers a useful look at what the next layer of leadership can look like.

Key Takeaways

• A growing business eventually needs more leadership capacity than one entrepreneur can provide. The integrator is designed to complement the visionary by helping drive execution, accountability, management, and results.

• Grit and humility can matter more than a perfect résumé. Brian looks for people who have experienced both wins and setbacks and are willing to identify and develop their gaps.

• Emotional intelligence is critical for operational leadership. Integrators have to manage people, navigate communication challenges, build teams, and handle difficult conversations.

• Narrowing your niche can make your positioning stronger, not weaker. Brian found more leverage by specializing in EOS instead of remaining a generic fractional COO.

• Your highest and best use can change as your business evolves. Brian discovered that doing integrator work helped reveal that his longer-term strength is developing content, coaching others, building culture, and training the next generation of integrators.

• Fractional leadership should focus on leverage, not task execution. Limited time is best spent on decisions, leadership, accountability, meetings, and helping other leaders perform when the fractional integrator isn't present.

• Be careful of both false negatives and false positives when hiring. Someone struggling may simply need better scope or development, while an impressive executive may have the experience but not the willingness to embrace the operating system your company has chosen.

What happens when your business is growing, but the life you're building starts falling apart?

Kyle Pertuis knows that tension firsthand. Before founding Mindfit Coaching, he helped grow a hospitality business from one location to five. But behind that growth were 60- to 80-hour workweeks, a difficult partnership, and the realization that the business was pulling him away from the people and values that mattered most.

In this episode of Behind the Business, Kyle sits down with Cristy Lime to share how that experience changed his approach to entrepreneurship, leadership, and success.

Now nearly 17 years into building Mindfit Coaching, Kyle helps leaders and organizations turn leadership development into measurable, sustainable behavior change. He explains why completing leadership training doesn't necessarily mean anyone is leading differently, how growth exposes leadership weaknesses, and why building the right systems is essential as teams expand.

Kyle also shares his practical 5-5-30 business model, how he balances structure with flexibility, and why AI should support human development rather than replace it.

At the heart of the conversation is a question every business owner should consider: Is the business you're building actually supporting the life you want to live?

If you've ever questioned whether more growth is worth the personal cost, this conversation offers a different way to think about success.

CONNECT WITH KYLE PERTUIS

Mindfit Coaching: https://mindfitcoaching.com
Inspired Action Leadership: Search for Inspired Action Leadership
Email: [email protected]
Podcast: Inspired Action, the Leadership Forecast Podcast

Learn more about Behind the Business:
https://theoptimizationspecialists.com/podcast

Subscribe to Behind the Business for more candid conversations with business owners about the decisions, systems, challenges, and lessons behind building successful businesses.

Most business owners don't celebrate hitting a plateau. Christian Wright does.

Christian is the owner of High Tide Pest Control, a Charleston-area family business that's reached an important stage of growth: demand is there, the schedule is filling up, and Christian knows the business can't continue growing with him doing everything himself.

But instead of squeezing more appointments into every day, Christian is deliberately protecting the thing that helped High Tide grow in the first place: the customer experience.

In this conversation with Cristy Lime, Christian shares why he limits his schedule to roughly eight to ten stops a day, how referrals became a major source of growth, why High Tide services customers more frequently than the traditional pest-control model, and how he's preparing to make his first technician hire.

They also get into the transition from operator to owner, the systems Christian is building before the next growth spurt, and why he sees his current plateau as an opportunity rather than a problem.

It's a practical conversation about what happens when a small service business starts outgrowing its owner — and how to scale without losing what made the business work in the first place.

Key Takeaways

• Capacity is a strategic choice. Christian caps his day at roughly eight to ten stops because maximizing appointments would reduce the time available to serve each customer well.
• Build around your environment, not just industry convention. High Tide uses roughly 60-day service intervals because Christian believes Charleston's heat, humidity, and rain require a different approach than the standard quarterly model.
• Fast response can be a competitive advantage. High Tide intentionally leaves room in the schedule for unexpected customer issues rather than booking every available minute.
• Your first hires have to carry the standard, not just perform the task. Christian wants future technicians certified and capable of educating customers, not simply applying treatments.
• Growth eventually exposes owner dependency. Christian recognizes that High Tide has reached a point where continuing to grow requires adding capacity beyond himself.
• A plateau can be productive. Slower periods create an opportunity to strengthen systems and prepare before the next growth cycle.
• The goal isn't simply getting Christian out of the field. His long-term vision is a company that can operate independently while preserving High Tide's quality standard and giving him more time with his family.

Gabe Garcia started with a camera, a love for people, and a problem: the creative community he wanted didn’t exist.

So he helped build it.

What began as informal photo walks eventually became SA Creatives, a thriving San Antonio creative community. At the same time, Gabe was building Summit Creative, his agency. The two grew side by side—sometimes supporting each other and sometimes competing for the same time, money, and attention.

In this episode of Behind the Business, Cristy Lime talks with Gabe about what actually happened behind that growth.

They unpack the moment community-building had to become more operational, why sponsorships and KPIs changed the way Gabe thought about SA Creatives, how Summit Creative began funding the “fun” business, and why Gabe eventually had to step away from doing so much creative work himself.

Gabe also shares how AI and automation have radically changed the way Summit operates—from client reporting and monday.com workflows to a custom client dashboard he says would once have cost tens of thousands of dollars to build.

But underneath all the technology is a very human philosophy: build relationships, listen closely, give generously, create systems that make room for talented people, and remember there is still a person behind every business.

A creative business still needs structure behind the scenes.

Rob Keller has spent roughly 15 years working in video, beginning with a middle-school camera project before eventually turning videography, brand storytelling, and strategy into a full-time business. But becoming great at the creative work was only part of the challenge. Running the business required a completely different set of skills.

Rob joins Jon Clark to talk about the systems that helped turn a creative operation into a more organized business, including why he stopped copying processes built for $100 million companies, how working with his wife changed the way they operate, and why something as simple as a shared Apple Note became an important part of their weekly workflow.

They also dig into video strategy, building a content funnel, using Asana and Frame.io to manage client production, setting deadlines that create accountability on both sides of a project, and planning around travel and production work.

Rob also explains why business owners should “advertise what they want to attract” and shares his approach to building a personal network of mentors instead of relying on one person for every answer.

The systems that helped you build a business aren’t necessarily the ones that will help you scale it.

Season 4 marks a new chapter for the podcast. What was formerly the Overnight Success Podcast is now Behind the Business, with a sharper focus on what actually makes businesses work: the systems, processes, people, technology, decisions, and growing pains happening behind the scenes.

In this season kickoff, Jon Clark and Cristy Lime share why the show is changing and pull back the curtain on changes happening inside The Optimization Specialists as well.

They discuss what happens when growth exposes weaknesses in existing systems, why better positioning changed the conversations they were having with business owners, and how operational problems can quietly create revenue leaks even when leads are coming in.

Jon and Cristy also explore how they’re using AI to support the sales process, why they’re building custom “command centers” on top of existing software, and the importance of designing technology around how people actually work.

It’s a look at where Behind the Business is headed—and why understanding what happens behind the scenes may be more useful than another polished success story.

What actually separates businesses that scale from those that stall?

In this Season 3 finale, Jon and Cristy sit down to break down the real patterns behind the “overnight success” stories featured this season—and what founders often miss when trying to grow.

After dozens of conversations with founders across industries, one thing became clear: success isn’t random—it’s built on systems, execution, and the ability to evolve before chaos takes over.

Jon and Cristy unpack:

• The hidden growth ceilings every business hits
• Why founders become the bottleneck (and how to fix it)
• The difference between adding people vs. improving systems
• How AI is actually changing operations—not replacing them
• And what’s next for the podcast in Season 4

They also pull back the curtain on how they’ve implemented AI into their own workflows—turning conversations into actionable systems and accelerating decision-making across their business.

If you're building, scaling, or feeling stuck in your business—this episode will change how you think about growth.

👉 Subscribe, follow along, and get ready for a deeper dive into systems, AI, and real scalability in Season 4.

Chapters

00:00 – Season 3 Finale KickoffJon and Cristy introduce the episode and set the stage for a different kind of conversation—recapping lessons and looking ahead.

01:00 – The Patterns Behind “Overnight Success”
Why every founder story was different—but the underlying themes were the same.

02:30 – Time, Patience & The Myth of Instant Growth
Why success takes longer than expected—even in a fast-moving, AI-driven world.

04:30 – Growth Creates New Problems
How scaling introduces complexity, pressure, and unexpected challenges.

06:00 – People vs. Systems: What Actually Scales?
The ongoing tension between hiring and building better systems.

07:30 – The Founder Bottleneck Problem
Why founders often become the biggest constraint to growth—and how to fix it.

09:30 – Getting Out of Your Own Way
Delegation, SOPs, and stepping into the true CEO role.

10:45 – Mindset, Clarity & Decision-Making
Why most founders aren’t stuck—they’re just hesitant to act.

12:00 – Breaking Through Analysis Paralysis
The power of taking action and iterating instead of overthinking.

13:15 – Building Systems That Actually Work
How intentional systems (like EOS-style frameworks) drive scalability.

15:30 – Execution Over Everything
Why consistent action beats perfect strategy every time.

17:30 – Shifting Toward the Future of the Podcast
Transitioning from founder stories to deeper operational insights.

18:30 – How AI is Changing Business Operations
Moving beyond content generation into real workflow integration.

19:45 – Real Example: AI-Powered Discovery Calls
How Jon and Cristy use AI to turn conversations into actionable insights and faster proposals.

22:00 – AI Isn’t Replacing Jobs—It’s Enhancing Them
Reframing the narrative around AI in business.

24:00 – AI for Reporting & Decision-Making
How AI is transforming dashboards into actionable insights.

26:30 – Why Businesses Need to Adapt Now
The importance of learning and experimenting with AI.

28:30 – What’s Next for Season 4
A preview of the shift toward systems, workflows, and practical AI use cases.

31:00 – Final Thoughts & Wrap-Up
Closing reflections and what listeners can expect moving forward.

What does it really take to scale a business without creating more chaos?

In this episode, Hiram Skaggs of Evolve Social Wellness joins Jon Clark for a real conversation about growth, systems, and what happens behind the scenes when a successful single location starts expanding into a franchise model.

This episode explores how Evolve measured what was working, simplified operations, reduced friction for staff and franchisees, and built systems that could actually be adopted in the real world. Hiram also shares a refreshing perspective on sales as education, why integrity matters in long-term growth, and how better systems create better customer experiences.

Hiram serves as the Chief Technology and Training Officer for Evolve Social Wellness, where he helps franchisees improve performance, implement scalable systems, and create a more accessible wellness experience for more people.

For anyone building a franchise, leading a growing team, or trying to scale without losing the human side of the business, this conversation delivers practical insight with real depth.

Subscribe for more conversations on business growth, systems, and building companies that last.