Evolving Your Workplace

One in four employees is seriously mentally distressed — and it's rarely about the person; it's about the workplace itself!

This conversation dives into why workplace mental health is quietly collapsing, the hidden cost of untrained managers, and the simple systems — from tracked airtime to two-minute check-ins — that can turn a toxic culture around.

We discussed:

◼ Why depression rates tripled during the pandemic and never came back down

◼ How one Gallup number predicts 70% of your team's engagement

◼ The two simple questions that instantly rebuild trust with your team

◼ Why fixing individuals is solving for the completely wrong problem

◼ How one CEO's 30,000 handwritten notes turned a failing company around

🎙️ Host: Carol Schultz

LinkedIn: https://www.linkedin.com/in/carolbschultz/

Vertical Elevation: https://www.linkedin.com/company/vertical-elevation/

🎤 Guest: Laura Putnam

LinkedIn: https://www.linkedin.com/in/lauraputnam/

Motion Infusion: https://www.linkedin.com/company/various-schools-and-organizations/

🎧 Find us

YouTube: https://www.youtube.com/@EvolvingYourWorkplace

Spotify: https://open.spotify.com/show/72jbAC9Hk4P0EH9wxW1vy4?si=b0eab40cecc343e3

Apple Podcasts: https://podcasts.apple.com/us/podcast/evolving-your-workplace/id1562180951

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

A company with no staff, no payroll, and no traditional org chart — just AI models, subscriptions, and 300 hand-picked consultants!

How a business scales with zero employees: AI-powered prospecting, brutal consultant vetting, deliberately thin 33% margins, virtual CIOs delivering 400% ROI, and why vendors are keeping the AI savings their clients deserve.

We discussed: ◼ Why a firm deliberately keeps just 33% margin while competitors keep 60% ◼ How interviewing 800 consultants during COVID built a 300-person network ◼ The single interview question that exposes technologists who can't think like executives ◼ Why fractional leadership commonly delivers 400% ROI in the mid-market ◼ The "AI dividend" your suppliers are banking as margin instead of passing to you

🎙️ Host: Carol Schultz

LinkedIn: https://www.linkedin.com/in/carolbschultz/

Vertical Elevation: https://www.linkedin.com/company/vertical-elevation/

🎤 Guest: Jeff Roberts

LinkedIn: https://www.linkedin.com/in/robertsjeff/

Innovation Vista: https://www.linkedin.com/company/innovationvista/

🎧 Find us YouTube: https://www.youtube.com/@EvolvingYourWorkplace

Spotify: https://open.spotify.com/show/72jbAC9Hk4P0EH9wxW1vy4?si=b0eab40cecc343e3

Apple Podcasts: https://podcasts.apple.com/us/podcast/evolving-your-workplace/id1562180951

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

"Businesses don't fail because of what they do. They fail because of everything else." – Michael Sakata

In this week’s episode, Carol Schultz sits down with Michael Sakata, President & CEO of the Maryland Transportation Builders and Materials Association (MTBMA), to discuss how federal policy decisions are impacting small businesses, contractors, and transportation firms across the country. The conversation centers on recent changes to disadvantaged business enterprise (DBE) programs, the uncertainty created by shifting regulations, and what business owners can do when the rules suddenly change.

Michael explains how the removal of race-based criteria from DBE certification has created new questions for businesses that have relied on these programs for decades. Rather than focusing on politics, the discussion explores the practical realities facing contractors, engineers, and small business owners as they navigate evolving requirements, funding concerns, and changing government priorities. Carol and Michael also dive into the role of relationships in business success, why networking matters more than ever, and how organizations can remain resilient during periods of uncertainty.

The episode closes with lessons on leadership, communication, membership growth, and the importance of staying engaged with industry associations and policymakers. Michael shares how MTBMA has more than doubled its membership under his leadership and why consistent communication remains one of the most important drivers of retention and long-term success.

• Federal policy changes can create significant uncertainty for small businesses.
• Changes to DBE certification programs are forcing many companies to reassess their strategy.
• Business owners should focus on impact rather than politics when evaluating policy decisions.
• Strong relationships often matter more than formal programs or certifications.
• Companies that stay engaged with industry groups are better positioned to adapt to change.
• Infrastructure remains one of the few areas that continues to receive bipartisan support.
• Consistency and predictability are critical for business growth and planning.
• Communication is one of the strongest drivers of member, customer, and employee retention.
• Successful organizations create value through networking, advocacy, and education.
• Leaders must focus on what they can control rather than reacting to every external change.
• Trade associations can give businesses a stronger collective voice with policymakers.
• Growth often comes from listening closely to members, customers, and stakeholders.

00:00 Intro: How federal decisions impact everyday businesses

01:05 Michael Sakata's role and the mission of MTBMA

02:19 Changes to disadvantaged business enterprise (DBE) programs

03:40 What the new certification landscape means for small businesses

05:10 Why uncertainty creates challenges for business owners

06:22 Relationship-building vs. government-supported opportunities

08:19 The original purpose of DBE programs and ongoing debates

10:30 Advice for businesses navigating regulatory changes

11:44 How disadvantaged business status has changed

13:38 Political perspectives and the impact on transportation businesses

15:04 Why businesses need consistency to thrive

17:35 What business owners can do when policies change

18:04 Infrastructure as a rare bipartisan issue

19:45 Michael's career journey into transportation advocacy

20:36 Legislative wins and improving transportation safety

22:14 Why trade associations can influence policy effectively

23:54 The secret behind a 96%+ membership retention rate

26:38 Creating value for members through networking and advocacy

30:28 Collaboration between transportation organizations across states

32:21 Managing change instead of being controlled by it

34:02 How MTBMA more than doubled its membership

36:10 Final thoughts and closing remarks

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

In this week's episode, Carol Schultz sits down with Beth Goff- McMillan, CEO of SKG and founder/CEO of FOLIO, to dig into how office design has completely transformed since COVID—and why most companies are stuck in what Beth calls a "vortex of confusion" about what their workspace should even be.

Beth shares 30 years of industry insight on the shift from rigid cubicle layouts to fully open offices to today's hybrid chaos, and explains why the real question leaders need to ask isn't "what furniture do we buy" but "why do we even need an office." They get into what makes employees actually want to come back in (hint: it's not ping pong tables), the most expensive and most overlooked design mistakes companies make, and how a simple employee survey can save a business tens of thousands of dollars. The episode wraps with a look at FOLIO, the tech platform Beth built to drag a notoriously slow-moving industry into the SaaS era.

Takeaways

1. Most leaders are stuck on "what" to put in their office instead of asking "why" they need an office at all.
2. Return-to-office policies alone don't drive engagement or productivity—you need clear KPIs tied to purpose.
3. Employee surveys (before AND after a redesign) can prevent massively expensive, unused investments.
4. Noise and acoustics should be the #1 design priority post-COVID—people need more visual/sound barriers, not fewer.
5. Gimmicks like ping pong and shuffleboard tables rarely get used and often signal a lack of real design intent.
6. Storage and file cabinets are some of the most expensive—and most unnecessary—line items in office design.
7. "Resi-mercial" design (home-like textures, plants, varied seating) makes employees feel more connected and productive.
8. Large conference rooms often go underused—flexible lounge spaces can replace them entirely.
9. Workplace design decisions involve far more stakeholders than people expect: C-suite, facilities, HR, IT, and legal.
10. The furniture/design industry is still behind on technology—and AI-driven tools are starting to close that gap.

Chapters

00:00 Intro: How office spaces have transformed since COVID

01:49 What SKG actually does (workplace strategy, design, furniture procurement)

03:10 30 years of office evolution: from Dilbert cubicles to fully open floors

05:33 The "vortex of confusion"—why nobody has a playbook anymore

07:07 Shifting the conversation from "what" to "why"

09:24 Three things every workspace needs to succeed post-COVID

11:29 "I wanted to earn their commute"—how design changed employee behavior

12:48 Why noise and acoustics should be priority #1

14:21 Dress codes, client expectations, and reading the room

16:17 Two things to leave out of your office (gimmicks & excess storage)

18:41 Bringing "resi-mercial" design into the workplace

23:11 Who SKG actually meets with—from CEOs to facilities to legal

25:19 The survey that saved a client from a costly coffee bar mistake

28:21 Redesigning SKG's own HQ: what worked and what didn't

33:04 The privacy/acoustics fail—and how they fixed it

36:47 Why Beth joined SKG and what keeps her there 11 years later

39:03 Folio: building the first SaaS tool for the furniture dealership industry

43:11 Current bottlenecks: training talent in a fast-changing industry

45:00 Final thoughts

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

“Lead yourself before you lead others.” – Jane Monroe

In this week’s episode, Carol Schultz sits down with Jane Monroe, founder of Embrace the Grape Beverage Catering, to explore one of the most overlooked leadership skills: self-awareness. What started as a conversation about leadership quickly became a masterclass on blind spots, delegation, personal growth, and building teams that can lead themselves.

Jane shares the unexpected story of how a bride’s wedding problem led her to launch a completely new business during the 2008 financial crisis. From there, she introduces her framework for leadership cohesion, breaking down the four versions of ourselves—the known self, blind self, hidden self, and mystery self—and explains how understanding each one can transform the way we lead.

Carol and Jane discuss why many leaders struggle with control, how delegation creates stronger organizations, and why hiring people who compensate for your weaknesses is a competitive advantage. They also dive into trust, employee empowerment, succession planning, and the importance of balancing logic with intuition to become a more whole-brained leader.

The episode closes with practical lessons for leaders looking to build high-performing teams, uncover their blind spots, and create workplaces where accountability starts from within.

Takeaways

• Self-awareness is the foundation of effective leadership.

• Blind spots can limit growth until someone helps uncover them.

• Great leaders learn to lead themselves before leading others.

• Growth happens when you step outside your comfort zone.

• Delegation allows leaders to focus on their strengths.

• Hiring for your weaknesses creates stronger teams.

• Employees perform better when given ownership instead of micromanagement.

• Different perspectives often produce better outcomes than one leader working alone.

• Strong cultures are built on trust, communication, and accountability.

• Encouraging employees to “manage up” creates healthier organizations.

• Leadership exists at every level—not just in management positions.

• Balancing emotional intelligence with logical thinking leads to better decisions.

Chapters

00:00 Intro: Why self-awareness separates great leaders from everyone else

01:11 Meet Jane Monroe & the story behind Embrace the Grape

02:19 The bride who accidentally created a business opportunity

04:29 Turning blind spots into entrepreneurial breakthroughs

07:01 The four selves: known, blind, hidden, and mystery

09:37 Why growth requires getting comfortable being uncomfortable

11:54 Leading yourself before leading others

13:51 A powerful framework for humility and leadership

15:58 Learning to let go: delegation and control

17:03 Hiring for your weaknesses instead of your strengths

18:13 Diversity of thought and avoiding groupthink

19:15 How delegation unlocks team growth

20:05 Empowering employees through trust and ownership

21:41 Giving people opportunities to exceed expectations

22:41 When employees redesign your plans for the better

23:09 Managing up: why leaders need feedback too

24:05 Building a culture of accountability with part-time teams

25:38 Hiring experienced professionals and maintaining low turnover

26:39 Supporting employees through major life transitions

27:35 Succession planning when family doesn't want the business

29:12 Whole-brain leadership: balancing emotion and logic

31:38 Final thoughts & closing remarks

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

"Don't ask what I would do. Ask what's best for the patient." – Amit Gir, MD

In this week's episode, Carol Schultz sits down with Amit Gir — physician, entrepreneur, and CEO of Phox Health — to dig into one of the most underrated leadership challenges: creating a culture where employees take real ownership, instead of waiting to be told what to do. Amit shares how he built a remote-first healthcare logistics company across 12 states and two continents, almost entirely by learning when to let go — and who to let run.

Amit explains why the best leaders learn every inch of the business before delegating it, how to tell the difference between micro-feedback and micromanagement, and why he has a strict rule of never taking credit for a good idea. They also get into the messier side of leadership — what happens when someone doesn't show ownership, how fear-based cultures quietly kill companies, and why giving employees "the rope" is the only way to find out who will climb and who won't. The episode closes with Amit's core belief: when the mission is bigger than the manager, ownership stops being a personality trait and starts becoming company culture.

Takeaways

1. Learn the business deeply before you hand it off — you can't manage what you don't understand.
2. Hire people who can teach you something, not just execute your ideas.
3. The best hires are the ones who eventually do the job better than you could.
4. Passing ownership means giving a rough playbook — then getting out of the way.
5. Never own a good idea. Only own the bad outcomes.
6. Micro-feedback is about speed, not control — the faster the feedback, the faster the growth.
7. Fear-based leadership creates silence, not performance.
8. When the mission drives decisions — not the founder — ownership becomes instinct.
9. A culture of feedback has to be modeled by the CEO first, every single day.
10. Remote teams can scale — but only when built with intention, not just cost savings.

Chapters

00:01 Intro: The real cost of employees who wait for permission

01:27 What Fox Health does and why it exists

02:22 From medical school to startup — Amit's founder origin story

05:20 What ownership actually looks like on Amit's team

08:35 The Atlanta hire — no resume, no healthcare background, full ownership

10:31 Giving employees the rope — risk, trust, and letting go

11:13 Why you should hire people who can replace you

12:24 The one instruction Amit gives every new hire

13:02 When ownership doesn't show up — and how to act fast

14:26 The credit rule: he never owns a good idea

15:06 Micro-feedback vs. micromanagement — where the line is

17:40 Leading by example when no one's watching

18:12 How to build a culture of feedback from the top down

19:21 Love vs. fear — which one actually builds better teams

22:08 Running a global remote team across the US, India, and Scotland

24:52 Gender dynamics in a global workforce

25:10 Why Fox Health ended up 50%+ female — by accident

28:46 Turning time zone gaps into a competitive advantage

32:35 Final thoughts: hire with purpose, not just for price

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

"If you don't plan for where your customers are moving, you're not going to have a business." – Melinda Powelson

In this week's episode, Carol sits down with Melinda Powelson, CEO of Match Engine, to explore what brand survival really looks like when the industry you built your business on starts disappearing beneath your feet. From a Denver recycling company founded just after the first Earth Day to one of the earliest lead generation platforms on the internet, Match Engine's story is a masterclass in knowing when to pivot — and having the courage to actually do it.

Melinda breaks down why so many businesses get left behind when industries shift, why watching trends and data is non-negotiable for long-term survival, and how her company is already preparing for the decline of paper shredding by moving into medical waste, electronic recycling, and AI-powered sales tools. Carol and Melinda also dig into the tension between embracing AI and protecting the human touch in customer relationships, why office paper shipments have dropped 36% since COVID, and what the Yellow Pages and Kodak teach us about ignoring the writing on the wall.

The conversation also covers family business succession, founder syndrome, why 70–80% of family-run businesses fail between the first and second generation, the real difference between wanting something and committing to it, and why hiring people with a tolerance for change may be the single most important thing a leader can do right now.

Takeaways

• Businesses that fail to track industry trends risk becoming the next Kodak or Yellow Pages.
• Office paper shipments in the U.S. have dropped 36% since COVID — document-heavy industries must adapt.
• Medical waste and electronic recycling are growth verticals as paper shredding declines.
• AI search is reshaping lead generation, and businesses that ignore it will fall behind.
• Using AI to enhance your team's performance is fundamentally different from using it to replace people.
• Customers in certain demographics still strongly prefer speaking to a human over a bot.
• Family business succession fails 70–80% of the time between the first and second generation.
• The baton handoff only works when the original founder is willing to fully let go.
• Commitment — not just wanting — is what separates entrepreneurs who make it from those who don't.
• Hiring for change tolerance is as important as hiring for skill.
• Women leaders may have a natural advantage in delegation and trust-based team building.
• A subscription revenue model offers stability that a pure lead-generation model cannot.

Chapters

00:00 Intro: Office paper is down 36% — is your business paying attention?

01:09 Introducing Melinda Powelson and Match Engine

01:58 How it all started: Tri Our Recycling and the first Earth Day

02:34 Building a website in 1995 before Google existed

03:38 The birth of Shred Nations and early lead generation

04:09 Why the internet business was losing $20K a month — and how they fixed it

04:46 The fundamentals of pivoting: platform economics and customer value

06:19 Advice for leaders who know they're falling behind

07:09 "Fish where the fish are" — and the fish have moved

07:32 Why AI search is the next frontier for lead generation

09:37 Defining risk: changing what works today for an uncertain tomorrow

10:26 Match Engine's AI philosophy: enhance people, don't replace them

11:31 Why boomers won't talk to bots — and why that matters

12:28 Salesforce's AI hiring reversal as a cautionary tale

13:12 The value of people and hiring for change tolerance

13:57 How Melinda entered the family business (she was an English major)

15:09 The gradual baton handoff from father to daughter

16:16 Why family business succession fails 70–80% of the time

17:16 The personal commitment that made the difference

18:48 Eight years as CEO — and the three and a half that changed everything

19:23 Why CEOs need peer groups — and how hard they are to find

22:11 Founder syndrome and why women may be better at letting go

24:24 Planning your own exit from day one

26:19 Building a new team and saying hard goodbyes

27:27 Vision first, then team, then adapt

28:26 Industry shift: paper down, medical waste and e-recycling up

30:04 The Yellow Pages and Kodak lesson

30:56 Revenue targets and the move toward a subscription model

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

“People don’t buy from logos—they buy from people.” – Rachel Gogos

In this week’s episode, Carol Schultz sits down with Rachel Gogos, founder and director of strategy at brandiD, to unpack what it really takes to stand out in a world where nearly every business feels interchangeable. From AI-generated websites and generic branding to personal positioning and founder-led marketing, Rachel explains why businesses that feel human are winning trust while “commodity brands” are getting ignored.

Rachel breaks down why so many companies fail to connect online despite spending money on websites, SEO, and content. She explains why founders themselves are often the biggest differentiator in a business, why audiences are becoming increasingly skeptical of AI-generated content, and how businesses can build stronger relationships by making customers feel seen instead of constantly talking about themselves. Carol and Rachel also discuss the growing importance of authenticity, messaging clarity, customer psychology, and why businesses must stop relying on shortcuts if they want long-term growth.

The conversation also explores personal branding myths, why introverts can still build powerful brands, how LinkedIn differs from other platforms, and why consistency across websites, podcasts, social media, PR, and messaging is essential for modern businesses trying to survive in crowded markets.

• The founder is often the strongest differentiator in a business.
• Customers increasingly want authentic, human brands.
• AI-generated branding can feel emotionally empty and mechanical.
• Businesses fail when they focus too much on themselves instead of customer pain points.
• Personal branding is not just for extroverts or influencers.
• Strong messaging starts with understanding the customer first.
• Websites alone don’t generate growth—marketing and positioning matter.
• Consistency across platforms builds stronger trust and authority.
• Many businesses abandon marketing strategies too early.
• SEO, copywriting, and brand positioning all work together as one ecosystem.
• Founder-led content performs especially well on platforms like LinkedIn.
• Differentiation comes from understanding what competitors are missing.

00:00 Intro: Standing out in a commodity-driven world

02:35 Why founders are the biggest differentiator

03:37 Rachel Gogos on building brandiD and helping businesses grow online

04:29 Why outdated websites and weak messaging hurt brands

05:19 Budget mistakes businesses make early on

06:29 The problem with AI-generated websites and branding

07:50 Why authentic brands build stronger trust

08:12 Why founders should become the face of the business

10:38 Branding mistakes companies make too early

11:07 Why customer-focused messaging matters

11:28 The danger of constantly changing marketing strategies

12:37 Why audiences are getting tired of AI-generated content

13:39 Rachel’s entrepreneurial journey and starting brandiD

15:36 Personal branding vs. business branding

16:26 Why people buy from people

17:45 Combining founder branding with company branding

19:29 Building a full marketing ecosystem around a website

21:58 Word-of-mouth, Google, and personal branding as growth channels

23:25 Why many industries are becoming commoditized

25:53 Carol’s SEO and AEO growth strategy experience

28:02 Finding the right talent in SEO and marketing

31:38 Separating your business from competitors

32:40 How a cigar brand successfully differentiated itself

35:15 Building brand trust through consistency and community

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

In this week’s episode, Carol Schultz sits down with Brent Rempe (President & CEO of First Alliance Credit Union) to unpack what actually drives workplace evolution—and why most companies fail to make their values meaningful. Brent shares how his team redefined their mission, vision, and values after realizing the old ones didn’t resonate, and how simplifying them into something tangible changed the direction of the organization.

Brent explains why having too many values makes them forgettable, how organizations can embed values into hiring and performance systems, and why alignment matters more than raw output. They explore how behavioral interviews reveal real character, why pairing HR with hiring managers improves decision-making, and how growth can expose weaknesses inside a team. The conversation also touches on leadership realities—like imposter syndrome—and why purpose and storytelling are critical to keeping employees engaged. The episode closes with a practical look at how companies can create workplaces where people feel connected to the impact of their work, not just the job itself.

• Mission, vision, and values only work if they are simple and actionable
• Too many values make culture harder to understand and apply
• Values should be embedded into hiring, performance, and daily decisions
• Behavioral interviews help uncover genuine alignment—not rehearsed answers
• HR involvement improves hiring consistency and reduces bias
• Growth without alignment can create internal friction
• Employees stay engaged when they feel their work has real impact
• Storytelling helps teams connect to purpose and meaning
• Even experienced leaders deal with imposter syndrome
• Strong culture creates momentum, not just compliance

00:03 Intro: What it means to evolve a workplace

04:13 Rethinking mission, vision, and values

05:14 Why simplicity in values matters

07:33 The three core tools: mission, vision, values

08:17 Embedding values into hiring and performance

09:10 How to interview for alignment

10:28 The role of HR in better hiring decisions

15:58 Defining the ideal member and growth focus

18:05 Looking beyond credit scores: human-centered decisions

20:26 Growth challenges and team development

26:19 Imposter syndrome among leaders

31:25 Purpose, storytelling, and employee motivation

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!

“If you’re the linchpin… it gets really hard.” – Greg Moore

In this week’s episode, Carol Schultz sits down with Greg Moore (Founder & CEO of Fit3D and WAIR) to unpack the reality of running two companies at the same time—and whether it’s actually possible to grow both without becoming the bottleneck.

Greg explains how his businesses operate under one umbrella but function as completely separate entities, each demanding different teams, strategies, and attention. He breaks down the core challenge founders face when splitting time: growth slows the moment you become the center of every decision (“linchpin”). The conversation explores why building systems, delegating responsibility, and structuring time intentionally are critical if you want both companies to scale.

They also dive into the trade-offs most founders ignore—how dividing attention can limit growth, why one company could flourish faster with full focus, and why Greg admits he wouldn’t start two companies at once again unless they were properly capitalized. The episode closes with a practical look at how he manages both today through time blocking, communication systems, and separating strategy from execution roles.

• Splitting time between companies is possible—but not without trade-offs
• Growth stalls when the founder becomes the operational bottleneck
• Systems and delegation are essential to avoid being the linchpin
• One company can often grow faster with undivided focus
• Running two businesses requires structured time blocks and communication
• Founder-led roles (like sales) make splitting time even harder
• Proper capitalization changes everything when managing multiple companies
• Without systems, you’re managing chaos—not scaling businesses

00:06:29 The core challenge: leading two companies under one umbrella

00:06:57 Can you split time without teams competing for attention?

00:07:17 Adapting leadership: companies adjust to limited founder time

00:07:55 The reality: planning, communication, and constant coordination

00:08:13 Why your time is always split—and never enough

00:12:04 Founder lesson: why Greg wouldn’t start two companies again

00:12:44 The linchpin problem—and how it limits growth

00:13:05 When companies depend on each other financially

00:13:21 The 3 conditions required to run multiple companies successfully

00:21:54 Weekly workflow: balancing strategy vs execution across both companies

00:24:07 Working “in” vs working “on” the business

Connect With Host Carol Schultz

Find more information about our host Carol Schultz and her company at Vertical Elevation, LinkedIn, YouTube, and Instagram.

Want to be our next guest expert? Email [email protected] with your information.

And of course, click "follow" to stay up-to-date on new episodes and leave an honest review/rating letting us know what you thought!