Episode 83: Build the Business, Don’t Break the People
Episode Description:
In this episode of Don’t Waste the Chaos, host Kerri Roberts welcomes Emily Holdman, Managing Director at Permanent Equity a Missouri-based private equity firm investing 30-year committed capital into businesses that care deeply about what happens next.
This isn’t your typical business conversation.
Emily reveals how she leads during seasons of complexity without compromising care prioritizing clarity over comfort, long-term value over short-term wins, and people over posturing. From redefining leadership and decision-making to navigating motherhood, burnout, and contentment, this conversation is a rare blend of strategic thinking and human honesty. Emily currently serves on the boards of Ace Fence, Presidential Pools & Spas, Selective Search, Rylee + Cru, and Ad Advance. She’s an unapologetic optimist about the power of small-but-strong companies to transform lives and communities and her track record proves it.
Whether you’re a founder, executive, or someone rethinking the kind of leader you want to be, this episode will challenge and inspire you to build the business without breaking the people.
Tune into hear:
Clarity Is Kindness Sugarcoating change causes harm. Emily shares how transparency and honesty even when uncomfortable are the most respectful ways to lead.
Do No Harm ≠ Do Nothing The “do no harm” philosophy at Permanent Equity is about walking in with empathy, not apathy. It's about choosing intentional, people-first improvement instead of rushed overhaul.
Real Leadership Requires Unlearning Emily gets raw about her early years of hyper-productivity, control, and fear, and how she learned to trust others, delegate, and lead collaboratively.
Your Team Deserves Autonomy, Not Artificial Safety Rather than coddling employees through transitions, empower them with authorship, responsibility, and agency. It’s more honest and more effective.
Contentment Isn’t Laziness - It’s Maturity After years of chasing productivity and financial "security," Emily shares the surprising power of margin, presence, and letting go of scarcity.
Mentioned in this Episode:
Permanent Equity https://www.permanentequity.com/
Emily Holdman – LinkedIn / emilyholdman
The Book of Charlie: Wisdom from the Remarkable American Life of a 109-Year-Old Man By David Von Drehle https://www.amazon.com/Book-Charlie-W...
Don’t Waste the Chaos – Full Podcast Library https://kerrimroberts.com/dontwasteth...
HR Easy Button Book Series – Salt & Light Advisors https://www.saltandlightadvisors.com/...
Kerri M. Roberts – Official Website https://www.kerriroberts.com/
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Full Transcript
Kerri Roberts (00:01):
Welcome back to another episode of Don’t Waste the Chaos, the podcast where we pull back the curtain on business, leadership, and the beautiful mess of becoming who we are made to be. I’m your host, Kerri Roberts, and today’s conversation is one I’ve been looking forward to for quite a while.
Emily Holdman is the Managing Director at Permanent Equity, a Missouri-based private equity firm known for its refreshing long-term perspective and values-first approach. She leads with equal parts conviction and care, overseeing investments and walking alongside companies long after the deal is done.
She currently serves on the boards of Ace Fence, Presidential Pool and Spas, Selective Search, Riley and Crew, and Ad Advance. What stands out most is her belief in the power of small but strong businesses to transform communities and lives.
In this episode, we talk about leading through complexity with clarity, navigating high-stakes seasons with people-first wisdom, and what it truly looks like to do no harm in business and beyond. We’ll also discuss rhythms that keep her grounded, what she’s had to unlearn in leadership, and how chaos has sometimes brought unexpected clarity.
Emily, welcome to the show.
Emily (01:14):
Thanks, so good to see you.
Kerri Roberts (01:16):
Good to see you too. I was trying to think about how long we’ve known each other. I know we co-founded Women in Technology, but I think we met before that.
Emily (01:22):
I think it’s been about 15 years. Your son was a little kid at the time.
Kerri Roberts (01:46):
Yes. Let’s jump right in. Between making big decisions and guiding people through complexity, how would you describe your leadership style on your best days?
Emily (02:04):
It’s about how you enter the room. I don’t sit side-by-side with everyone daily, so I prepare as much as possible while keeping formality minimal. I start with genuine check-ins—sometimes professional, sometimes personal—because I want to understand them as people, not just coworkers.
I’m efficient and focused. We both know why we’re there and what we want to accomplish. I respect their time and avoid unnecessary updates or “performative” explanations. My goal is clarity: mapping where we are now (positive analysis) and where we could be (normative analysis).
Sometimes a 30-minute meeting takes only five, and that’s fine. I prepare thoroughly, address the issue, and move on—while also building relationships. People appreciate that we address “the sticky stuff” directly instead of avoiding it.
Kerri Roberts (04:46):
That’s been my exact experience with you for years. Even today, before we started recording, I said I’d love more time together, but we’re both busy.
Emily (05:07):
I’m not great at small talk for its own sake, but I enjoy knowing what excites people personally and professionally—it helps me understand their motivations. When we’re discussing strategy, I like to talk directly about the issue instead of circling around it. Recognizing everyone as adults and being honest works well.
Kerri Roberts (06:03):
If everyone could just say what they need to say, it would change the business world.
Emily (06:06):
People often make up stories about why someone won’t receive feedback well. My experience is that if you’re not attacking or cornering them, but genuinely trying to understand and improve something, they respond well. Even if the initial reaction is negative, you can work through it.
Kerri Roberts (07:00):
At Permanent Equity, you take a long-term view on everything. How has that shaped how you make decisions and measure success, personally and professionally?
Emily (07:14):
When you’re investing for the long term, you have to choose wisely. There are only so many things you can take on, and you only have so much mental capacity. Everything can look like an opportunity, but we focus on where there’s a strong match.
I think about why we’re the right fit—or not—for an investment. When something doesn’t work out, it’s not a failure; sometimes another partner is simply a better fit. That perspective has been a big lesson.
Another difference is our time horizon. Most private equity firms have a 10-year or shorter structure, which creates pressure to invest, grow, and sell quickly. We have 30 years, which allows us to pace improvements, choose timing carefully, and avoid unnecessary big shifts.
The downside of a long horizon is the temptation to tread water. We focus on continuous improvement, but at a sustainable pace, building energy and momentum over time without forcing massive changes overnight.
Kerri Roberts (11:33):
I’ve seen that. I’ve been in other M&A firms on the insurance side, and the pressure trickles down in ways that are very different from what you’re describing.
Emily (11:49):
Yes. Strategic planning can sometimes look like big, grand plans without enough realistic steps. Then, when things don’t go perfectly, people are frustrated. We prefer incremental milestones and adjusting as we go, because sometimes you don’t even know the best outcome until you’re in the middle of it. That’s why we don’t force massive change quickly.
Kerri Roberts (12:51):
One of your firm’s foundations is “Do No Harm.” What does that mean to you as a leader and in your work with companies?
Emily (13:05):
It comes from the medical principle—don’t start cutting before you understand the patient. In our world, that means taking time to appreciate what’s already working in a business before making changes.
We aim to understand why a company has succeeded and build on that, not impose a one-size-fits-all model. We invite contribution, give people ownership, and allow them to opt in. If someone realizes they don’t align with the direction, they can make that decision for themselves.
When communicated well, people often find new ways to contribute and even get excited about it. But if you communicate poorly, fear and infighting take over, which damages the organization.
Kerri Roberts (15:55):
That makes me think of a client I coach. They’ve been through multiple acquisitions and in this last round, it’s felt like the Hunger Games—people posturing and not protecting one another. It’s heartbreaking because it doesn’t have to be that way.
Emily (16:56):
It sets a tone, and it drains energy that could be spent productively. The “enemy,” if you need one, should always be outside the organization, not within.
Sometimes we discover leaders who’d be happier focusing on a specific passion—like product or customer relationships—instead of managing everything as a CEO. Repositioning people so they can work in their best and highest use benefits the whole organization.
Competition for excellence is healthy; personal competition that breeds trauma is not. We focus on setting clear standards and helping people reach them.
Kerri Roberts (19:47):
Well said, but it can be heartbreaking to watch. You often walk with founders and teams through messy transitions. Other than what we’ve discussed, what do you intentionally put in place to make people feel secure when things are uncertain?
Emily (20:08):
I don’t aim for “safe.” I aim for autonomy and authorship. People should have the ability to contribute meaningfully and to lean into change rather than fear it.
We limit how many strategic initiatives a company tackles in a year to avoid overwhelm. The key is making sure people can see how they fit into the changes and celebrate milestones along the way, which builds momentum.
Kerri Roberts (23:10):
I love that clarity. Clarity is kind—it’s how you take care of people without sugarcoating.
Emily (23:34):
Hiding the truth is what traumatizes people. It’s not fair, and it removes their ability to participate in decisions. People need to know where they stand so they can either engage or opt out.
Kerri Roberts (24:16):
That’s growth—many leaders never get to that mindset. What’s something you’ve personally had to unlearn as you’ve grown in leadership?
Emily (24:22):
Early in my career, I was an individual contributor who preferred doing things myself to ensure quality. That doesn’t scale. It took time and trust to hand work off, accept different styles, and resist taking over.
It’s a common trap for entrepreneurs—just because you’re good at something doesn’t mean it’s the best use of your time. Now, I focus on empowering others to succeed in their own way.
Kerri Roberts (28:03):
Can you share a time when your confidence was tested and how you found your footing again?
Emily (28:13):
A few years ago, I realized I was stuck in high-productivity mode, driven by fear of not being financially secure. I was always working toward a goal I thought was far off, until someone pointed out I’d already reached it.
That shifted my mindset toward contentment and curiosity, giving me more space to be present and to wonder about things outside of work.
Kerri Roberts (31:11):
That reminds me of a speaker I once heard who said if your schedule is so packed you miss helping a little old lady in the grocery store parking lot, you’re missing the point. It took me years to move from an overwhelmed schedule to one with margin.
Emily (31:41):
Exactly. Structure is important, but you need margin—for when you’re not feeling well, for spontaneous curiosity, or simply to think. Appreciating what’s already around you is essential. Otherwise, you’re always chasing the next thing without recognizing current accomplishments.
Kerri Roberts (33:55):
That’s a beautiful and humbling lesson, and I know it resonates with many.
Emily (34:01):
Especially for business owners. They start with a vision and keep pushing toward “the end,” but if you wait until then to appreciate your work, you may be disappointed. Selling the business, for example, isn’t always the ultimate joy people expect—it’s the milestones along the way that matter.
Kerri Roberts (34:56):
What’s something you’re really proud of that’s not on your LinkedIn or resume?
Emily (35:03):
I’m honored when former colleagues or contacts reach out to talk through pivotal career or business decisions—buying a business, making a change, or exploring a new path. It tells me I’ve built relationships where people feel supported, and that’s meaningful to me.
Kerri Roberts (36:29):
This show is called Don’t Waste the Chaos. What’s one piece of chaos in your story that turned out to be a gift?
Emily (36:41):
Becoming a mom. My pregnancy was unplanned, and I was working on a major deal at the time. The pregnancy was difficult, and balancing newborn life with closing that deal was intense.
It humbled me, forced me to adapt, and reshaped my identity as both a mother and professional. Now, I love when my daughter shows interest in my work, and I hope that example benefits her long-term.
Kerri Roberts (40:48):
We have similar stories there. Let’s do a quick lightning round.
Kerri Roberts (41:02):
What’s one daily ritual that keeps you grounded?
Emily (41:02):
Eating lunch alone to recenter, and reading with my daughter at night—non-negotiable for me.
Kerri Roberts (41:36):
A leadership lesson you keep returning to?
Emily (41:40):
Not taking risks can be the riskiest move.
Kerri Roberts (42:24):
A book or podcast that’s shifted how you think?
Emily (42:29):
The Book of Charlie—about a man who lived to 108. It taught me the value of strong relationships and adaptability.
Kerri Roberts (43:08):
Your favorite way to recharge when you’re not “on”?
Emily (43:15):
Running or writing, depending on whether I need clarity or a creative outlet.
Kerri Roberts (43:45):
Emily, thank you so much. We’ll link your organization and LinkedIn in the show notes.
Emily shows us that steady doesn’t mean stagnant, and that building something that lasts requires grit, grace, and a people-first mindset. Navigating big decisions, unlearning old patterns, or leading through change is hard—but worth it.
So don’t waste the chaos. Embrace it. Until next time.
