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Behind the Scenes With EO Leaders: Overcoming Business Challenges With Community, Strategy, and Grit

Stephanie WaldropStephanie Waldrop is the Principal of Employee Benefits International, a firm that designs data-driven, cost-effective employee benefits for midsize and large employers. With 25-plus years in the insurance industry, she brings deep expertise in strategic planning, compliance, and client-focused service.

Chris SchalleurChris Schalleur is the CEO of Christo IT, a Philadelphia-based company providing managed IT, cybersecurity, and cloud solutions for small and midsize businesses. He founded the firm in 1999 to bring enterprise-level technology support to growing organizations.

Ed HowieEd Howie is the Founder and CEO of BTYcreative and Serve Others Well, branding and customer experience firms that help businesses grow through strategic messaging and client loyalty. He’s worked with brands like Chick-fil-A and 7-Eleven and hosts The Wonder of WOOO podcast.

Sejal Lakhani-BhattSejal Lakhani-Bhatt is the CEO of TechWerxe, an IT services company delivering tailored managed support and cybersecurity for small to midsize businesses. A former banking executive, she’s guided TechWerxe to national recognition among top IT and security providers.

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Here’s a glimpse of what you’ll learn:

  • [1:40] Stephanie Waldrop explains how breaking away from the “healthcare machine” inspired her to launch an independent benefits consulting firm
  • [6:53] Chris Schalleur reflects on losing a key employee and the ongoing challenge of building resilient teams in a fast-changing IT environment
  • [9:52] Ed Howie shares how the “schizophrenia” of shifting entrepreneurial roles impacts long-term identity and leadership
  • [18:08] Sejal Lakhani-Bhatt describes how she transformed from stay-at-home mom to CEO
  • [21:04] Sejal recounts how EO helped her navigate leadership and life after the sudden loss of her husband

In this episode…

Building and scaling a business is never a straight path — it’s filled with unexpected setbacks, major transitions, and the constant need to adapt. But for the entrepreneurs who stay grounded in purpose, embrace community, and remain open to reinvention, those challenges become the catalysts for growth. So how do successful founders push through obstacles while staying true to their values?

Stephanie Waldrop emphasizes the power of reclaiming control after a misaligned partnership and how owning every layer of her business unlocked strategic growth. Chris Schalleur reflects on the hard lessons of team turnover and the long game of developing autonomous leadership. Ed Howie explores the identity shifts that come with building a company over two decades and the importance of releasing clients and employees who don’t align with your mission. Sejal Lakhani-Bhatt shares her deeply personal story of losing her husband and co-founder and how she rebuilt the business and her life with the support of EO and a global network of peers.

In this episode of the Rising Entrepreneurs Podcast, recorded live at the Entrepreneurs’ Organization Global Leadership Conference in Honolulu, you’ll hear how these EO leaders are navigating transitions with grit, building resilient companies, and leaning on a global community for support and inspiration.

Resources mentioned in this episode:

Quotable Moments

  • “I could really leverage a community that had been there, done that, or we’re going through the same things.”
  • “So we live, and we learn, and we’re going to get a little bit better each day.”
  • “It is all human connection, and you’re either leaning into the positive of it, or you’re being distracted and brought down by the negative.”
  • “You don’t want every customer. You can’t take care of every customer, and not every customer is reasonable.”
  • “EO is one of those things where you just sort of live in it, and it lives through you.”

Action Steps

  1. Reassess misaligned partnerships early: Identifying and exiting partnerships that no longer serve your vision safeguards long-term strategic growth.
  2. Build leadership that operates independently: Empowering your team to lead without constant oversight fosters resilience and organizational scalability.
  3. Release clients and employees that don’t align: Letting go of poor fits protects your culture and strengthens your brand’s long-term integrity.
  4. Lean on entrepreneurial communities: Surrounding yourself with peers facing similar challenges accelerates learning and supports sound decision-making.
  5. Define clear roles in family-run businesses: Clarifying responsibilities reduces friction, especially when personal relationships overlap with professional ones.

Sponsor for this episode…

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The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

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Episode Transcript:

Intro: 00:02

Welcome to the Rising Entrepreneurs Podcast, where we feature top founders and entrepreneurs and their journey. Now let’s get started with the show.

John Corcoran: 00:12

Hey everybody, this is John Corcoran with Dr. Jeremy Weisz, and this episode is a little bit different. This is a live interview that we recorded at the Global Leadership Conference from Entrepreneurs’ Organization, where some of the best entrepreneurs from around the globe share ideas and to learn about entrepreneurship. And of course, this episode is brought to you by Rise25, where we help B2B businesses to give to and to connect to their dream 100 relationships and partnerships, helping you to run a podcast so that it generates a referral pipeline and ROI.

Dr. Jeremy Weisz: 00:44

Yeah, I mean, John, after both of us have been podcasting for over a decade, the number one thing in our life is relationships, and we’re always looking at ways to give to our best relationships, and we found no better way to do that over the past decade than to profile the people and companies we admire and shout from the rooftops what they’re working on. And this interview is no different. So if you’ve thought about podcasting, you should go to rise25.com to learn more or email us at support@rise25.com.

John Corcoran: 01:11

Thanks everyone. Enjoy the interview.

Dr. Jeremy Weisz: 01:12

Enjoy.

John Corcoran: 01:27

Hey John Corcoran here at the Global Leadership Conference in Honolulu, Hawaii from Entrepreneurs’ Organization. I’m from Rise25 and EO San Francisco, and I’m here with Stephanie Waldrop. And Stephanie, tell us about what your company is and what your company does.

Stephanie Waldrop: 01:40

Sure. My company is Employee Benefits International. And we’re in Phoenix, Arizona. I’m an EO Arizona member, and we do employee benefits consulting, helping employers across the US, ranging from small employers to just over 6000 employees, create cost effective benefit programs to remain competitive as an employer for their employee population. We help manage that risk year over year compliance, the benefits administration and employee engagement into those programs.

John Corcoran: 02:09

You started the company 11 years ago. You had four partners or three other partners originally, which didn’t last for too long. Tell me a little bit about what the origin story was like behind the company. And you ended up parting ways with some of those partners.

Stephanie Waldrop: 02:22

Yeah. Well, I think at the cusp of the origin story is being part of the healthcare machine, if you will, which I think most people within the US can say is broken in many ways. So I spent just over 11 years on the insurance carrier side and felt like I needed to advocate on behalf of employers with all of the knowledge I had gained about how rates are developed. And those costs are managed internally from a profit perspective, and ultimately felt like I could do more from the consulting side to help the employer and the employees. Then I went to a large national firm and realized that, you know, quite frankly, there were a lot of misaligned interests in the industry and found myself once again feeling like I was part of the machine that wasn’t benefiting the employer and the employee.

So that really led me down wanting to start my own agency or leave the industry. I kind of had those choices: do it my way or don’t do it at all. And so I launched the agency with three business partners who were very large in Ohio but wanted to expand into Arizona. And the reason for that was having kind of plug and play. 

 I was working with larger average client size at that point. And so having some some infrastructure, if you will, felt like the right way to go. But about a year and a half into that, my business partners decided to sell their agency, and it eroded a lot of the value of our entire partnership agreement. And that led me to purchasing their shares in the company and ultimately becoming a sole entrepreneur.

John Corcoran: 03:54

And so what was that transition like when you became a sole entrepreneur and you’re running the company completely on your own? Was it? Was there hard parts of it?

Stephanie Waldrop: 04:02

Sure. It was a it was a somersault, to say the very least. I started the company with the understanding that all of this infrastructure was going to be provided, and I could just do what I was very passionate about, which is consulting with the employer and bringing that value and strategy to solving the problems as this whole relationship unraveled, if you will. I had to then be in the weeds of the company. I needed to now understand, you know, the financials, the PNL, the layers, how to how to scale that business as I was growing clientele.

And those were just not things that I set out to do. When I became an owner of the business, I was going to grow and lead a market. And so, yeah, it was quite the somersault. But at the end of the day, just like most things that can fall under a traumatic category, I wouldn’t take it back. You know, I grew tremendously during that time. 

 And to have the autonomy that I have now as a sole entrepreneur, you know, that’s priceless to me.

John Corcoran: 04:59

Yeah. And what role has EO played for you? You’ve been in it for about five years now. How has it been helpful for you as a sole business owner?

Stephanie Waldrop: 05:07

Yeah, so I mean, EO is the best kept secret. I feel like in every community that it’s in. I stumbled upon EO through other business leaders basically sharing with me. You’ve got to you’ve got to get plugged into EO. I never set out to really be the entrepreneur behind my business, if that makes sense.

And I had no formal training in many of the roles that I had assumed. And so I was kind of just learning trial and error, like a lot of people who are starting and scaling something they’re passionate about from the ground up. And so what EO did was really those experience shares those lessons learned. I could really leverage a community that had been there, done that, or we’re going through the same things, regulatory changes, things that were affecting businesses together. And so it really is everything from a resource, a pool of very rich and vast resource pool to to people who are personally invested in your success. 

 I mean, my forum has been together since I started in EO. They were, of course together before I joined them. But just the stability of that group, the depth of those relationships and there’s, you know, there’s there’s not a thing I could go to through as a person or as a professional, as a business leader, that I wouldn’t have a whole community jump on a phone on a moment’s notice to help me through it if I needed it. So the power of EO is just amazing.

John Corcoran: 06:31

Stephanie, thanks for your time. Where can people go to learn more about you and learn about your company?

Stephanie Waldrop: 06:35

Sure. So I’m certainly on the EO directory, but www.ebint.com is my website and certainly you can contact me through that. And my email and cell phone number in the directory. So happy to connect with members and help with anything that they need.

John Corcoran: 06:52

Great. Thanks so much.

Chris Schalleur: 06:53

Hi, my name is Chris Schalleur. I’m with Christo IT Services. We are a managed service provider. We handle help desk and cybersecurity and cloud for small businesses in the Philadelphia area for over 25 years now. Well, I’m going through it right now.

So a key, a key challenge, a hurdle is people. I’m sure I’m probably preaching to the choir on a lot of the people that are watching this, and we just realized that we lost a key person this morning, put in their notice and they’re going to be leaving us. And so we have to go back up the hill again and go and fight another battle. So we live and we learn and we’re going to get a little bit better each day. I feel like the people move a little bit more fluid than, than has been in the previous years. 

 It is a little bit more of a challenge, but it also adds the soup’s not getting stale. How about that? It adds a little bit more ingredients, and the constant churn is something that we’re just going to have to embrace, because that seems to be the way things are moving forward. A major milestone that Christo IT I’m really proud of this milestone for me, because it was one of the original reasons that I came to EO was I was an IT guy and a guy with a laptop and a prayer, and I and I didn’t really have a great playbook on how to lead people. 

 It was one of the reasons I joined EO was I didn’t have that playbook in my head. And so a really great milestone for us has been over the past year, my leadership team has really started to gel and has started to lead themselves and started to lead their teams under them without a constant prodding from me. So kudos to all of them. And I really felt that that was a growth in our in our organization. And I and I direct a lot of that from EO. 

 A key resource that I really lean in on is the community. The IT community in general has been a stalwart throughout the journey. For me, it’s been absolutely uplifting to see some of these people over 25 years in business. People that have formed businesses with me, they’ve grown their businesses. Some of them have sold their businesses and they’re everyone is always so quick with extending a hand, wanting to help. 

 We had several crises over the past couple of years, as particularly with cybersecurity and the community at large is always just very philanthropic, very willing to give, very willing to help. And that translates both into the IT community and here in EO. Chris Schalleur with Cristo IT, we can be found at www.christoit.com serving the Philadelphia area for over 25 years. And we’re always willing to help. 

 It’s our mission statement and it’s been a pleasure.

Ed Howie: 09:52

My name is Ed Howie and I am an EO member. I’ve been a member of EO for 12 years. I am currently serving as the president of our San Antonio chapter, and will be serving another term starting in July. I’m part of several businesses, including being the founder and CEO of BTY, which stands for Boldest Truest You. We’re a strategy firm and we just launched a new company last year called Serve Others Well, and we’re a training company and our overall mission.

Our overall mission through strategy or training, is to really enable people to do all they can with what they have and to do it well. So the longer I’ve been in EO, the more I’ve realized that EO is way more than the local chapter. Even though I’m obviously a huge fan of local chapter and just arriving here in Hawaii kind of late based on a delayed flight. I had been here at the convention center for ten minutes and ran into three, what I would consider close friends just within the first ten minutes. And to me, that was just an incredible reminder that the content’s great and the learning’s great, but it really is reconnecting with all these like minded individuals who truly understand what it’s like to be an isolated entrepreneur and what it’s like to support each other. 

 So as we talk about major challenges we face in business, you know, I’ve my my company BTY, the strategy firm been in business almost 22 years. And it’s interesting that you would think you overcome a hurdle and then you don’t have to face it again. Well, I believe it’s actually rather cyclical. And so with us being a service based organization, it is that fine line of having too many clients and not having enough clients. You know, you want to be able to provide the brilliant service and Intel like we do with strategy, but then you don’t want to have wasted resources because our warehouse, our inventory is our human capital. 

 And so that doesn’t change. Even though the look, the flavor, the tone of it can change. And I’d say the other hurdle of being in business for 22 years is, as you go from someone who’s an incubator launching a company to running a company to wanting to extend the company past your direct involvement. The schizophrenia it creates as far as your identity and knowing when to lean in, lean out, that kind of stuff. It’s not boring, is it? 

 When I started my company 22 years ago, it was very cool conversation with my wife, and the uptake of it was that I wanted to create an enterprise that could help people do all they can with what they had. Not be worried about what they used to have or what they wish they had. But you’ve got this opportunity, this enterprise. What can you do with it to serve as many people well as possible? And I’m really proud that not only have we done that through B2C, but me and some close friends and business partners have started this new company called Serve Others Well, which is kind of like ESO for the brand experience. 

 We have identified what the best practices of the most beloved brands are, and systemizing the way you care for each other, and having the opportunity to teach that to organizations that aren’t having to pay us for strategy, or they’re paying us for Intel Insights and systems that they can then go implement. The magic framework, the magic methodology. The mindset is the wonder of woo. And that is that everything you do to your customers well, and to your employees and to each other either woos or poos. And we think we should woo more and poo less. 

 So favorite resources as an entrepreneur I would tell you, like put the phone down. I mean, oh my gosh, you know how many stories, how many LinkedIn message. And I’m a marketer. But like you’re getting constantly inundated with, oh, here’s a way to optimize your email list or here’s a way to reduce taxes and all this kind of stuff. And I think we get data overload. 

 And we also causes us to question the decisions we already made because all of a sudden we have this new input. So I would say one of the greatest things I’ve found, not only through EO, but just as a business owner, is be and be incredibly curious, but be incredibly careful. Be curious about trying to find information. But at some point you just got to make a decision and go for it and just try to make the best decision. And whatever you decide, live with it and figure it out. 

 Make it better, make it worse, whatever it is. But don’t second guess yourself because our brain works that way, that I can always think of a better way I could have done it. One thing that’s interesting about being in marketing and branding is that one of the foundational principles, if you truly understand what the customer wants. So being in business for 22 years, I will tell you that. And this may sound counterintuitive, it may actually sound wrong, but it’s right. 

 You don’t want every customer. You can’t take care of every customer, and not every customer is reasonable. Now, I believe in proactively serving our customers, that kind of thing. But at the same point, you can only serve reason to reason. And I have seen greater impact on businesses of gently releasing that customer that’s actually not serving your enterprise well, frankly, gently releasing that team member who’s not serving your enterprise well, because, you know, this is I don’t care whether you’re a B2B, B2C, whatever. 

 It is all human connection, and you’re either leaning into the positive of it or you’re being distracted and brought down by the negative. So if you want some more of this Ed Howie wisdom, we actually did just launch a podcast called The Wonder of WOOO podcast. We’ve got about 40 episodes out there. There’s some YouTube out there yet. We’re going to relaunch that later this year, but it’s on podcast for sure. 

 Really talk about how you can inspire yourself and others to serve others well through all different examples, all different types of experiences. I had 17 years with chick fil A, so had a great experience with brands that actually do that very well. And guess what? There’s a secret formula that can apply to everyone. And then if you want to find me it’s edhowie.com or btycreative.com or serveotherswell.com.

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