Powering Growth Through People, Planning, and Purpose With EO Entrepreneurs

Cindy Free is the Owner and CEO of HR Annie Consulting, a firm specializing in human resources support, training, and compliance for small to midsize businesses. With over two decades of experience in HR leadership, Cindy helps companies build strong people strategies. She is known for her pragmatic approach to aligning culture and compliance.

Wesley Naidoo is the Managing Director at Oasis Group, a global provider of information management services including data storage, digital transformation, and secure destruction. He leads strategic growth initiatives and operational excellence across international markets. Wesley brings a track record of leadership in scaling enterprise solutions and managing complex data governance.

Shirley Wiliani is the Founder and CEO of A La C.A.R.T.E. Solutions, a business process outsourcing firm that provides back-office and customer service support to scaling companies. Her leadership focuses on delivering customized, cost-effective operational solutions. Shirley brings over 20 years of experience in helping companies improve efficiency and growth through outsourcing.

Andy Cheng is the Co-founder of OptiNizers, a company focused on optimizing business operations and technology integration for growth-stage businesses. He leverages automation and strategic consulting to streamline systems and improve scalability. Andy has a background in technology consulting and entrepreneurship, helping clients transform operational bottlenecks into growth opportunities.

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

[1:42] Cindy Free shares how strategic planning helped navigate client loss and the pandemic
[8:49] Wesley Naidoo explains how EO connections fueled global and multi-industry growth
[12:37] Shirley Wiliani talks about how core values reshaped her hiring and team culture
[18:16] Andy Cheng describes how delegation helped him recover from burnout and scale with virtual talent

In this episode…

Growing a company takes more than hustle. It requires clarity of vision, strong leadership, and the ability to adapt through every stage. Whether it’s navigating economic uncertainty, building a team culture from the ground up, or learning to let go through delegation, today’s most effective entrepreneurs are aligning strategy with purpose to drive meaningful, lasting growth.

Cindy Free emphasizes how thoughtful planning helped HR Annie Consulting rebound from setbacks and scale during the pandemic, while Wesley Naidoo explains how leveraging EO’s global network enabled Oasis Group to expand across continents and industries. Shirley Wiliani shares how she transformed her hiring process by leading with core values, creating a culture that attracts the right people. Andy Cheng dives into the mindset shift that helped him overcome burnout: mastering delegation and building a business model centered on remote talent.

In this episode of the Rising Entrepreneurs Podcast, recorded live at the Entrepreneurs’ Organization Global Leadership Conference in Honolulu, you’ll hear how Cindy Free, Wesley Naidoo, Shirley Wiliani, and Andy Cheng are using people-first leadership, strategic planning, and personal growth to power their companies forward. You’ll also learn how community, vulnerability, and connection have shaped their entrepreneurial journeys.

Resources mentioned in this episode:

Quotable Moments

“The learning part of EO just it feels sometimes like you’re getting a master’s degree.”
“I just didn’t know what I was doing, made a lot of mistakes. But every one of those misfires was something that I learned.”
“Being a one-man band at the time was also very difficult until…I pivoted to take strategic partners.”
“Culture and core values. Hiring for character and not skill. Knowing what matters to you as a person.”
“I was overworked, I was burning out, and I realized, okay, why don’t I change myself first?”

Action Steps

Create a long-term strategic plan: A clear roadmap helps guide decision-making and provides stability during business uncertainty.
Lead with core values when hiring: Aligning candidates to your company’s values builds a stronger, more cohesive, and resilient team.
Delegate tasks to the right people: Proper delegation prevents burnout and allows leaders to focus on growth and innovation.
Leverage peer networks like EO: Tapping into trusted entrepreneurial communities opens doors to global opportunities and fresh insights.
Prioritize culture during crisis response: Even in challenging times, maintaining cultural integrity supports employee trust and long-term engagement.

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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 everyone. John Corcoran here at the Entrepreneur’s Organization Global Leadership Conference in beautiful Honolulu, Hawaii, 2025. I’m here with Cindy Free from HR Annie. And Cindy, tell us a little bit about what your company is. You’re also based out of Portland. Tell us what your company is and what your company does.

Cindy Free: 01:42

Sure. Yeah. Like you said, our company is called HR Annie Consulting. We’re based out of Portland, Oregon. We serve clients all over the country. We’re in about 30 plus states, actually. And what we do is we help companies with full cycle HR support on an outsourced basis. So if you think about the employee life cycle, that’s anything from thinking about hiring somebody to when somebody leaves the organization. So we do HR consulting, we do recruitment, we do training, and we do pre-employment due diligence.

John Corcoran: 02:12

Okay. And you started the company 15 years ago. What’s the origin story? How did it get started?

Cindy Free: 02:16

Yeah, actually my mom is Annie. So a lot of people ask, Who’s Annie? That’s my mom. You’re not Annie. I’m not Annie, I’m Cindy, but Annie started HR Annie in 2010. She was 65 years old. Her career was in HR, which I followed in.

John Corcoran: 02:33

Late stage entrepreneur.

Cindy Free: 02:34

Late stage entrepreneur, and she started as a retirement job. So for her, she was going to have a few clients. And I had the opportunity in early 2012 to join her. And so in 2012, I joined Annie. We were a very small organization, just the two of us. In 2013, we executed our first strategic planning session, which was a ten year vision, which is 2024, which or 2023? And we just started plugging away at the strategy. The goal was that I would grow the business and eventually own and operate the business, and she could retire at the pace that she wanted.

John Corcoran: 03:15

Wow, very organized of you to do that. And so we’ve had some big ups and downs in that period of time. Covid obviously was a big one. If you reflect back on some of those big challenges, what were some of the big hurdles you had to overcome?

Cindy Free: 03:28

Yeah. Oh goodness, that’s such a good question because Covid was definitely a potential hurdle for us. I mean, it was a hurdle for everybody. But something that happened before Covid happened in about like from 2014 to 2017, where we were such a small organization. We are very referral based and my background is in hospitality and food and beverage. And so in the Portland area, we’re very referral based at that. When we were small in that industry and we had 2 or 3 really big clients and.

John Corcoran: 04:01

A lot of client concentration issues.

Cindy Free: 04:03

Then it was. And so in 2017, by design, one of our largest clients, we hired an HR director for them as they were growing, which was the purpose. But we weren’t able to replace that large client with another large client. And so we really struggled in 2017. And like a lot of entrepreneurs, can imagine or have experience. You just do all of that self-talk like, oh my gosh, it was going so well. And now what business do I have running a business? And you know, all those mean things that you say to each other. And so, you know, back to the strategic plan. I mean, we’ve always had a strategic plan. And so we just, you know, focused on our strategic plan. We focused on business development because the referrals weren’t coming in. And eventually by the end of 2017, we got a really big contract for a well-known pizza chain, and they hired us to do anti-harassment training. So this was before the pandemic, when everything went virtual. And so we were out just, you know, hitting the road doing these, you know, 80 anti-harassment trainings. But it actually allowed us to kind of pick up the business again and get out of the red for that year and start thinking more positively about the company. So when the pandemic hit.

John Corcoran: 05:19

You’d already been through a big crisis, I guess at that point.

Cindy Free: 05:21

We had. And so I had this framework of looking back and trying to decide, okay, if this pandemic, whatever this is, hurts our business, you know, here’s plan A, here’s plan B, here’s plan C, and what ended up happening in the pandemic, though, was air support became, you know, crisis management for companies because my team was learning all of these new languages of Covid and masks and mandates and layoffs and recalls and, you know, all of the things, not to mention just helping employers get get their employees through this really traumatic Nordic experience. So we actually got busier. You know, so we got busier through the pandemic. My team grew a lot during the pandemic because we needed to hire more people. And but it wasn’t fun. It wasn’t the culture and the engagement and all those neat things that we can do in HR. It was it was responsive and reactive and scary and new and, you know, it was taxing. So yes, it’s been nice to kind of get on the other side of that really urgent part of the pandemic and be able to get back to, you know, culture, engagement and compliance.

John Corcoran: 06:34

Stuff you care more about.

Cindy Free: 06:35

Yeah. Well, it’s more fun.

John Corcoran: 06:36

Yeah.

Cindy Free: 06:37

Yeah.

John Corcoran: 06:37

And then what has being a part of EO done for you being a member of EO? How has that played a role for you as a business owner?

Cindy Free: 06:45

Oh my gosh. I mean, I’m just that classic example of EO membership where my kids, my family, my employees, if I ever tried to leave EO, they would be telling me like, no, you’re not going anywhere because there’s so many, you know, personal professional business advantages to being an EO member personally. You know, it’s about connection. I’ve met so many great people. There’s people from all over the world. I’m so honored to be a leader of an industry group, which means I get to work with other industry leaders from all over the country or all over the world. The learning part of EO just it feels sometimes like you’re getting a master’s degree, the level of speakers, I mean, even being at these GLCs where the levels of speakers and content is just so amazing and then, you know, the business connections in this way that’s not, you know, this sort of frustrating networking. You know, there’s no competition. There’s no pushy salesmanship. There’s it’s all about building the relationships and just wanting to support each other. And the forum experience gives us that gives me, and I know everybody else the opportunity to be vulnerable and to share kind of the good, the bad and the ugly. And, you know, I’m sure like my mom, my kids, my friends, you know, they get probably sick of me talking about work. So it’s great to have forum mates that you can have that level of trust and confidentiality with.

John Corcoran: 08:12

Yeah, Cindy, this has been great. Where can people go to learn more about you and learn about your company, about HR Annie?

Cindy Free: 08:17

Yeah, I mean, I’m on LinkedIn, so Cindy Free. Also, our website is hrannieconsulting.com and you can check us out there.

John Corcoran: 08:27

Great, great. Cindy, thanks so much. Hey, John Corcoran here at the Entrepreneur’s Organization Global Leadership Conference in beautiful Honolulu, Hawaii, 2025. And I’m here with my friend Wesley, who’s from Durban in South Africa. You are the president and also involved in a bunch of different areas. But you have a company called Oasis Group about a ten year old company. How did you end up founding that company? What’s the founding story behind it?

Wesley Naidoo: 08:49

Thanks, John. Yeah, it’s amazing to be here. So I actually was involved in construction back in my country and in the public sector, and I decided to move more into the private sector. And when doing that, I started to look for small companies to acquire or just to get involved in, to get into the private sector. Then I found out that the outdoor advertising industry was quite a good industry to get into, and I spent about two years researching it. That then founded the Oasis Group, where I started to acquire property to set up these outdoor advertising billboards. From doing that, that industry is quite a passive income industry, which gave me time to then look into manufacturing the manufacturing space. And then I started looking into the clothing manufacturing, the oil and gas space. And that led me to invest in smaller companies in those different verticals. And from there, it just spiraled on to building relationships in different industries and within the EO ecosystem. I was able to leverage the networks and the relationships and just grow the company from strength to strength.

John Corcoran: 09:53

So quite diversified in a lot of different areas. What about the early days? What were some of the big challenges when you first got started with the company?

Wesley Naidoo: 10:00

So in South Africa, being a young person was quite difficult and intimidating. A lot of the older people, you know, had these successful companies. So when you go into those type of companies, you’re being this little small guy trying to penetrate their companies. It was a bit difficult. And being a one man band at the time was also very difficult until I realized and I pivoted to take partners in strategic partners who are, you know, involved in those specific industries. And that’s what I found that worked for me. And I’ve stuck with that recipe ever since.

John Corcoran: 10:31

Yeah. And you have been in NIO for about four years now. And president involved in a bunch of different areas. What role has EO played for you as an entrepreneur? How has it helped you and your company personally?

Wesley Naidoo: 10:43

EO has been amazing. I mean, just the community to be a part of this organization, you know, to to meet people like yourself, meet people in different industries globally has allowed me to expand my business globally. You know, from setting up a company in Florida to Dubai, all with your members and just being able to explore the different opportunities with your members. It’s such a trusted network that when you when you communicate or converse with these members in WhatsApp groups or the different portals, you can do so with the ultimate trust and confidence that no one’s going to, you know, try and take you, take you down in terms of a deal you’re trying to do.

John Corcoran: 11:17

Yeah. And tell us about ignite. Ignite is this conference. It’s a regional conference. I believe it rotates from city to city. It’s going to be in Durban.

Wesley Naidoo: 11:25

That’s correct. Ignite is going to be from the 8th to the 10th of July. Sorry, 8th to the 10th of June in Durban, South Africa, at Zimbali Resort. We’ve taken over a whole resort. It’s going to be a next level conference. We already almost sold out. There’s still a few tickets left if people want to join. And yeah, the events. It’s one of the few events in EOH that you can actually come and solicit your your business. You can come, you know, solicit the heck out of it. And the events around the theme is the Power Within. That’s our theme that we’re going with. And we’ve got amazing speakers. The committee that I put in place has done an amazing job, you know, with different experiences, different touch points that the members are going to experience when they come.

John Corcoran: 12:03

Awesome. Wesley, where can people go to learn more about ignite and also your company, Oasis Group?

Wesley Naidoo: 12:08

I’ll share the website link for, ignite. You can find it on the website. And also Oasis Group is oasisgroup.co.za.

John Corcoran: 12:18

Okay great. All right. Thanks so much Wesley. Thank you. Hey John Corcoran here. Coming to you live from Entrepreneurs’ Organization Global leadership Conference in beautiful Honolulu, Hawaii 2025. I’m here with Shirley Wiliani, who’s from Los Angeles and the Los Angeles chapter. And Shirley, tell us a little bit about what your company is and what your company does.

Shirley Wiliani: 12:37

Sure. So my company’s name is a la carte Solutions, and we are a CFO advisory, outsourced accounting and HR consulting company.

John Corcoran: 12:45

And you started that 15 years ago. How did. What’s the origin story? How did you get started?

Shirley Wiliani: 12:49

Yeah, 15 years ago this month actually. So I started my career at KPMG, which is a very well-known known international accounting firm, and I was on the audit side. I got my CPA license and I got out as fast as I could. Went to work for a handful of privately held entrepreneurial type companies as controller VP of finance CFO. Worked my way up. I was miserable the entire time. And in 2010, I was working for a very large commercial construction company, and I was the CFO, and we fell on pretty hard times.

John Corcoran: 13:22

It was a tough time of the era.

Shirley Wiliani: 13:25

Mortgage meltdown. Yeah. And I had to make a tough decision because I had one way, one foot out the door, and I felt it’s not quite right to lay other people off. And so I laid myself off, and I turned that last employer into my first client. And I started billing my time by the hour as a fractional CFO.

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Search Interviews:

Powering Growth Through People, Planning, and Purpose With EO Entrepreneurs

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

In this episode…

Resources mentioned in this episode:

Quotable Moments

Action Steps

Sponsor for this episode…

#1 Our Predictable Podcast ROI Program

#2 Our Comprehensive Corporate Gifting Program

Episode Transcript:

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