Future-Proofing Business With AI, Relationships, and Resilience: EO Leaders Share Their Journey

Rise25
25 min read

Michelle BombergerMichelle Bomberger is the Founder and CEO of Equinox Business Law Group, a firm that provides fixed-cost, strategic legal services tailored to the needs of small and midsize businesses. She’s a former Ernst & Young consultant and award-winning entrepreneur recognized for her innovative legal approach.

Michael SacherMichael Sacher is a Partner at WestPoint Financial Group, a firm that offers personalized financial services, including insurance, investment, and retirement planning. With over 20 years of experience in financial services, he mentors advisors and supports his community through organizations like Ronald McDonald House and Habitat for Humanity.

Odette D'AnielloOdette D’Aniello is the Founder and CEO of Celebrity Gourmet Ventures, which includes Celebrity Cake Studio and Dragonfly Cakes — companies known for their custom cakes and artisan petit fours. A third-generation baker, she’s also a podcast host, certified coach, and food finance consultant.

Jonathan Oliff Jonathan Oliff is the Co-founder and Managing Partner of Tim, a South African company focused on AI-driven performance marketing, podcast production, and online education. He brings over 15 years of creative industry experience and co-hosts The Incredible Machines podcast.

Spotify
Apple
Amazon Music
Tune In
Stitcher
iHeart Radio
Deezer

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

  • [1:41] Michelle Bomberger explains Equinox Business Law Group’s proactive, fixed-fee legal model for growing companies
  • [3:01] The challenges of hiring entrepreneurial-minded lawyers and learning to lead over a 20-year journey
  • [5:44] Michael Sacher discusses the impact of economic uncertainty and the importance of authentic client communication in financial advising
  • [8:10] Odette D’Aniello reflects on building a family-run bakery empire from scratch and raising her children alongside her business
  • [11:43] Jonathan Oliff recounts early startup struggles with market positioning and breaking out of the “social media” box
  • [14:43] Why Jonathan compares entrepreneurship to jumping off a cliff and building a plane on the way down

In this episode…

Building a business that can weather uncertainty, embrace innovation, and foster long-term relationships isn’t easy, but it’s what separates thriving companies from those that stall. From legal strategy and financial resilience to brand building and media innovation, how do today’s top entrepreneurs prepare their companies for the future?

According to seasoned entrepreneur Michelle Bomberger, future-proofing starts with aligning services to how clients want to be served, not just how the industry has always operated. She highlights the power of fixed-fee legal models that eliminate barriers to proactive decision-making and explores how coaching legal teams to think like entrepreneurs fosters more valuable client partnerships. This shift not only increases trust but also enables businesses to navigate emerging technologies like AI with clarity. Michael Sacher emphasizes the power of open, authentic communication with clients during financial turbulence, while Odette D’Aniello reflects on building a multi-generational, family-run bakery brand from scratch. Jonathan Oliff adds perspective on storytelling, brand voice, and the scrappy creativity needed to launch a media company in an emerging market.

In this episode of the Rising Entrepreneurs Podcast, recorded live at the Entrepreneur’s Organization Global Leadership Conference in Honolulu, you’ll hear how founders Michelle Bomberger, Michael Sacher, Odette D’Aniello, and Jonathan Oliff are embracing AI thoughtfully, building deep client relationships through transparency, and creating resilience through innovation. You’ll also learn why mindset and strategic coaching are key to long-term success.

Resources mentioned in this episode:

Quotable Moments

  • “Our job is right now is to be there, to be there and to be a resource.”
  • “The roadmap now has become far more confusing than ever.”
  • “You as yourself is vital and important and whatever ideas that give you joy, go for it because it will bloom and blossom.”
  • “You disagree and commit, and then you jump off the cliff and build a plane on the way down.”
  • “Just talk to somebody, get somebody else’s feedback, and somebody… who wants to be there with you.”

Action Steps

  1. Build services around client needs, not industry norms: Adapting your model to meet clients where they are increases trust and long-term loyalty.
  2. Coach your team to think like entrepreneurs: Elevating your staff’s mindset enhances strategic thinking and positions your company for future growth.
  3. Communicate openly during uncertainty: Transparent, authentic conversations with clients strengthen relationships and maintain stability during turbulent market conditions.
  4. Embrace innovation as opportunity, not disruption: Viewing challenges like AI or regulation shifts as growth opportunities helps future-proof your business.
  5. Involve family in your mission when possible: Creating a legacy business with shared values fosters commitment, resilience, and multi-generational impact.

Sponsor for this episode…

At Rise25 we help B2B businesses give to and connect to your ‘Dream 200’ relationships and partnerships.

We help you cultivate amazing relationships in 2 ways.

#1 Podcasting

#2 Strategic Gifting

#1 Our Predictable Podcast ROI Program

At Rise25, we’re committed to helping you connect with your Dream 200 referral partners, clients, and strategic partners through our done-for-you podcast solution.

We’re a professional podcast production agency that makes creating a podcast effortless. Since 2009, our proven system has helped thousands of B2B businesses build strong relationships with referral partners, clients, and audiences without doing the hard work.

What do you need to start a podcast?

When you use our proven system, all you need is an idea and a voice. We handle the strategy, production, and distribution – you just need to show up and talk.

The Rise25 podcasting solution is designed to help you build a profitable podcast. This requires a specific strategy, and we’ve got that down pat. We focus on making sure you have a direct path to ROI, which is the most important component. Plus, our podcast production company takes any heavy lifting of production and distribution off your plate.

We make distribution easy.

We’ll distribute each episode across more than 11 unique channels, including iTunes, Spotify, and Amazon Podcasts. We’ll also create copy for each episode and promote your show across social media.

Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90x, Atari, Einstein Bagels, Mattel, Rx Bars, YPO, EO, Lending Tree, Freshdesk, and many more.

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.

Podcast production has a lot of moving parts and is a big commitment on our end; we only want to work with people who are committed to their business and to cultivating amazing relationships.

Are you considering launching a podcast to acquire partnerships, clients, and referrals? Would you like to work with a podcast agency that wants you to win?

Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

#2 Our Comprehensive Corporate Gifting Program

Elevate business relationships with customers, partners, staff, and prospects through gifting.

At Rise25, thoughtful and consistent gifting is a key component of staying top of mind and helps build lasting business relationships. Our corporate gift program is designed to simplify your process by delivering a full-service corporate gifting program — from sourcing and hand selecting the best gifts to expert packaging, custom branding, reliable shipping, and personalized messaging on your branded stationary.

Our done-for-you corporate gifting service ensures that your referral partners, prospects, and clients receive personalized touchpoints that enhance your business gifting efforts and provide a refined executive gifting experience. Whether you’re looking to impress key stakeholders or boost client loyalty, our comprehensive approach makes it easy and affordable.

Discover how Rise25’s personalized corporate gifting program can help you create lasting impressions. Get started today and experience the difference a strategic gifting approach can make.

Email us through our contact form.

You can learn more and watch a video on how it works here: https://rise25.com/giftprogram/

Contact us now at support@rise25.com or message us here https://rise25.com/contact/

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 from Rise25. I’m here at the Entrepreneur’s Organization Global Leadership Conference 2025, in Honolulu, Hawaii. Beautiful. Honolulu, Hawaii. I’m here with Michelle Bomberger from Seattle.

And Michelle, tell us about your company and what you do.

Michelle Bomberger: 01:41

Sure. Equinox Business Law Group is my company. I’ve had it for 20 years. We’re celebrating this year, and we are a fractional general counsel for growing companies, helping them to be not only reactive to legal and risk management, but also proactive, helping them to think ahead and get to where they want to go in a smart, strategic, safe and secure way.

John Corcoran: 01:59

And from a business perspective, I’m a recovering lawyer, so I know it’s hard to get away from the billable hour. And you have an interesting, innovative model. Talk a little bit about how you were able to figure out how to create that model.

Michelle Bomberger: 02:11

Yeah, I mean, from the beginning, I was looking to overcome those challenges that entrepreneurs and businesses generally have with working with legal. The responsiveness, the fear of cost, the complexity, and how do we meet them where they are operationally, emotionally, financially. And so that was the foundation of fixed fixed fee. And then over time, we found a way to make it all inclusive. So it’s a fixed price over a particular period of time to handle both the proactive and the reactive elements.

So it gives them that experience of having a strategic general counsel on their team, the way a large company does without that concern of should I handle this myself or should I send it over?

John Corcoran: 02:46

Yeah. In 20 years is a long time to have your own company. When you think back to some of the major challenges, maybe, maybe growth stages that you’ve gone through, what are some of those experiences that you’ve had, some of the difficult periods you’ve been through?

Michelle Bomberger: 03:01

Yeah, I would say that growing an innovative model in this industry is really challenging to find the right people and the right lawyers specifically to think about the the business world the way that we need to in order to serve clients the way we do. So the people side is challenging from both the recruiting and finding the right people. And then I think for me personally, the ability to learn to be a leader, to provide clarity, direction, expectations was a long journey, starting with the accelerator program and the People Day and some of those programs that we had through EOA, where I started, and then applying those over my 20 year journey.

John Corcoran: 03:43

Yeah. And you had Covid. That was a big challenge for many companies. What was that experience like for your firm?

Michelle Bomberger: 03:50

Yeah, Covid was an opportunity for us to come together as a team to serve the community. And I was in I had just joined EO. I’d been in EO for a couple of years before that. And within the community, as well as just our broader client base, there were companies that were just collapsing around us, and the emotion around that was, I think, really just hard for all of us to absorb. And I brought the team together and I said, what are what our job is right now is to be there, to be there and to be a resource.

So we did podcasts, we did emails, we did communications with the goal of helping people to feel comfortable. Just like, don’t worry about it, just call. Let’s get through this. And fortunately, our business was okay. We all went home. 

 We had laptops. You know, we were able to to pretty easily adapt. But service was the most important thing that I think we did at that time.

John Corcoran: 04:42

Yeah. And of course now looking towards the future, we’ve got AI which is coming down the pike affecting so many different industries. How do you think about that in terms of affecting your business?

Michelle Bomberger: 04:51

Yeah, it’s a great question. It’s something that is hard, I think, to absorb because there’s so many tools out there. But one of the things that I’m working on with my team is helping them to think more strategically. So we’re doing a coaching program for the lawyers to help them elevate from the day to day tactical into the real work that we do, the real valuable work that we do, which is the thinking. And so teaching them one, how entrepreneurs show up, how does it feel to stand in those shoes?

What are the different parts of the business they need to understand? And then how do they serve as coaches?

John Corcoran: 05:24

Yeah, this has been great. Michelle, where can people go to learn more about you and your firm?

Michelle Bomberger: 05:28

Yeah, I’m very active on LinkedIn. So Michelle Bomberger, there’s only one of me, I think. And then equinoxbusinesslaw.com is our website, and we have a business health assessment there that is a complimentary takes about seven minutes to fill out. And you get a comprehensive report to help you think about risk management.

John Corcoran: 05:42

Excellent. Thanks so much. Thank you. Okay.

Michael Sacher: 05:44

Hi. My name is Michael Sacher. I am a senior partner with WestPoint Financial Group. So what is one major challenge that my company has had to overcome? You know, it’s an odd question because typically when they say when the market is down that people need help or when the market’s up, they have money.

So the roadblocks are really more a function of right now dealing with all the factors that we can’t control. There’s a lot of variables in the financial world. And right now more than ever, they’re coming at us left and right. And we have to try to provide guidance to our clients as to where to go when. The roadmap now has become far more confusing than ever. 

 It’s really all about communication is just being open and authentic with our clients and saying like, look, right now there’s a lot of confusion, there’s a lot of disruption going on in the world today. And I just want you to know I’m here for you. We’re going to talk about it. We’re going to be with you. And it’s really allowed us to connect better and not just rely on the same, oh, the market always goes up. 

 Don’t worry about it. It really is about communication now. So a major milestone that we’re really proud of in our journey has been the fact that year over year, we’ve experienced double digit growth in the overall revenue that our company has produced. And the result of that is because of the advisors that we have and the clients who work with us, continuing to trust us and continuing to invest with us. And that in spite of downturns in the market and economic uncertainty, they’ve continued to stay with us, continue to refer people to us. 

 And the fact that we continue to experience that growth has just been an amazing testament to the advisors in our firm. So as it relates to what are some resources that I think other entrepreneurs should check out? This might sound silly, but I think it’s talk to an advisor. In so many walks of life, we always go see professionals. We go see a doctor when we need help, we go see a mechanic when our car is broken. 

 But unfortunately, in the financial world, we tend to wait until we think everything’s really good before we seek help. And I think just as a simple resource is go talk to a professional, other people in the financial world really know what they’re doing. And just because we all make money and we all think we know how to handle it ourselves. Well, I would encourage you just talk to somebody, get somebody else’s feedback and somebody find somebody who you can trust, who wants to be there with you through the journey. If you’re looking to find me, you can always find me in Cincinnati and at www.westpointfinancialgroup.com or at msacher@financialguide.com.

Odette D’Aniello: 08:10

Hi, my name is Odette D’Aniello and I am the CEO and Founder of Celebrity Gourmet Ventures and Dragonfly Cakes and Celebrity Cake Studio. I also own a garden venue in Tucson, Himalaya Garden. Where did the idea to start my company? Well, I was a teacher and my family. My husband and I moved from Guam to Washington State and we couldn’t find jobs.

And since I grew up in a bakery and I’ve been decorating cakes all my life, we decided to open up a bakery. And that was 26 years ago. Within those 26 years, the hurdles. So many. First of all, a really bad planning. 

 I didn’t have a business plan and basically just kind of leaped into it and fixed it as it went and which was made it really hard. Some of the other challenges is also an opportunity was that I didn’t have children yet and then I got pregnant, raised my kids along with the business. And, you know, I was I basically grew up with this business. And it’s been a journey. And it’s also other challenges would be just working with our, you know, with a team that evolves the there’s a lot of regulations that evolve. 

[Continue to Page 2]

 There’s so many other, you know, there’s other things that you can’t control like Covid. But overall, it all turned out to be opportunities in the in the long run. So I wouldn’t call them challenges. I just call them the opening the doors for opportunity, the major milestones that I’m proud of. Well, I run the business with my family. 

 So my husband and I just celebrated our 29th year anniversary. My sister and I have been in business together for 26 years, and you know, that’s normally not recommended to work with your family, but I absolutely enjoy working with my family. And last year my daughter, who just graduated from the University of Arizona, came into the business and is now the director of marketing, which is a testament to the fact that we have built a business that even my children are proud to continue on in the future. The advice that I would give to other entrepreneurs is to remember that you just being yourself is a gift to the world. Like you don’t have to create anything anymore. 

 You as yourself is vital and important and whatever ideas that give you joy, go for it because it will bloom and blossom. You can find me at on my email at odette@celebritygourmetventures.com I’m actually at celebritygourmet.com. You can find me on LinkedIn and you can also find me on my website. 

 My, I don’t really have a huge social presence that’s open to the public, but LinkedIn would be the best way to find me.

John Corcoran: 11:07

Hey, John Corcoran, I’m here at the Entrepreneur’s Organization Global Leadership Conference in beautiful Honolulu, Hawaii, 2025. And I am a member of EOS San Francisco and also the Co-founder of Rise25 B2B podcast. And I am here with Jonathan Oliff, who’s from Durban in South Africa. And we were just talking about you had one business that you started with, this Conversation Lab started in 2012. I think you said, talk to me a little bit.

We’re asking people about the challenges that they’ve overcome, especially in the early years of starting their business. So what was it like in the early years of starting that company like you got it.

Jonathan Oliff: 11:43

Okay, cool. So thanks. Thanks for having me on. That’s cool. Early, I think early years was getting specific with what we did, and I think they’re still struggling with that at the moment.

But yeah, it was just a it was. And getting the market to understand what we what we were and what and not pegging you into one little pigeonhole. Yeah. So we had a tagline. I came out of TBWA Hunt Lascaris, and I was always going to do my own thing, but I had a couple co-founders and we had this tagline called We Make Brands Social, and everyone just used that and put us in a box of social media. 

 And we weren’t we weren’t that we were. We were a little bit broader than that. We specialized. That was one of our shop ends of the wedge, but it was more about getting brands spoken about, like, is that Oscar Wilde quote? Everyone knows about that. 

 It’s the only thing worse than being spoken about is not being spoken about. So you want you want people saying good things about your brand, but but you want them talking.

John Corcoran: 12:47

So and once people were kind of putting you in the box of social, was it difficult to make, you know, the market, understand that you were much bigger than that?

Jonathan Oliff: 12:57

Yeah. Yeah, exactly. And being like a startup small in an established arena. And South Africa’s very got a high sort of quality product for creativity. So to break through was difficult, but I think we did really well.

We pushed the the press really hard, the press releases, we won some awards early on and then just used that, use the momentum there. And I guess like it’s that that self-belief and entrepreneurial spirit, you disagree and commit and then you jump off the cliff and build a plan on the way down. So it was it was, it was I mean, I’m busy doing it again now. Yeah. And it’s like, I’ve got that. 

 So you know that that there’s some hormone or chemical that’s is produced when in women when they, when they’re pregnant, when they’re giving birth. Have you heard you know that.

John Corcoran: 13:52

So I don’t think so.

Jonathan Oliff: 13:54

It makes them it makes it it makes.

John Corcoran: 13:55

It blocked it out. I have four kids, but they’re a little older now, so.

Jonathan Oliff: 13:59

So there’s a hormone that or chemical I might get that wrong. So excuse me, but that makes the woman the female unit that forgets.

John Corcoran: 14:08

To suppress the pain.

Jonathan Oliff: 14:10

No, just forget or forget. There’s no. Yeah, so forget the pain. Because if they remembered that pain, they would never do it again.

John Corcoran: 14:16

And that’s true. That’s true. My wife has had four kids.

Jonathan Oliff: 14:19

Yeah, so. So. But you were just. I mean, marriages would break up because there would be no more hanky panky or anything like that. So I think maybe entrepreneurs have that same thing because I’m just doing it again, jumping off the cliff and building the plane on the way down and learning as you go.

But it’s amazing.

John Corcoran: 14:33

Well, maybe the the medication that helps with that condition is EO. Right. We’re here at Entrepreneurs’ Organization. What role has that played for you? How has that helped you.

Jonathan Oliff: 14:43

I mean that’s massive. It’s I mean like. It made me realize like my worth. But also I mean, surrounding myself with people better than me and and better me at other things, but like, just better than me and just striving and just learning all the time. So I’ve always been like, a long, a lifelong learner.

But but this is this has been incredibly structured. So whereas I’ll just I’m, I’m kind of interested in a lot of things and this is like way more structured. And that’s been amazing. Yeah.

John Corcoran: 15:17

And what have been your takeaways from this? Beautiful. You must have traveled 20 plus hours to get here. So what have been your takeaways from the last couple of days here in Honolulu.

Jonathan Oliff: 15:26

So 37 hours or 35 here and then 37 on the way back. And and this is the sixth time I’ve done this. Wow. So Hawaii is a special place for me. I used to spend a lot of time on the North Shore and go chase waves there.

And so I went, did that now. And I was actually ran a taxi service when I was there when I was a kid, when I was studying. So I would take people from the North Shore to the airport and drop them off and pick people up. And so I went and did that. Now with some EU members, I rented a car and then went and picked them up and I didn’t charge them.

John Corcoran: 16:02

I was going to say, hopefully you didn’t charge them the prices you charged back then.

Jonathan Oliff: 16:05

Yeah.

John Corcoran: 16:05

Yeah.

Jonathan Oliff: 16:05

No, but so very nostalgic coming back here and then. Yeah. Hawaii. Hawaii. Just like the phenomenal place.

The energy here is very different to anything I’ve ever experienced other than back home.

John Corcoran: 16:18

And what about the people here.

Jonathan Oliff: 16:20

Are the people are just like, yeah, I love that. It’s just yeah, I don’t know. You have to experience it. You have to experience the Hawaiians to, to explain it. But that aloha spirit and that ohana that they talk about is just it’s just it’s more a feeling that can’t be translated like it’s that lost in translation thing.

I feel it’s just incredible people. Yeah.

John Corcoran: 16:44

And you have a new startup called Tim. Tell us about.

Jonathan Oliff: 16:46

It. Yeah. So Tim is a podcasting and performance marketing agency. So podcasting in Africa or in South Africa at least is is pretty new in terms of the marketing, spinning it off, marketing and doing that sort of stuff. There’s some well-established podcasts there.

But Yeah. We produce, we have our own podcast, but then we produce people’s podcasts and that’s the like I say, the shorthand for this is I’m not trying to be Joe Rogan here. I’d love to produce the next Joe Rogan or Stephen Bartlett or whoever it is, but in Africa. And that would be incredible. So I get those type of people on to the show, and then and they get to experience as a sampling exercise on our show. 

 So you get to experience what a podcast is like. And then if you like it, we just happen to do podcasts. So if you’re no strings attached. But yeah.

John Corcoran: 17:39

Yeah. And where can people go to learn more about you and Tim.

Jonathan Oliff: 17:43

Yeah. So Tim.africa is the website. And then Tim.africa on socials and LinkedIn if you look at that. Yeah.

John Corcoran: 17:51

John, thanks so much.

Outro: 17:52

Thanks for listening to the Rising Entrepreneurs Podcast. This episode is powered by Rise25. Please subscribe and check out future episodes.