Investing in People

Jeremy Holland The Riverside Company

Today’s guest is Jeremy Holland, Managing Partner of Origination at The Riverside Company,  and he understands that building relationships is the key to creating long-term value. Jeremy joins us today to share the secrets he’s learned from the world of deals about why investing your time in people can help you achieve more than you ever thought possible. Jeremy explains that while hardly anybody is willing to invest their time in something that does not present an immediate benefit, the fact remains that the more you help others, the more they will want to help you later. What’s more, relational encounters are far more fulfilling than transactional ones. Jeremy shares some tips for how to build meaningful relationships with your team, stressing the value of private, candid conversations. Regarding external relationships with his firm’s clients, having a ‘how can I help attitude’ has proven to pay back its weight in gold, long term. We also get into the idea of goodwill impairments today – situations where an angry outburst can destroy trust built up over years; we talk about how to avoid having these, and the idea that if you take bad news professionally today, you might be able to turn it into the good news you were hoping for in future.

Key Points From This Episode

  • Jeremy’s belief that investing in meaningful relationships is key to creating long-term value.
  • Private, candid conversations with people as a way of building meaningful relationships.
  • How much a person would appreciate honest feedback about their behavior.
  • Using a ‘how can I help?’ attitude to build meaningful relationships outside of your firm.
  • What it takes to truly invest in a person who can’t immediately help you: A time investment.
  • The delayed, long-term payback that comes from investing in helping others.
  • Examples of goodwill impairments and the work it takes to repair those relationships.
  • How to curb a potential goodwill impairment by taking bad news professionally and scheduling a follow-up.
  • The idea that you’ll often win the same deal later if you take an initial rejection well.
  • Discussing James Carse’s idea that the vitality of a garden does not depend on a harvest.
  • An example of how Jeremy helped an old friend get a job at a top-tier firm.
  • The immediate rewards in terms of fulfillment that come with helping others.


[00:00:01] ANNOUNCER: Welcome to Branch Out, a Connection Builders podcast. Helping middle-market professionals connect, grow, and excel in their careers. Through a series of conversations with leading professionals, we share stories and insights to take your career to the next level. A successful career begins with meaningful connections.

[00:00:22] AD: Hey, everyone. Welcome to Branch Out. I’m your host, Alex Drost. Here we are season one, episode 25. Wow, what an awesome experience it has been producing the first season of Branch Out. I want to give you a quick heads up to all of our listeners that we’re going to be taking the remainder of 2020 off, but we will be back in the beginning of 2021 to kick off the second season of Branch Out. If you haven’t done so already, go back and check out the bonus episodes we shared a few weeks ago that highlight a little bit about what we have in the works for season two, certainly some exciting things.

All right, on to today’s guest, Jeremy Holland, Managing Partner of Originations for The Riverside Company, a global middle market private equity and structured capital provider that has made more than 650 investments. Jeremy and I dive into why he looks at his role as investing not only in businesses but also investing in people and how that’s helped him and countless others achieve far more than they ever thought possible. Hope you all enjoy.

[00:01:23] ANNOUNCER: Connect and grow your network. We are on LinkedIn. Search for Connection Builders.


[00:01:30] AD: Jeremy, welcome to Branch Out. I’m looking forward to our conversation today.

[00:01:34] JH: Thanks for having me.

[00:01:36] AD: Jeremy, you are a managing partner of Originations for Riverside. Knowing that your economic model and your business and your role is all about investing in businesses, you and I the other day, we’re having a conversation, and you said to me that you view your key role as actually investing in people. I would love if you could just start by unpacking that for our listeners because I think it’s such a powerful statement.

[00:02:00] JH: Sure. I think you nailed it. The long-term vision is the more you invest in people and relationships, the more long-term value you’re going to create in your network or your system. So while I understand that there are a lot of people in our world that think that the job is to run around industry conferences and grab every business card they can and end up with 5,000 names in their database, personally I would rather really focus on the people that I naturally connect with and really invest time in them and focus on building deep meaningful relationships that at the end of the day will create a difference in each other’s lives.

[00:02:47] AD: I think that’s such a great place to come from. When you talk about building deep meaningful relationships, what are some of the things that you’ve done your career both to those that you work with but also those external constituents that you deal with in the deal process?

[00:03:03] JH: Sure. Internally, I think what’s really important is candor, provided one-on-one. There are a lot of people who think it’s nice not to address issues. What I think is nice is to address it very clearly but privately so that people have the opportunity to correct what might not be working for them so that they can invest the time in bettering themselves. But you’re not humiliating them by doing so in front of other people. So if you look at some of my former colleagues, they remain very close friends where we had very candid conversations when we were colleagues. They, to their credit, worked on those things they needed to improve and they really appreciate the advice in hindsight and they keep bringing it up over the years that nobody ever told me I needed to correct this behavior.

That kind of thing has served me well. I say friend stab friends in the front and that you tell them directly to their face what the issue is and politely so that they can correct, and you become a sounding board. They trust your advice because you’re candid with them.

[00:04:13] AD: I want to dig into that just a little bit there because I think there’s some really great points. One, I’m a big believer in you give praise publicly. You give criticism privately.

[00:04:22] JH: I love that.

[00:04:23] AD: And you want people to know. When they win and when people excel and people are doing well, you want everyone to know they’re doing well but you don’t need to be giving the harsh criticism in public where everyone is seeing that. That just brings a whole another level of vulnerability and an ability to accept that. What I do think that is so important that you said there is you talk – You said I think friends stab each other in the front. I like that and I think that this idea of giving people candid one-to-one feedback, it’s lost so many times because we don’t want to hurt someone’s feelings or we don’t want to upset them or we don’t want to say something.

But imagine if I had ketchup on my face from lunch, and no one ever said a word to me, and I just kept walking around with ketchup on my face. Everyone else can see that I have ketchup on my face, but I have no clue there’s ketchup on my face. For days now, that ketchup is on my face. Weeks, months, it’s still there. Wouldn’t I want someone to say something to me? Wouldn’t I want someone to say, “Hey, you’ve got ketchup on your face,” right? I know that’s such a an obvious example, but the reality is I think for many of us when we have areas of our profession, our life the way we do things that are causing issues, it is like the ketchup on your face because most other people notice it. Most other people are able to see it. We ourselves tend to be blind to those things. If someone doesn’t say, “Whoa. Hey, you’ve got ketchup on your face,” how is anyone going to know? How are you going to be able to fix that and grow, right?

[00:05:49] JH: Right. In my view, if the person doesn’t take the feedback well, my view is that I care enough about you to let you know that other people are noticing this ketchup on your face, using your example. Whether that be a colleague who had a habit of eye rolling when other people spoke had no idea that he was doing it. Another former colleague had his speech littered with um, uh, you know, whatever, and three or four more filler words, trying to think of a couple other examples. I recently was talking to some colleagues about their camera angles now that we’re in Zoom land where they really hadn’t thought about the fact that the cameras pointed up their nose or that only half their face was on the screen and some of these things. But somebody’s got to tell you. It’s only helpful within the team if you can have private candor.

[00:06:42] AD: No. I think you’re so right and it goes back to it. We all know you have to have that trust in an organization to be able to have that true candor and be able to have those conversations. Listen, they can be hard. One, communication in general is hard, especially when you’re communicating around a topic that can be difficult for sides because the way you might describe it and explain it to someone, the other person may not see, may not be ready to hear and understand what you’re saying to them. But to your point, as a leader, as a friend, as just a good human, your responsibility is to help them and to provide and try to help grow that person, especially in a leadership role.

Let’s shift that to the external world because you want to invest in your people and build strong meaningful relationships internally, and I think that goes without saying that that’s fundamental to success. But you’re also in the deal world and a lot of our listeners and a lot of our audience here on Branch Out are people that do work in the transaction world, deal world, relationship-based business world in one way or another. How do you keep that? How do you build those relationships? How do you build them deep? How do you invest in those people? But also to your point, how do you do that without needing to get 5,000 business cards to put in the CRM?

[00:07:52] JH: Yeah. I like the phrase how can I help. So going into calls, I often think about how can I help this person. So if an investment banker is passed along an interesting opportunity, but ultimately our committee decided not to pursue it, I could make that phone call to deliver that message and that could be a negative experience or that could be a positive experience. What I mean by a negative experience is nobody really wants to hear that we’re not pursuing their client, and so that even done correctly, politely, thoughtfully is still a negative experience.

The slight tweak is if I’m to call and say, “It’s not for us, but I know this off-the-radar-screen new private equity firm or this semi-reclusive family office with deep domain expertise in the sector. Would it be helpful to you if I made a warm introduction because I understand the merits of the investment opportunity is just a bit outside of our wheelhouse?” If you’re adding to their process, even if they already know that name, if you’re attempting to add to the process, attempting to add value, they really appreciate it because so many people in our industry are transactional and busy and effectively takers to be crass about it, and they’re not trying to give. They don’t view it as a two-way street.

But going into conversations internally and externally on how can I help with that mindset completely changes the framework, and that doesn’t even necessarily have to be related to an investment. It could be that they’re trying to build a new line of business. They’re looking for an introduction to some specific kind of service provider. You name it. There could be all sorts of facets of how you can help, but building a reputation of someone who gives and helps puts you in a completely different category from the field.

[00:09:43] AD: I want to take an opportunity to just share a little of my own experience around this and I’ve sat in the other seat, right? I’ve sat in the investment bankruptcy, and a story that that I think really hits to what you’re saying is as bankers we were early on in the ophthalmology craze that went on in 2016. We were doing ophthalmology deals earlier than a lot of other firms, and it was when a lot of private equity was starting to look at that. When we finished up that process, we had countless private equity firms reach out to us, and I think a lot of times someone sitting in a banker role might, “Okay. Well, great. Good to connect with you. I’ll put you in our database and remember you for later.”

We would go out of our way and say, “How can we give you some knowledge? Do you want to pick our brains? Happy to talk about it. Happy to share what we knew?” Obviously, you can’t share client information but you can talk a lot of things, right? You know it. You run through a transaction process. The learning curve is huge, and all of a sudden you realize what matters, what doesn’t. You can start to share that knowledge so that other people who are thinking about investments in the space can get ahead of that. We did that probably 30 times, and it was very time-consuming.

I remember it’s probably about 60 to 90 days after closing that transaction, I would spend a bulk of my time interacting with firms, not with any monetary value for us. But by doing that, we built these relationships. Then fast forward a few months, those firms were calling and bringing us in on deals, whether being on a buy side, advisory standpoint, or helping us on having just pick our brain about transactions they’re doing. We very quickly became market experts in that space and had a domain expertise that many other firms couldn’t compare with.

Now, when we’re talking to clients, look at that extra credibility we’re able to bring. All because we helped with nothing in return, right?

[00:11:31] JH: That’s right.

[00:11:31] AD: And that to your point, it’s fundamentally you’re saying, “Hey, how can I add value to whoever I’m interacting with,” rather than just saying, “Is this going to help me right now in the moment?”

[00:11:41] JH: That’s right. The two thoughts that come to mind is you made yourself the thought leader in that industry and a trusted advisor where so many other intermediaries complete the transaction blast out of tombstone and say, “Hey, look at us. We got this done,” and they’re on to the next one. But there’s just that last mile that could be done if you were to go back to all those people and say, “Would you like a quick teach-in on the dynamics, what we saw in the process, what market conditions are like.” Those firms are looking for ways to pull you in.

We’re seeing it more and more all the time. We have our trusted advisors in different niches. To your point about buy sides, increasingly when we know it’s going to be a competitive process and there’s one individual that we know is very deep in that sector, we quickly want them to align with us to make sure that we put our best foot forward in the process and have the best chance to win. So that’s a great example of investing that time.

[00:12:37] ANNOUNCER: This is Branch Out, a Connection Builders podcast.

[00:12:46] AD: Investing that time. Let’s dive in. Let’s peel that back a little bit. Every one of us gets 24 hours in the day, no matter who you are. I’m a big believer that if you ever say I don’t have time, that’s not the right statement. The right statement is I haven’t prioritized that, and I’m guilty of saying I don’t have time. It’s a bad mental programming that I say to myself. But I know at my core it’s I haven’t prioritized that yet. When you sit back and talk about this investing in people, what it really is is time, right? Maybe in some cases, if you’re in a leadership role, you’re investing in the growth and development by putting them through a program or whatever else it might be. But at the core, your real investment is time, which is also your most valuable asset.

You’re a deal professional. I understand what the deal profession looks like. It never stops. You’re drinking out of a fire hose all the time and you probably don’t know what the bottom of your Outlook inbox looks like. You probably didn’t even know it had a bottom. How do you take all of that and manage that and still invest time in people?

[00:13:40] JH: That’s exactly right. The amount of time you allocate consciously or subconsciously communicates to that person how focused you are on helping them. So if you had an intern that reached out and said, “Hey, I have a quick question,” and you said, “Schedule a five-minute phone call,” just to be extreme, a five-minute phone call a month out, that’s completely different than you scheduling a one-on-one 90-minute call and at the end of that say, “Hey, put another one-on-one on the calendar. Let’s follow up every couple weeks. Make sure that you’re getting your questions answered,” they’re going to walk away from that experience viewing things totally differently.

One of the most important things that I’ve done is helped other people find the next steps in their career. One of the things I’ve seen which is really disappointing is when someone is out of work, their experience is often that the vast majority of their rolodex evaporates. They call people and say, “Hey, here’s what’s going on. I need to look for my next position.” People say, “Wow, sorry to hear that. Good luck,” and they’re quickly off the phone because their brain says, “This person cannot immediately give to me.”

I think if you flip that and you lean into those people that you’re comfortable with, you know them, you would be comfortable recommending them, and you really lean in, and instead of saying, “Wow, that’s terrible. I’ll keep an ear out,” instead say, “Let’s get together. Let’s brainstorm on next steps. Let’s get a long lunch on the calendar for this week. Let’s sit down for a couple hours and think about what the action items are that I can do to help you.” That’s completely different. So taking a deep dive, making bets on those people you connect with can pay back.

I’ve had folks in this industry that I didn’t even know that well, but we connected. They seem to be good at what they do, and you invest the time. Nine months later, they find a job. They drive all the way out here and sit down for a casual lunch, and they report back that they called a hundred people and only three helped. That they’re so moved that you, being one of the three that knew them the least, invested so much time in that initial meeting and then followed up with them, as opposed to making them feel awkward about following up with you. Periodically you shoot them a text, “Hey, just checking in. Anything you need from me.” Those little investments go a long way.

[00:16:08] AD: I love that. If I’m hearing you right, stepping back and saying, “Hey, I have limited time. I can’t make time for this,” the point that I think many people are really missing is recognizing the long-term value creation that’s happening, the long-term. When I say value creation, I’m not just talking the monetary compensation that you’re going to receive but the real long-term value increase and impact that you’re able to have by making those investments today and recognizing that it’s the little steps that you have to do today and continuously to really see the benefits as we get longer-term, right? It’s not something that happens immediately.

[00:16:47] JH: That’s right. I think of it in terms of building your bank account of goodwill, instead of building your monetary bank account today. So the more positivity, the more help, the more value you add to others, it continues to build and build and build. If you think about relationships in terms of an entire lifetime, an entire career, however you phrase it, decades, instead of the next quarter meeting, your next month’s goals, next year’s goals, but you’re saying, “This is a person that I value enough that I’m going to continue to pour time into,” I believe that the monetary stuff will work out in the end. Just by building that trust and that relationship, I think that it’s lost on a lot of people how important trust and reputation is to succeeding in your day job and ultimately the financial rewards that come with that.

[00:17:40] AD: I love the goodwill comment. I think for most, for listeners, that’s an area that we can wrap our brains around shift that into the focus of a human-to-human relationship. You do need to go and find that time to invest, and that’s that goodwill build, but you can also have goodwill impairments, right? Goodwill impairments can happen quickly. So I would love to ask you on that topic. Where have you seen areas that either you yourself recognize you’ve made a mistake in the past or you’ve seen others in their career have actions that are goodwill impairments that are going to hurt some of that relationship bank account that they’re working to build up?

[00:18:16] JH: Yeah, unfortunately I’ve seen several examples. One that comes to mind is a former colleague came in second place. Funny how we’re always second, right? Never fourth or fifth but somehow we’re always second place when we don’t win in the process. The person’s natural reaction was to vent to the investment banker and really inappropriately so expletives the whole thing and kind of what you’d imagine a caricature from a movie would reply to something in a business situation. It will take us years to repair that relationship. Even though that person’s no longer with our firm, those are lasting impacts. That impacts not just that person but that impacts our whole brand. That’s not who we are and that’s not how we conduct themselves, and the fact that that person’s no longer here really doesn’t fix. It’s going to take consistency of behavior through many different settings over a long period of time to rebuild that trust and reputation and goodwill from one goof up, one negative experience.

So it’s often important for professionals if they find themselves getting heated, if they find themselves really upset to just get off that phone call and decompress and circle back up and do a post-mortem with the people later, instead of that initial venting push back so that you’re not eroding all that goodwill that have been built up over the prior 10, 20 years.

[00:19:45] AD: I think that’s such a great point, Jeremy. Again, I can speak about this from my experience. I know how it is in the deal world. You experience similar ups and downs in any profession. But in the deal world especially, you’re living in this roller coaster of emotional ups and downs, and there’s no way around it. Anyone who’s been in the deal business, especially if you are either on the sell side or the buy side and a vast majority of your compensation is tied to the success of a deal, that you don’t have control over what’s happening in. There’s so many different parties, and it can be an emotional rollercoaster, and it can make you an emotional wreck in dealing with that.

All of that said, the anger frustration, those emotions, typically there’s something underlying there, right? It’s the anxiety of, “Oh, my gosh. We’re not going to get this deal done, and I was banking on having that this year from a financial standpoint,” or whatever it might be, right? I think it’s important for us in any profession but especially in the deal world. If you do feel yourself getting heated, if you feel yourself getting overly emotional, angry, frustrated, and so many people get hooked in it, and they go and they fire off an email or fire off a phone call, and they attack the other side, and all you’re doing is you’re making someone else put up their own walls and barriers and getting someone that’s going to say, “Well, this guy’s an asshole. I’m not going to deal with him,” right? Nobody wants to be there and what –

It’s so simple to just step back and say, “Well, I just cool off and I come in there with positive energy.” Your outcome, your impact will be so much greater. I know there’s people that will argue and say, “Well, if you don’t show some aggressive and if you don’t go after them and really show them who the boss is, you’ll never win for your client.” No, let’s go have a conversation, a logical rational call-in conversation, and let’s talk about and bring strong viewpoints that describe clearly and concisely why we’re making the argument the way we are. If they have a viewpoint against that, have that rational conversation. But when you start bringing emotions in, nothing good is going to come out of that

To your point, when we’re talking about investing in people, you have to remember that that investment is constantly ongoing and that goodwill impairment will happen, as you said, very quickly and undo 20 years of relationship building and take another 10 years to undo the damage that was done in a singular event, in a single five-minute event.

[00:22:03] JH: That’s right. I often ask my colleagues vent to me, not to them. Let’s get off that phone call and schedule another one, a postmortem for a week out where we can collect our thoughts and present it more professionally. I can’t tell you how many investment opportunities we have won there. We originally came in second place because Riverside does such a great job of taking the bad news professionally and reassuring the investment banker that if anything goes wrong with the selected party, we’re still here. The phrase hanging around the hoop comes up in our industry a lot. Just by reiterating that at our price level, at our bid, we have great conviction, we’ve done a lot of work, we can move swiftly, we’re still here if you need us and resisting that knee-jerk reaction, very frequently opportunities come back around. Just because you resisted that urge, you end up winning.

[00:23:00] ANNOUNCER: This is Branch Out, bringing you candid conversations with leading middle market professionals.

[00:23:09] AD: And the venting comment – For anyone listening out there, listen. We all get frustrated. I’ve been in that place where I’ve behaved poorly. I’ve behaved in a way that I am not proud of in the past and I’m sure I will do it again in the future. I’m not giving my myself an excuse to do it but I know that I’m human and I’m going to make those mistakes. But I don’t want to and what I have to recognize is when I’m feeling that, I have to go vent. Whether that’s venting to myself, meditating, praying, journaling, something that that helps me, or that’s venting to another person, everyone’s going to be different. Everyone has to find out what works for them.

But if you feel that frustration, go find someone and sit down and say, “Hey, I just need to vent for a minute. I just need to talk this out.” You’d be surprised at how quickly your tension and anger and emotion levels will just come back to a normal place, and then you have that control to go back and have that conversation. I promise you the outcomes will be so much better when you have that.

[00:24:01] JH: Absolutely.

[00:24:02] AD: I want to talk on a quote that you had sent me the other day that I thought was really powerful, and this is by James Carse. He says, “Gardening is not outcome-oriented. A successful harvest is not the end of a gardener’s existence but only a phase of it. As any gardener knows the vitality of a garden does not end with a harvest.” Let’s talk on that for a minute.

[00:24:28] JH: That’s right. I saw that, and it really reminded me of a past conversation you and I had had because I’ve been stuck on this analogy for quite some time that so many people in our industry view the audience as an orchard with ripe apples, and they’re trying to pick that low-hanging fruit. If they can shift that mindset and instead be focused on planting seeds in the sense of building relationships for the next 20, 30 years and maturing those along the lines of this quote about gardening, tending to that garden, tending to that orchard, and instead of picking someone else’s fruit, you’re building your own orchard seem to line up with things that we’ve talked about in the past that I call building my arm.

Back to the point about the 5,000 business cards, I’d rather have 80 people in the industry that are such close personal friends, and we’ve invested so much time in each other’s careers. They have a vested interest in your success. I’d rather have that 80-person army that will run through a wall for me than 5,000 business cards of people I shook their hand once at an ACG event years ago, and I can’t even remember any details about that interaction.

[00:25:37 AD: Today, I’m a believer in the fact that when it comes to networking and building out your relationships, you do have to at some level continuously meet new people and find new. That doesn’t mean trying to get 5,000 business cards but that does mean that you need to have some flow of new relationships, and many of those will be people that you might talk to one time because that’s part of the relationship building process. That’s part of it and that’s okay. But all of that said, shifting to your core, to your center, that really does come down to investing for that long term and finding ways to invest in others so that they ultimately become advocates for you and for your own success.

I have seen that play out in in my own life in so many ways where if you just go out and help enough people, you ultimately build yourself cheerleaders. You build people that stand on the sidelines say, “We want you to win. How can we help you,” because you stood on the sidelines and said, “I want you to win. How can I help you,” when you were interacting with them. You do that enough. That will come back to pay itself, and it’s a hard mentality at times. It certainly can be. The more you embrace that, I think the better life gets in the end. The career success is unbelievable in the back end of that.

[00:26:48] JH: Yeah. Some people might be too immediate reward outcome-oriented, but I actually find it fulfilling, far more fulfilling than doing deals. When you help a friend, a colleague, someone in your alumni network find a job they’ve been out of work for a year. It happened this week. Somebody in my alumni network have been out of work for a year and was scratching their head during can they get back in the industry. Not only is he back but with a top tier firm, and it took some investment of time on my part. I needed to reach out to folks that knew me and knew that I don’t just throw resumes around and that if I was presenting this resume to them with the color commentary that I think this person is a winner, a grinder, XYZ.

Beneath that, that they took it seriously because that might be the only resume I’ve ever sent them in our entire relationship. So they paid attention to it. They just forward it to HR. They said, “Hey, can we squeeze him in for the Friday super session and get him through the process ASAP?” Sure enough, the MD calls back and says, “Wow, even though he didn’t go to a top-tier school, your input really mattered here because it highlighted that this is somebody we should pay attention to. Oh, by the way, don’t tell him yet but he’s going to get an offer on Monday.” The person in my alumni network is so thrilled because he wasn’t sure if there was a path back in after being on the bench for a year.

But that’s so much more rewarding than closing your 45th deal in your tenure at your firm. After a while, that just becomes kind of your day job that almost becomes rote. It sounds terrible to say. But when you’ve closed dozens of deals in your career, it’s more of an exhale. It’s not as much of an elation. Personally, I find it far more rewarding to invest that time in people than I do to try to pick those apples from the investment banking community.

[00:28:40] AD: Your contact from your alumni network, they’re going to be willing to go out of their way and help you in any way they can in the future because you were able to help them. The firm that you referred them to, everyone’s looking for good talent. In the end, people are always looking for good talent. So you just helped them place good talent and you didn’t have a 200,000 recruiting fee attached to it. Just think about all of the positive benefits that come out of something like that. Again, you’ve got to make sure you’re making the right intros to the right people. But I’m a huge believer. If you can help someone plug in and find the right role for them, it goes so far.

Jeremy, this has been awesome. Love talking about investing in people. I really appreciate you sharing some of your thoughts and some of your contribution here on the show and looking forward to continuing our dialogue in the future here.

[00:29:25] JH: Thank you so much for having me. I always enjoy the conversation.


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