The Call to Mastery with Jordan Raynor

Will Weatherford (Fmr. Speaker of the Florida House)

Episode Summary

Rethinking the Church’s approach to politics

Episode Notes

Jordan Raynor sits down with Will Weatherford, former Speaker of the Florida House, to talk about the insane plane crash that changed his life his first day working in politics, why politics is a reflection of culture rather than a driver of it, and how the Church can approach 2020 in a different, less polarizing way.

Links Mentioned:

Episode Transcription

[00:00:05] JR: Hey, everyone. Welcome to the Call to Mastery. I’m Jordan Raynor. This is a podcast for Christians who want to do their most exceptional work for the glory of God and the good of others. Each week, I'm hosting a conversation with somebody who is following Jesus Christ but also following world class mastery, trying to do their most exceptional work in their vocation. We’re talking about each guest’s path to mastery. We’re talking about their daily habits and routines, and how their faith influences their work.


Hey! Since the beginning of this podcast, you guys have been asking me for a guest from the world of politics, and I’m thrilled to bring you one of my top three favorite episodes of the Call to Mastery to date with my friend, Will Weatherford.


Will is the former Speaker of the Florida House of Representatives. At the time, he was the youngest presiding officer of any state legislative body in the United States. An unbelievable accomplishment, which Will will tell you in this conversation by the grace of God alone.


Today, Will along with his two brothers, they’re running Weatherford Capital, a private equity shop here in our shared hometown of Tampa, Florida. I’ve known Will for a long time. I respected him for his mastery of the art of politics. I now have a new respect for him as he masters the art of business.


Will and I sat down recently. We talked about the story I never heard before, this insane plane crash, this near-death experience that changed his life on his first day working in politics. We talked about why politics is a reflection of culture rather than a driver of it. Something I think we get wrong a lot in the church. We talked of how we as Christians can approach the upcoming election here in 2020 with a much different perspective and in a less polarizing way.


This was an absolutely terrific conversation. Make sure you listen all the way to the end. There’s so much gold at the end. Without further ado, here's my friend, Will Weatherford.




[00:02:09] JR: Will Weatherford, my friend, thank you for hanging out with me. I appreciate it.


[00:02:12] WW: I’m honored to be here. Thanks for having me, Jordan.


[00:02:14] JR: I want to start with a story that I don't think I've ever told you before.


[00:02:18] WW: This is always dangerous.


[00:02:19] JR: Yeah, this is always dangerous and it has to do with a prominent Democratic figure, so this should be fun. Back in 2012, I don’t know if you even remember this, I was running this tech startup called Citizinvestor, where we crowdfunding these municipal projects. Somehow, I convinced Gavin Newsom to take a meeting with me. So, Gavin was the Lieutenant Governor of California at the time, obviously now Governor. Man, I don’t know what you do as Lieutenant Governor all day, but we spent like an hour and a half just having tea together.


[00:02:48] WW: Well, now you have your answer. They don’t do a whole lot. That’s basically what they were doing.


[00:02:52] JR: We’re having tea for like 90 minutes in San Francisco, and there are three things I remember with this conversation. Number one, I remember him telling me that the wine shop across the street was started by Gary V. That’s a little fun fact. That was fun. Number two, I remember thinking that Gavin Newsom looks exactly like Christian Bale, that kind of threw me for a loop.


[00:03:11] WW: [inaudible 00:03:11].


[00:03:12] JR: That’s right. The third thing I remember was how he couldn't stop talking about Will Weatherford and how big of a fan he was of Will Weatherford’s. At the time, so this is 2012, are you Speaker then or about to be Speaker?


[00:03:25] WW: I was, yeah. I just became Speaker.


[00:03:27] JR: How’d you get to know Gavin?


[00:03:28] WW: That’s a random one. I don’t think anybody has ever asked me that question. I don't go around proclaiming my relationship with Gavin, given how liberal he is.


[00:03:35] JR: That’s a good idea, yeah.


[00:03:36] WW: But he actually is a great guy. I met Gavin because I got invited to be a participant in something called the Aspen Institute-Rodel Fellows program. What they would do is they take 12 Republicans and 12 Democrats from around the country, people that they thought were in unique positions or positions that may ascend to something else. It was a really incredible experience. You got to know everybody that was in your cohort. We would meet twice a year in Aspen. One year, we went to New Orleans, and you’d be there for a week.


I mean, I got to know Gavin on a very personal level. I’ve seen him a few times in California since then and I actually visit him once since he became governor. Interestingly enough, what it made you appreciate is that while your philosophy may be different than people, they can be smart. They can be thoughtful. They can be well-grounded in their philosophy. It's not like they just made something up. It's like they actually have thought this stuff through too. It really challenged me to I think be a better listener and perhaps maybe open to other perspectives.


It didn't change like the – The whole experience never changed anything about what I believe. In fact, it made it stronger. But it made me appreciate other points of view and other perspectives. Gavin was probably as instrumental in that as anybody.


[00:04:47] JR: Such a rare quality in politics today, which is probably why you're not in politics today.


[00:04:50] WW: Yeah. Correct.


[00:04:52] JR: But let's talk about – You’re somebody who’s mastered multiple vocations in different seasons of life, right? First chapter of your career, you’re mastering the art of politics and public service. And today, you're mastering business in private equity more specifically. Let’s talk about the first chapter of your career though, right?


[00:05:07] WW: Yeah, sure.


[00:05:07] JR: Leading up to this run for the House, what was your story prior to that run that led you to run for office?


[00:05:15] WW: My story on how I even started this first professional chapter of my life in politics is a very unique one. I played football with a guy named Jason Bense in college. I was a senior, and he was a freshman. We played the same position. We were friends. His dad was a guy named Allan Bense, and Allan Bense was going to be the Speaker of the House.


[00:05:31] JR: Allan the legend?


[00:05:32] WW: Yeah. I didn’t know much about him at the time. I was a young kid. But after I graduated, I was working in real estate. On the weekends, I moonlighted as an ESPN announcer and I did the color for our college football team. I would travel with the team.


[00:05:44] JR: I had no idea. This is amazing.


[00:05:46] WW: I’ve had a voice. I mean, not a voice. I’ve had a face for radio for quite some time now.


[00:05:51] JR: Thank God this isn’t a video podcast.


[00:05:52] WW: Exactly. I did this and I was around Allan Bense quite a bit; every weekend, 10, 12 weekends a year. So, I get to be about 24 years old. I’ve been out for two years. I'm still working. He approaches me to come and work for him. And so, I become his legislative aide at 24 years of age.


Probably the most impactful part of that story – You have to pardon my deviation here, but my first day on the job, he and I were on a King Air private plane coming back from a fundraiser. Our plane had an electrical fire in the cockpit. We lost complete control of the plane and we went from 5,000 feet of altitude to about a thousand feet of altitude in a few seconds. I thought for sure it was all over, because we were upside down, spiraling towards the earth at 400 miles an hour and on fire, and the cabin was full of smoke.


We miraculously were turned right side up and we did an emergency landing and we survived. That was my first day on the job in politics.


[00:06:50] JR: That’s the craziest thing I’ve ever heard.


[00:06:52] WW: It’s been quite a roller coaster at the beginning and since then. We obviously survived. I went on to serve Allan for two years as his legislative aide. When I left, I moved back to Tampa, and my plan was to go into business. I got a call from a guy named Marco Rubio shortly after that. Sen. Rubio says to me, he’s now the incoming Speaker of the House, “Hey, Will! Tomorrow, Jeb Bush is appointing Ken Littlefield to the Public Service Commission. Ken Littlefield was the state representative from my hometown of Pasco County.


I said, “That’s great, Marco. Well, why are you telling me this?” He said, “Well, it’s eight weeks from election day. The ballots have been printed. They already have Ken Littlefield's name on them, but we have to find a replacement, and the law says the Republican Party of Florida has to choose who will place him on the ballot.” I was like, “That’s great. Why are you calling me?”


[00:07:38] JR: Why are you calling, Marco?


[00:07:39] WW: He said, “Well, I think you should do it, and I’ll support you if you do.” It was one of those times in my life where I knew the Lord was calling me to do something, because I couldn't have planned it. I couldn’t have strategically set it up. It was like – Literally, it just fell out of the sky, and God said, “I’m going to give you an opportunity here and I’m calling you to do something.”


[00:07:59] JR: Total grace.


[00:08:00] WW: It was his incredible. Eight weeks later, I’m an elected member of the Florida House of Representatives. Two years after that, I’m the incoming Speaker of the House of Representatives and I’m 28 years old. I could not have structured this, and it was only by the grace of God I was given the opportunity.


[00:08:15] JR: Go back to the plane crash. This is – I’ve never heard the story before. I can't believe I haven’t heard this. What impact did that have on you psychologically, spiritually? What – Or did you journal throughout that time? What did your journal say? What was going through your mind?


[00:08:29] WW: It was a transformational moment for me in multiple ways. Number one, it was the second time I had come close and had a brush with death. I was in a very serious car accident when I was in high school and I walked away from it. But another gentleman did not. And so, it was kind of the second time I had been faced with a near-death experience.


It was also a time in my life where I was a Christian and a believer but I wasn't necessarily living that way. I wasn’t lost but I wasn't seeking. That night, God did something in my spirit, and there's no question that the next day I woke up and I was a new person and I was transformed in a way where I made sure from that day forward that my life would mean something and that it would have purpose and that that part of that purpose and the most important part will be bringing glory to Him. It was a huge moment for me. Now, that's the biggest thing that happened from that night.


The second biggest thing was Allan Bense had a daughter.


[00:09:24] JR: I was going to say, “Let’s get to that part of the story.”


[00:09:26] WW: Yeah. Her name was Courtney Bense, at the time. Courtney, her mom called her and said, “Hey! Your dad has this new employee named Will Weatherford, and they almost died in a plane crash last night.” She’s like, “Oh, my goodness,” and kind of freaked out. She said, “Yeah, and I think Will’s a little shaken up. I know you don't really know him. But if you could go take him for coffee and just check on him and make sure he’s okay, that’d be great.”


[00:09:47] JR: Oh, man! Sympathy date. This is great.


[00:09:49] WW: That morning after, Courtney takes me out for a cup of coffee and a bagel. It’s the first time I’d ever had a conversation with her. She's now my wife, and we have four children, all under the age of 12. And so, that evening, that brush with death that God spared us from led to a career path. It led to a family. It led to a changed heart. It was like really the most important day of my life.


[00:10:12] JR: What an incredible picture of God's sovereignty and grace. It's like, “Hey! You couldn't have planned, you could have strived your way to these things. It literally fell out of the sky.”


[00:10:23] WW: It literally fell out of the sky.


[00:10:26] JR: Hey! You mentioned you got elected to the House in eight weeks from Marco picking up the phone and giving you a call. You’re in the House from 2006 to 2014, Speaker from 2012 to 2014. But you were appointed – You were elected by your peers as Speaker elect long before that. I don't think a lot of people appreciate how that process works. Talk about how the Florida House selects its Speaker.


[00:10:48] WW: It’s kind of like the Pope when the white smoke comes up, and all of a sudden you have a new person that's in charge. It's not an overly formal process. I mean, candidly, I thought once I got elected, I understood how the process worked because I had been a legislative aide working in the Speaker's office for two years, so I probably more than most of my colleagues actually understood the role of the job. But I was 26 years old when I got elected, and so why would anybody vote for a 26-year-old to be Speaker of the House?


I think it helped that Marco was the sitting Speaker, because he was in his mid to late 30s. There was kind of this young person who was doing an incredible job. I think that maybe dissuade some of the knock that there would be on me. But effectively, you have to get the support of your colleagues.


And I felt like the way that I could contribute most to the state and to my community was by running for Speaker of the House, not knowing if I could win.


Relatively quickly, within my first year in office, secured the votes I guess would be the right way of saying it to be Speaker. But I didn't actually become Speaker for another four years. There’s this big waiting period.


But the way I tell people is there’s term limits in politics in Florida. I mean, we have a $90 billion budget. If you’re running a Fortune 500 company and you’re going to change the CEO every two years, how much lead time would you want to have for one of the future CEOs?


[00:12:03] JR: Yeah, seriously. Yeah. That’s a great point.


[00:12:05] WW: I actually think while there's some flaws in the system, it prepared me for the job because I was able to get behind the curtain for multiple speakers before me and learn what to do it and in some cases what not to do.


[00:12:16] JR: I love the analogy to electing a pope. I was just watching The Two Popes on Netflix. Have you seen this?


[00:12:23] WW: No, I have not.


[00:12:24] JR: It's a terrific movie with Anthony Hopkins. It’s a nominated for a couple Academy Awards. But I'm watching the scene in which they elect the new pope and while my team was prepping for this episode of the Call to Mastery. I literally thought. I was like, “Oh! This is kind of how we elect Speakers in the state of Florida.”


[00:12:38] WW: Exactly.


[00:12:39] JR: I’m glad you made that connection for me. You serve from 2006 to 2014? You toyed with the idea of running for higher office. There was tons of speculation recently that you’d run for Governor in 2018. Why not run?


[00:12:52] WW: I think I said earlier that I felt really called to run in 2006. I mean, it was like God kind of slapped me upside the head with a two by four and said, “This is –”


[00:12:59] JR: Yeah. It doesn’t get clearer than that, yeah.


[00:13:01] WW: Yeah. “This is the way.” I wouldn't say it was as clear as that, but it was pretty clear that God was saying, “I think you need to come home.” I went into office at 26 years of age, newly married with zero children. I walked out eight years later, having been married for eight years and having four children under the age of six. I don't come from wealth. I didn't have some like nest egg I was able to live off of them while I’m up there doing the people's work.


I really felt like I needed to provide for my family. I also felt like I needed to be there for my family. When you're in politics, particularly at the level of Speaker or another statewide office, you’re gone five days a week. I just couldn't bear the thought of waking up one day and all my kids are graduated high school and I wasn't there.


I just said, “I'm choosing them over this and I'm going to build a business and I'm going to have a family and I’m going to be there for my family. If God calls me back, it'll be as clear as it was the first time. But it’s not going to be an ego-driven, ambition-seeking, office-chasing experience.”


[00:13:57] JR: I have so much respect for that. Let's talk about the business. You eluded to it. What are you and your brothers and your team up to at Weatherford Capital?


[00:14:05] WW: Yes. Weatherford Capital is – It was another example of something I never planned. I'm getting good at this, not planning anything and somehow something coming out of it. My brother, Sam, was living in Africa at the time. Sam ran a large investment family office in Beijing, China for eight years. He then launched a fund in Africa and lived in Ethiopia for two years for the same family and had two young children while he was there. It really felt like he was being called to come back to United States.


My brother Drew, who’s my other partner, was running a consulting company. I was really because seeking to do something new and unique, and I'm coming out of office, so kind of I’m exiting. Sam’s at a crossroads professionally and so is Drew, and the three of us had never one time had a single conversation about doing business together to that day. Never.


We grew up in the same room. I’m one of nine children. I have six brothers, two sisters. Sam and Drew and I grew up in the same room, bunk beds. We’d pull out some mattress and we never talked about it ever. I think it was because our career paths were so different. We never even thought that that was in the realm of possibility.


Also, and God like puts us altogether, and we’re having these calls at 12 o'clock at night from Sam in Africa and Drew and me. We’re like, “What if we just did something?” We didn’t really have a plan for what to do. But it became clear over time, and so we really felt like we could leverage our skill sets, our relationships, and our passions by adding value to other people's dreams.


Effectively, when you're in the investment business, whether it's a private equity or venture, you’re typically investing in other founders. I mean, Jordan, you’re a founder, and so you have that passion in you and I’ve seen it. You had to have people who could believe in that passion and that vision you had and buy into it. We love doing that and we love doing it together and we bring different skill sets. We’re in our fourth year now, and it's just been a dream come true. I love it every day. I love waking up and coming in. We’re adding value to the companies we’re investing in and we’re getting better and we’re building a team. It’s just a lot of fun.


[00:16:03] JR: What are the deals you guys are typically doing? Like stage, check sides, etc.


[00:16:07] WW: Yes. I would say we’re a growth equity firm. We try to invest in companies. They could be a venture business but they’re later stage. So, it’s a company that's kind of right on the verge of profitability. Maybe they're doing 15 or 20 million dollars a year in revenue or more or kind of series C, series D.


We’ll also just do really good growth companies, and so very agnostic from an industry perspective. We own part of the largest marina company in the world, so we know over 95 marinas in 17 different states. A company based in Dallas, Texas, they own a lot of marinas here in Florida.


We own a company called PayIt, which is an online payments platform that serves governments. We own a fiber business that has 2,000 miles of fiber-optic broadband here in the State of Florida.


Our investment thesis is pretty broad. But what's very narrow is the quality and the character of the people involved.


[00:17:00] JR: That's the whole game.


[00:17:01] WW: That’s the whole game.


[00:17:02] JR: It’s the whole game.


[00:17:03] WW: You can over complicate this business. I think a lot of people do. It’s really, really saddling yourself up to and yoking yourself to quality people.


[00:17:12] JR: Bet on people, bet on founders, bet on the team, and bet on market. I was talking to an investor when I was in California with Threshold. I said that with an investor, and he made me think a little bit differently about the team question. He’s like, “Yeah. Bet on teams.” But maybe more importantly, bet on market size, because even the best teams are going to screw up. But if they screw up in a big enough market, it doesn't really matter. Would you agree with that?


[00:17:34] WW: Yeah. 5% of $100 billion market is not bad.


[00:17:37] JR: Right. That’s exactly right.


[00:17:37] WW: 5% of $100 million market, hard to build a business.


[00:17:40] JR: Yeah, smart. I just released a new book, Master of One. In the book, I talk about these three keys to mastering really any vocation, right? Number one is apprenticeships. Number two is purposeful practice of the craft. Number three is discipline over time. I’m really curious which of those three keys you found to be most critical for you in your career, either politics or in business.


[00:18:03] WW: I think it's probably discipline over time. I think it’s – Nothing happens overnight in anything, in politics, in business, in your faith. Nothing happens, and so having that discipline. But it’s like if you want to lose weight, you can’t be disciplined for three days because you’re going to – Maybe you can go carbless for three days and you’ll lose 8 pounds, but you’ll gain 12 back six weeks later. How do you lose weight? Discipline. Discipline in what you eat. Discipline in how you exercise. Discipline in your lifestyle.


I think just like it is in our health and our businesses and our strategies for life and our professional careers, having that discipline over time is critical. It’s something I've learned that just pays off and it’s a snowball effect. It slowly but surely gains momentum and strength, and you just continuously get better.


I think that to me – If you’re anybody who’s listening out there that's trying to think through what's the key, it’s building those habits and establishing that discipline. I don't care if you're 15 or you’re 35 when you start. But at some point, you have to say, “I'm going to build in this discipline in my life and then live it out.”


[00:19:08] JR: Talk us through your disciplines, your habits, a day in the life of Will  Weatherford, from the moment you wake up to the moment you go to bed, what does your day look like?


[00:19:14] WW: Well, because I have four kids, it’s a little crowded and noisy in the beginning.


[00:19:18] JR: You don’t say it.


[00:19:18] WW: Yeah. I try to beat them up. I try to get up an hour before they do so that they don't – I could beat them before they wake up and I can have my quiet time. But sometimes, that works. Sometimes, it doesn't. But I do like to have quiet time in the morning. I like to have a cup of coffee and just have quiet time with the Lord or even quiet time with myself before my day starts.


Then it’s kind off to the races. We get – My wife and I are navigating who’s taking the kids to school and things like that. But I think, for me, every day there's a certain amount of things I want to do. I want to have quiet time. I want to have time with my children. Sometimes, that’s more in the morning than it is in the evening. Sometimes, it's more in the evening. I want to try to exercise. That one’s probably the hardest to squeeze in, because of those three it’s the least of the priority. I also want to make sure I'm serving the people I work with.


I always have a busy schedule. My day gets built out like yours in 30-minute increments, and I'm never just sitting around in the office with nothing to do. There's never enough time. But I've realized that in order for me to be the best managing partner of my company, I have to really be serving the people I'm working with and making sure they have what they need. A lot of it is just walking the ship and just making sure you know what's going on and making sure you have your finger on the poles and that everybody has what they need so that they can thrive and succeed. My day is really filled with making sure people can flourish.


[00:20:37] JR: I love that phrase, walking the ship. I found this to be tremendously productive, oddly enough when I was CEO of Threshold. I would do like a 90-minute block of deep work, right? So, working on, I don't know, a deck for investors or a sales deck or whatever. Then for my “break,” I would take 15, 30 minutes and just walk around the office and see which obstacles people are facing and see if I can knock them down or help knock them down. Is that what you were talking about by walking the ship? Do you really do that?


[00:21:03] WW: Yeah. I literally do and I did it when I was Speaker of the House. I would just be walking the halls, popping in on legislative aides, and they’d be like, “Why are you here? Why is the Speaker of the House walking into my office?” I was literally just saying hello, and it does a couple things. A, it keeps you connected to the people you work with. It also allows you to learn what's going on in their life, because most people, when you see them in the hallways, you’d say, “How are you doing?” Everybody says, “I’m doing great.”


Well, most likely, there’s something in their life that’s not going great. If you don’t know what that is, then that’s a friendship that’s somewhat superficial. I want to have meaningful relationships with the people I work with and I can serve them better if I know what’s going on in their life. Just making sure that I'm building relationship all day long with people I work with, people I partner with, companies we invest in, investors who’ve invested in us, I just feel like I'm in the relationship-building business all day long and I love doing that.


[00:21:03] JR: It’s one of the things that was really counterintuitive to me at first, just walking the ship, walking the halls. But it turns out that like some of the most productive conversations I ever had were during those times. Either one personally connected with people on a personal basis, talking about what they did the night before or what they did over the weekend but also professionally.


A lot of times, I would just walk in one of our rooms with our developers and designers, which they probably hated, and just like look over their shoulder, like what they were working on. We talk about new features and how it would best serve our customers. There's a lot of value in that.


Hey, Will! We got people listening to this episode from all vocations, right? We have entrepreneurs and authors. We have VCs. We have teachers and artists. It’s so interesting. The audience has been asking me to talk to somebody from two worlds in particular, Hollywood and politics.


[00:22:42] WW: Interesting. I can’t help you on the Hollywood part.


[00:22:44] JR: No, you can’t. No, you can’t. We got somebody else who can help there. But, no, I think it’s interesting. I think these can be seen as pretty dark places. I mean, listen. Every industry has its darkness. I think a lot of Christians are just wrestling with the question about how does the church be salt and light in politics. Can you talk about your perspective on that very open-ended question?


[00:23:05] WW: Yeah. I think it's getting harder, because politics is a reflection of the culture. It's a mirror image of us as a people, as a unit, Christians and non-Christians. When people complain about the political system, I always say, “Well, you're focusing on the wrong thing, because by the time people get elected, they’re downstream.”


Culture is way up here, making all these decisions upstream and refining the way that people think and act and live. Then we’re just – People are just voting out their values and electing people that see the world completely differently.


It’s like you can literally I think clean out Congress and say, “We’re going to fire all 435 members of Congress and start over from scratch.” There would be zero improvement. Zero improvement.


[00:23:52] JR: You get the same result.


[00:23:53] WW: Because the culture hasn't changed. Politics is a reflection of the culture. It's like – Let me ask you a question. Why was abortion illegal for generations and then all of a sudden it was legal and still legal? Why was gay marriage illegal for many years and all of a sudden it’s legal? What changed? Did the Constitution change? No, the words haven't changed at all. What changed was the culture, people's views, pieces of values.


[00:24:14] JR: You are teeing up one of my most recent favorite soapboxes. Let me rant for a little bit and have you react to this. I’m so fed up with the typical Christian response to politics, which is if we elect the right people, we can overturn all these laws and change people's hearts, right? If we elect the right people, we’re going to overturn Roe v. Wade, and everything is going to be great, right? It’s just not how change has historically happened, right? Big cultural change always starts with hearts and minds. You brought up abortion. You brought up –


I mean, the LGBT movement – Decades ago Hollywood got super intentional about empathetic characters, gay characters, and it worked, right? I would argue the same thing will happen with the abolitionist movement, right? The inflection point of that movement was a novel. It was Uncle Tom's Cabin, but you started to see hearts and minds change and legislative change follow.


Here’s what’s interesting about you though, what I love about your profile. You’ve been on both sides of this. Changing culture both through legislation and cultural creation. Talk about – I think I know your answer to this, so maybe this is a softball. But like which is more effective? How does change work? How should we as Christians who are concerned with big cultural things in our world respond and drive that change?


[00:25:36] WW: I think it kind of depends on what side – Where you want to be in the discussion. I mean, if you want to be on the front lines of it, politics is where it is. You want to have the cultural debate on the floor of the United States Congress. There’s a place to do that. I've been in those big battles philosophically where everybody says what they believe, nobody agrees, and then we vote, and one side wins, right? I mean, nothing changes. You didn’t change anybody’s mind but you got your two cents in.


I think the cultural side is more interesting. I think it has more lasting impact, and it’s a big reason why I didn’t run for office. I literally felt like I could have as much impact on my community, my country, my state by being a voice for things that I value in the culture as much, as I could running for office and giving speeches. I kind of feel like the cultural side is the one that’s more pressing.


I think we’re at such a divisive stage of our politics and our country right now that there is no winning and losing. It's like trench warfare. It's like you win by gaining two feet, and the other side wins by getting two feet. But nothing's changing.


Until we address as a society some of these really big challenges culturally and figure out how to live with each other, it’s going to be tough.


There's Russell Moore with the Southern Baptist group had a really interesting article in the Wall Street Journal. It's probably been six or eight years, and he talked about how Christians in America were going from the moral majority to the prophetic minority. It’s a really, really important piece, because what he basically said was, “Hey! In America, not only for is it okay to be Christian. It was like expected.” I mean, most of American history was like you went to church because everybody else went to church. It was culturally expected, not just demanded.


Now, we’re at a place where the majority of people in America aren't necessarily living that way or believe that way. Christians and culturally, we are in the minority for the first time in American history, and I think we’re having a hard time dealing with it. Guess what? Throughout most of history like, I don't know, a few thousand years, Christians have always been in the minority, always. We’ve learned.


[00:27:41] JR: Called to be faithful presence as the minority in that – A broader goal.


[00:27:45] WW: Exactly. If you look at where Christianity is growing the fastest, it’s in the markets where it’s the most repressed. I just think we’ve got this back as opposed to having this culture war that we’re saying, “Oh! I don't like the way that my country's changing. I’m going to like fight back.” I think we need to do a little bit of a history lesson as a group and say, “Maybe there's another way to combat this.”


[00:28:04] JR: Have you read Culture Making by Andy Crouch?


[00:28:07] WW: No, but I will now.


[00:28:07] JR: Oh, man! I'll send you a copy. Yes. It’s one my favorite reads of all time. Basically, Andy, who’s just a great thinker, talks about how the church's response historically to things at culture that we don't like has been criticism, has been condemnation, has been retreat. When really the only lasting cultural change happens through creating more culture. The way that you change culture is to create more of it, which are these redemptive themes, right? I love that.


Hey! Go back to your time as a legislator for a minute. Can you recall specific moments in your time as a legislator in which you could point to the work and say, “You know what? Yes, that thing that we did, either a law that was passed or an internal policy that you put in place, that is accomplishing the Lord's will.”?


[00:28:51] WW: Yeah. Well, this may offend some people who are listening. But I’m going to do it anyway.


[00:28:55] JR: These are the best answers.


[00:28:56] WW: Yes. We did a lot of things. We cut taxes and we provided – Really got the State of Florida out of terrible financial shape. We’ve reduced the amount of abortions that take place in America dramatically and in the State of Florida even more so because of restrictions that we’ve put in place and things that have to create regulatory environments around. I’m really proud of some of the ground we made there.


But I would say that the thing that I'm proud of that some Republicans and conservatives probably aren't happy about is every year, there's a lady in my community named Margarita Romo, and Margarita is kind of like the Mother Teresa of East Pasco for the poor and downtrodden and in particular the farmworkers. Those people who came here illegally or their parents came here legally and they’re undocumented. She fights for these kids. Every year, she would come and see me, and she would talk to me about how there’s all these kids. They’re doing well in school. They graduate from public high school. They can’t go to college because they get charged at a state tuition.


If you want to go to the University of Florida and you live in Florida, it costs $7,000 a year. If you’re a undocumented kid, it costs 30. It’s prohibitive. They literally just couldn't go to school. Every year, she’d come see me. Every year, I would give her a hug and I tell her I loved her. When she left, I’d say to myself, “There's no way that’s ever going to happen. I’m not going to be the guy that commits political suicide.”


She comes to see my last year. I’m Speaker of the House. She gives me the same speech. She brings a few kids along with her to tell me their personal stories, and I just felt so convicted. I'm sitting there and I'm like, “This is wrong. These are kids growing up in our public schools. They are working and going to school at the same time. Their parents made a mistake but who should be judged by the sins of their parents? We’re punishing these children.”


I just said, “I’m going to do something about it.” I literally decided that day that I was going to pass a bill that would create in-state tuition for undocumented immigrants in Florida. No state had done it in quite some time. It was tremendously controversial.


[00:30:50] JR: Oh, yeah! I remember that.


[00:30:52] WW: Yeah. When it was all said and done, I was able to pass it but it was not without great angst and some leveraging over my friends in the Senate and holding up their bills and their appropriations till I got it.


But I'm proud of it, because it was something God prompted me to do and the political – If I have been worried about my political future or if I had been worried about what people think, I would've just walked away from it. I’ve done that before. I’ve been prompted by God on things and I didn't fulfill what He called me to do.


But this is one where I did, and I knew it was coming from him and I knew it was something I needed to do. I knew it was right and just. I also knew it would have political consequences and I did anyway. I look to that, because there's just not enough of that in politics today. We’re so focused on doing what we think people expect us to do and staying on the script that we don't venture out. When you have an opportunity to bring something just to a situation that is unjust, we’re called to do that. I was glad I was able to participate in it.


[00:31:53] JR: One question I love to ask on this show is which aspect of God's character do you think you most regularly reveal through your work? I’m going to answer that one for you in this instance.


[00:32:03] WW: Okay, good.


[00:32:04] JR: I mean, with this instance in particular, what a beautiful way to leverage your work in the public sphere to reveal God's heart for the immigrant and the vulnerable, right? Yes, these people came illegally, right? That is wrong. We need to deal with that issue. But these kids did nothing wrong, these kids who grew up with the public system. I mean, talk about the vulnerable children of illegal immigrants and just showing God's heart for the immigrant, which is a theme all throughout Scripture is a really, really beautiful thing.


All right. Let’s move away from politics for a second. Let’s talk Weatherford Capital. By the way, I can have both your brothers on this show. I love Drew. I knew Drew relatively well. We’re at Florida State at the same time. I casually know Sam. But the little I know about Sam I really respect and appreciate him. I know you guys all love the Lord. Your faith drives the way that you approach private equity. How specifically does that play out? How does your faith influence the work that you guys do in private equity?


[00:32:58] WW: For us, it makes it less transactional. Private equity is a very transactional business. You’re buying equity or stock in different companies, and your hope is that whatever you invested in is going to be worth more when it's done. There’s a tendency in this business to focus on things like, “Well, how much debt can be put on this business and should we fire the CEO and bring in a new one? Should we do this and should we do that? Should we change our – Go to market strategy and kind of overthink things?”


We really like to focus on the relationship. It's not that we don't care about those things because, of course, we do. We’re in the private equity business. We have to make money for our investors. We’re called. That's our mandate.


But I think being a believer in this business makes us less transactional and more relational. We genuinely care about the people we invest in. We genuinely care about the people who invest in us, and we genuinely care about the team that we've built. I think because of that, God has helped us to see that relationship drive everything and that if you focus on that, all these other components come into play and end up falling in place.


I really felt like the Lord has blessed us with an ability to discern quality people that we should be affiliated with, and that's both as investors and also with the companies that we invest in and the people who are running them. That's where I spend my time and my focus, and I think that my faith really plays a large role in that.


[00:34:25] JR: I’ve heard you guys say that Weatherford Capital is “committed to the common good." That's not a typical phrase you hear on private equity, right? A lot of times you hear, “No, you’re beholden to your investors.” How does your faith inform this idea? What specifically do you guys mean practically [inaudible 00:34:43]?


[00:34:43] WW: Yeah. It’s a double bottom line. Again, if we lose money, then it doesn’t – You’re not creating any bottom line for anybody. But the idea is that we can make money for our investors and maybe even for ourselves and for our partners and at the same time, we can do good. We pay attention to the companies we’re investing in. What is it that they do? Who are they serving? Are we making a meaningful impact? Who are they employing?


For us, one of the best things you can do for anybody, this is not a faith-driven comment but it’s just a logical one, is give them a job. I mean, commerce lifts people out of poverty, right? If we can participate in helping lift people out of poverty by creating more commerce and by adding value to the economy, that's a good thing. And we shouldn't just be talking about the fact that you put in one dollar and got out three and it was such a great deal. It should be about, “Hey! We put in a dollar. We got back three. But look at the impact we had. Look at the –”


By investing in quality leaders who are leading people appropriately with values, you don't really always understand the ripple effect that that can have in a society. We’re just trying to do our part. We’re not trying to like change the game for everybody. We just feel like we have a role to play, and we feel prompted and called to not just focus on the transactional side of this business but to focus on the people.


[00:36:05] JR: We started this conversation with the controversial Gavin Newsom. Let's start to land this plane with another controversial figure in our current president. You were very critical of Donald Trump during his campaign for president, as was I. Man, I’ll tell you what, Will. I’ve honestly really been struggling with this. I used to wear the Republican badge very proudly. Since 2016, I honestly don't know what to call myself. Where are you on the political spectrum these days?


[00:36:32] WW: I'm confused too. Look. I think the president is capable of doing really good things. I think the president has done some really good things.


[00:36:41] JR: Yeah, I do too.


[00:36:42] WW: Unfortunately, our party though has become so tribal, and we hate the other side so much that even when our people make mistakes, we rush to defend them and to justify their actions and their words and their deeds. I have concern about the Republican Party long-term creating a new identity in itself that is in the image of Donald Trump and not in the image of the values that we have had for a very long time.


I think the president, like everybody, there’s things that I can appreciate about him and things that really frustrate me. I'm less concerned. I think Donald Trump is a creature of our culture, as I said before.


[00:37:20] JR: 100%, yeah.


[00:37:21] WW: Donald Trump is not the reason why.


[00:37:22] JR: He’s a reflection of culture.


[00:37:24] WW: He’s a true reflection. That’s exactly right. That’s exactly right. He's the end result. I think our party is going to go through some challenges, because we’re losing our way. I mean, for an example and not to get overly technocratic, but we’re borrowing $1 trillion a year. The deficit is like way out of control. No one is even talking about trying to rein it in. There’s like been zero discussion since Donald Trump got elected by Republicans about reining in the budget.


My friend, Paul Ryan, tried to have that discussion, and he got slapped down and he's not even Speaker of the House anymore. I mean, there's things like that that will have dramatic impact on our children and our grandchildren that we’re just blatantly ignoring because we'd rather demonize the other side or we’d rather demonize a population that's coming here illegally. That shouldn't be, and we should deal with it. But like is that really the most important issue that’s going on in America right now?


I just think the false outrage that we've created in our party about certain issues that aren’t really as important as others and the ones that are really important we’re kind of like swept under the rug is a real challenge. I'm struggling with that, just like you are. I don't have the answer for it. I can point to the Supreme Court and say, “Wow! There’s been some incredible improvements there. I kind of like everybody he’s picked, and that has real meaning.”


But then I can just see the way that he treats people and talks to people and the ego that's involved. I say to myself, “Man, there's nothing Christlike about that.” So, I really struggle.


[00:38:48] JR: One of our question on this front though that I think is interesting for the church to think through as a whole, right? You mentioned that relative importance of issues. I think the church – Certainly over the last 10, 20 years, have been very much single-issue voters, right?


We’re either – One election, it’s like we’re voting based on Supreme Court justices and abortion and gay marriage, whatever. What encouragement would you have to people of faith, people of the Christian faith about thinking more holistically about these decisions? Or are we right to continue down this track of just vote for judges? What’s your take on that?


[00:39:23] WW: I think you're on a right line of thinking here. It's way more complex. You just can’t be a single-issue voter. I know a lot of people are. I think it's unwise to be. Politics is complex, because humanity is complex.


What I really like people to do is think for themselves. I don't really care where someone lands. I don’t really care, because it's okay for someone to have an issue that's more important to them than it is to me. I think that's perfectly fine. That’s part of the process. It's the herd mentality that we have in our political system today on both sides where it's like there's something is established that this is the way that we view things, and this is the hierarchy of the prioritization of those things, and everybody’s got to get in line.


It's that type of herd mentality where people are literally just not thinking for themselves. They're just falling in line. That’s dangerous. It’s dangerous for Christians. It’s dangerous for our country. It's dangerous for the world. This populist movement is a worldwide phenomenon. It is not an American phenomenon. It’s happening in multiple countries across the world. I just think as believers we need to be thoughtful. We need to be introspective, and we need to actually make up our minds for ourselves and not be told what to believe. I think we’ve just for too long look to others to define what the issues are and tell us what we should think. We’ve got to start thinking for ourselves.


[00:40:43] JR: Yeah. Well said. All right, three real quick questions that I end every conversation with. Number one, which books do you recommend or gift the most to others?


[00:40:53] WW: Besides Master of One?


[00:40:56] JR: Besides the obvious, yeah.


[00:40:57] WW: Okay. All right, great. There’s a few that I love to give out. In fact, if you come to our office, we have probably 30 or 40 different books that we have in these book shelves. When I have meetings with people, a lot of times the last thing I'll do is I’ll hand someone a book.


[00:41:11] JR: Oh! Interesting.


[00:41:12] WW: Based on the conversation. I learned that in Andreessen Horowitz. In fact, when I went to a meeting at Andreessen Horowitz’s office in Silicon Valley, on my way out I was handed three or four books based on the conversation I had that day, which I thought was really touching.


[00:41:24] JR: Books are the best gifts, because there are – I think we have such a romantic attachment to books. I think most people can point to a specific book in their life that like really changed their life. So, I love gifting books, and they’re so darn cheap.


[00:41:38] WW: They’re so cheap. It’s a great gift. It says something about them. It says something about you. It's just – I agree with you. It's the best gift. So, we give them out all the time. A couple books I give out all the time and I enjoy, one is called the Grit, and Grit was a book by Angela Duckworth. The reason I love that book is because it's about our success in life, our ability to pursue and achieve our dreams has zero to do with our intelligence and has everything to do with our ability to persevere and overcome.


[00:42:03] JR: Discipline over time.


[00:42:05] WW: That's exactly right. For those who are listening – Sometimes, I think we can be intimidated by those quants and those geniuses that are out there. I'm not one of them but what I am is when I get knocked on the ground, I get back up and I got a fight in me like you have in you. I think Grit for the first time used data and real science to prove that that ability to overcome adversity is way more important than how well you do on the SAT. I always thought it was profound. I give that one a lot.


I love Start with Why by Simon Sinek, because whether you’re giving a speech, leading a group, regardless of what you’re doing, being able to articulate why you're doing something is so important in leadership. It’s completely undervalued. After I read that book and I watched his speech, I don’t know, 8 or 10 years ago, I fundamentally changed the way that I spoke in front of groups and the way that I communicated. I started thinking through quit telling people what you're going to do and how you’re going to do it. Focus on why you're doing it. People can associate with that. It had a really big impact on me and the way that I live my life and communicated. I love to give that book out.


Then I love The Speed of Trust, because –


[00:43:14] JR: Haven’t heard about that.


[00:43:16] WW: The Speed of Trust, Stephen Covey. The Speed of Trust, that’s a great book. Basically, The Speed of Trust is about you can only move an organization if there's trust built into it, and that in the speed at which you can go is predicated on how much trust there is. It’s like I have two partners. They’re my brothers. I don’t trust anybody in the world, except for my wife, more than these guys, right?


Because of that, we’re able to move very fast, right? I don’t have to go back and look at my agreement with them and say, “Oh! What does that agreement say? What does it say I’m entitled to and they’re entitled to,” because I trust these guys. I trust them with my life. If I didn’t have a signed agreement with them, it wouldn’t even matter. I can move fast with the people I trust.


If you have a team and everybody trust each other, you can do a lot more and you can also do it a lot faster. I think in organizations, building trust within the organization from the top all the way down and throughout the organization is critical for success. So, I love to give that book too, Speed of Trust.


[00:44:08] JR: That's a really good. What one person would you most like to hear talk about how their faith influences their work?


[00:44:08] WW: That’s a really good one. Have you done Tony Dungy yet?


[00:44:18] JR: We have an invite out to Tony, and I interviewed him for Master of One. I’m pretty sure he’s coming on the podcast. We don’t have him scheduled yet but –


[00:44:24] WW: I'd like to hear him. I mean, I value him so much. He's a person who’s also had success in different arenas. I like people who have achieved great things but never lost their humility. Tony’s a person who just is never changed, what he cares about, who he is, what he values. No matter what kind of success he has, he is the same person. And I just think that his witness to others is so powerful. I’d love to hear you interview him.


[00:44:50] JR: That's a great answer. Tony and I share an agent, this guy named DJ Snell, who we had on the podcast a while back. I think DJ said this on the podcast. He’s like, “You know, I travel with Tony all over the place for media tours, whatever. I know he is a sinner because the Bible tells me so. But I've never actually seen it.” [inaudible 00:45:08] talking about just how unbelievably humble Tony is. I love Tony.


All right, let’s wrap up with this. Once piece of advice. You talked about a lot of great takeaways but one piece of advice you would give to somebody in this audience who is just trying to do the most masterful work they can for the glory of God and the good of others. What would you tell them?


[00:45:26] WW: Live with curiosity.


[00:45:28] JR: That's good.


[00:45:29] WW: You can't learn if you're not curious. Remember in school and you like hated a class or you just didn't like a subject matter and you were just trying to memorize the topic. But after the test, whether you fail it or you got an A, if I’d ask you two weeks later what was on the test, you couldn’t even remember because you didn’t like it. You weren’t interested, right?


But when you’re interested in something, when you're curious about something, your ability to retain that information and actually synthesize it and do something with it is like 10X.


[00:45:57] JR: Well, Angela Duckworth talks about this in Grit, this – I think she’s called it insatiable curiosity.


[00:46:02] WW: She does, yeah.


I try to tell people, whenever I'm with someone who's at a crossroad, it’s like, “Maybe they don’t like the career they’re in. Maybe they feel unfulfilled.” I try to really ask them, “Do you think you're curious enough? When you see something you don't understand, do you ask why or you just move past it? When you read a book and it doesn't make sense at first, do you research it? Or do you just kind of say, ‘I'll get to that later.’?”


Living a life of curiosity, which requires humility, it requires you saying, “I don't know much of anything but I'm willing to learn. In fact, I'm interested in learning about things that I don't know and I don't understand.” That intellectual curiosity will lead people to amazing places. It’s led me to two totally different careers, and every day I am learning something new. It’s because I'm curious and I hope I can always maintain to have that. I think others should have it too.


[00:46:52] JR: That's terrific advice. Will, I just want to commend you for the excellent, holy eternally significant work that you are doing today and you have done.


Thank you for serving me and my family and the people of Florida well during your time in the house. I always respected your leadership in Florida. Thank you for working to create for the kingdom through Weatherford Capital.


On personal note, thank you for your friendship and always supporting my work. I’m such a big fan of yours.


Hey! If you want to follow Will on Twitter, you can do so @willweatherford. He’s pretty easy to find. He's pretty googleable. Also, you can learn more about Weatherford Capital at Will, thanks for hanging out with me.


[00:47:30] WW: Thank you, Jordan. It’s a real pleasure.




[00:47:33] JR: I love making this podcast for you guys. It's episodes like this that really keep me fired. Hey! If you’re loving the podcast, do me a favor and tell me exactly why. You can do that by leaving a review of the show right now on Apple Podcasts or wherever you review podcasts. Tell me what you like, what you don't like, what we can improve. How can we make this show better for you? I really hope you guys enjoyed that conversation with Will. Thank you for listening to this week's episode of the Call to Mastery. I’ll see you next time.