302 - From Startups to Success: A Journey in Leadership and Empathy with TranscendAP's Jeffrey Weinstein

Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show, and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Jeff Weinstein, welcome to Listening with Leaders. You are the CEO and co-founder of a company called Transcend AP. Which can be found at transcendap.com. Welcome to the show.

Nice to be here with you today, Doug. Thank you for having me.

You're welcome. And looking at your backstory, I see that you've been a tech leader for a long time. I lost count, maybe 8 companies, 9 companies you've been.

A fair number of companies. Yes.

A fair number. So why don't you tell us a little bit about your background and your backstory, and then a little bit about Transcend AP.

Sure, sure. I went to college, Alfred University. I'm a mighty Saxon. I'm sure it's in upstate New York, a little small private school. And I had a degree in chemistry and computer science. And when I graduated college, I was tossed up between becoming a chemist and I was interviewing at a pharmaceutical company right here in, in a nearby town in Eatontown, New Jersey. And, and I was also tossing between working at a software company. At that time, software companies were new and hip and, and I was gonna be offered 3 times the amount of money I was gonna be making at the pharmaceutical company. And I decided not to do that and take my job as a, for $10,000 a year at a start at a small software company in Howell, New Jersey.

There you go.

Yes. And Doug, you'd appreciate the fact that as a chemist, as a chemistry person, I was getting a little tired of how my clothes smelled from all the labs that I was in.

Right.

And so that kind of factored into it too. But, uh, I thought software might have been more the cool thing to be involved in.

So you, were you trained in your undergraduate work, uh, in coding and, and— I did.

I took a fair amount. I took a lot of mathematics and a fair amount of coding.

Okay.

And my first job was actually as a implementation product implementer person for a mini computer-based software product.

You'll, I remember those days. You'll be interested to know that I went to Dartmouth College and when I went to Dartmouth, we learned how to code in Beginner's All-Purpose Symbolic Instruction Code on the first timeshare, time-large computer. That was back in 1969. And I think John Kemeny and John Kurtz, John Kemeny was the president of the college at that time, and I think those guys saw what was coming down the road.

Yeah, yeah.

And it wasn't, what, 20 years later that the revolution began, so.

Yeah, yeah.

Pretty crazy. Yep.

So coming outta school and then probably it was very interesting cuz I was a chemistry guy and a computer science guy. And, and when I was working at the software company, probably about a year into me being on site and working with people, the founder of the company asked me if I wanted to get more into the business side. I think he thought how I was like interacting with people and contextually being able to associate what we were trying to do with the, with our solution and how to solve the problems that people were trying to figure out how to solve. So we went to that direction. Later on, I got my MBA at Monmouth University, put myself through both those schools and, and got an MBA in accounting and finance. And, and then I started going down the path of, of working at startups, which—

And most all this was done on the East Coast?

All this was done on the East Coast. I did, for a number of organizations, I did have people in the West Coast and all of the companies that I've worked with were national or international in their scope. Yes.

I've talked to a lot of tech leaders and obviously many of them are based here in California, either in the Bay Area or down in Los— I live just south of Yosemite National Park, but they're either Silicon Valley or down in Los Angeles. Now we call it Silicon Beach, Santa Monica.

Very good.

No, it's pretty, pretty cool that you were, that there was a tech presence in the greater New York area that you were able to tap into.

Yes. New Jersey specifically.

Okay. And So today, now you are the— what caused you to become the co-founder of Transcend AP?

Yeah, sure. I've been involved in, if you look back at my history, I've been involved in a number of companies that have been fairly successful. Right? Most of those have been mid-sized startups and companies that grew to nice mid-sized companies with a good presence, good reputation. I was in between figuring out where I wanted to go and what my next thing was gonna be.. And I've known the, the original founder or the person with the original idea for a number of years. And I thought this would be a, a cool venture. And I did spend about 6 months or so, 6 or 8 months or so working with the team on an interim basis trying to figure out if this was right. So I spent a lot of time figuring out if this was, if this has the right bones to be successful and also if the market was at a place that it made sense for this, for this company to thrive. So I did spend a lot of time listening and talking people and trying to figure out what, what my, and then also just lastly, did it make sense for me where I was in my life and what I wanted to do with my career? So that, that, those things all had to come together.

Sounds like it did. So Transcend AP, it's about accounts payable management. What does the company do and what makes it unique?

Yeah, I think the, the part about accounts payable is very few organizations in the country now are automated. I think roughly only 9% of the companies in the world, in the, in the country are automated. Most have dabbled with things like rudimentary OCR scanning and things like that. What we've done is we really have focused on a full breadth of things that we think automate easily, automate an organization and something that accounts payable team can gravitate to and be successful at. They're usually the organization that has not been accustomed to being automated. We don't want to take a bunch of technology that you need to really, that is not very user-friendly, that's user-friendly and stick it down people's throats.

Right.

And watch them gag. So we don't want to do that. So we've created a very user-friendly environment. We know how to read and ingest invoices very quickly and very efficiently so they could go through a very systematic workflow and go through an easy approval process so that it's very natural to an organization to adopt. And then I guess the other part is that we recognize that we work inside an ecosystem that involves ERP systems. So we integrate real time with the ERP system. So it's nobody feels like we're— they're doing it. They don't really have to go in every day and figure out how to make this collaborate with other systems in place. So we work inside that. We've done a lot of nice things in that area. I'm pretty excited about what we've accomplished.

How long has the company been in existence?

The solution itself has been on the market since 2018. We, myself and my partner co-founded this. This product was part of a consulting company that we took that product and then made it into our own company. And so that launched in November of 2023, and we really didn't get going until January, February 2024.

So it's brand new, brand new.

And we've doubled the client base in the year. Wow. Doubling the size and feeling pretty good about what we're doing. And also, I do want to say that the accounts payable people that we work with are— they, they don't usually get a lot of props on the work that they do. No one ever calls somebody up and says, hey, thanks for doing your job and—

Right. Taking money out of the bank. Right.

Yeah. So I just wanna say, when I listen to them and I hear their empathy, I hear their challenges. I have a lot of empathy for what they're going through.

Mm-hmm.

And, uh, I really like, uh, working with them and listening to what they're trying to accomplish and really appreciating that we're able to help them.

So it's, it's very gratifying. What, what's the perfect client for Transcend AP?

I think the perfect client is, uh, I don't, I guess I probably don't want to, uh, buttonhole this too much in, but it's probably somebody has, uh, $20,000 $30,000 or so invoices up to maybe a million invoices a year. It's probably like a pretty broad range. We do a lot with midsize companies and larger manufacturing companies. We do a fair amount with universities of shapes and sizes. I think the, I think the one thing that is more about us is when somebody really is trying to really figure out how to practically solve the problem and really wants to go in to do that. We're great at that. We're not an organization that will thrive in political discussions and we're not, I don't think we're built for that. We're built more as a folky, let's get it done kind of company and give it, give us the, give us where you're at and we'll help you figure out the right journey for you. That's, I think that's more about us.

Boots on the ground, making it a little bit like that. Yes. Good for you.

Yes.

So you've been doing this kind of work for a long time. You've had a lot of executive positions over the years. What is it that gets you up in the morning and gets you really excited to go to work?

I do want to say that my, I played a fair amount of baseball and basketball growing up, and I was a pretty good point guard, played a couple years in college and I was a pitcher and a shortstop in baseball. And generally, I really like the idea of team building. I like the idea of coaching. I like the idea of mentoring. I enjoy knowing that people have invested their career capital in what I'm doing with them, and I take that very seriously. Mm-hmm. So I, what really gets me going is, is really helping the team be successful, helping us work together, doing good things for our clients. I just got an email out of the blue from one of our clients today who we haven't talked to in a while. And we were helping them through some, helping work through some issues. And out of the blue, we got this email about, she just wanted to tell us how much she appreciated helping her and helping her team get there. And that made me feel really good. I just like being, when I've, after my, my efforts at Right Answers, which was a longer, a long time company, I really sat back and I really thought that the thing I really like to do is I like to mentor, coach, and try to make a difference. Those are really the things I've attached myself to, both voluntarily and at work.

Yeah. I know you're, I know looking at your LinkedIn profile, you're really involved in community service in, in Nutrisia, which is great. So you're, as, as a CEO, you're seeing one of your principal, one of your principal roles is coaching, mentoring, and bringing along people in the organization to help them be the best they can be.

Yeah.

And that seems to be the secret. You're not alone in that. Just about every successful CEO I've talked about talks about how important it is to work with your people and help them do the very best they can be.

Yeah, I think that's what they signed up for.

Exactly.

I think that's what they signed up. And by the way, if they didn't sign up for that, then we're probably not— we're probably not the right— we're probably not the right fit. Yeah.

Exactly.

Yeah.

So Jeff, what is it, what do you think it's unique about you in all these years you've been doing this work that makes you as successful as you are?

I think there's probably two things that I, probably two or three things that I could pinpoint. One is my father told me a long time ago is to, is to get involved in the things you like and financial rewards and accolades will follow. And don't worry about those. Don't chase those.

Right.

I've actually never, so I've actually never chased those things. And so I've, I've always, always thought about the thing that I want to do is always build good things. And so I actually did a talk at Monmouth University the other day to a bunch of kids, seniors in a financial management class. I told them any venture you're going to, make sure your first thing is to understand what it takes to build a great company and get yourself fo— get your rally around that. And then if you get yourself rallying around that, you'll be in a good place. I think the other part is just myself. I think I'm a, I think I get I get myself into a mode where I like to think about others first and me second. And I think that that's probably just an, just from growing up, that's probably just a thing I inherited from my folks and my father specifically. So I think it's probably just something I saw. He was a lifetime educator and I just saw that in him and just, it just, it just worked with me. And then just the last part is I always like to be prepared. I always think that the, I always think that things are won or lost before they're fought.

That's right.

And, uh, so I like to be prepared and I like to, I get that. Yeah. So I like to be prepared.

Yeah. As a, as a trial lawyer, I made sure I was the most prepared person in the courtroom.

Oh, very nice. Very nice. I didn't know you did that.

And the only reason I tried, I was a civil trial lawyer for 22 years, and the only reason I did as well as I did is cuz I was willing to out-prepare the other side.

Oh, very nice.

You're, In listening to you talking, what I'm hearing is leadership empathy, that you really developed the ability to be a leader with empathy for your people, to really understand where they're coming from, what motivates them, what holds them back, and then helping them work through all of that in a way that creates an atmosphere of collaboration and cooperation and productivity. Does that sound about right?

That is, yeah, that, that is right. And I, I all in that process, I do also feel like I wanna create an environment that's fun and where people don't have to be so worried about what they say. Yeah, I think I, yeah, I think I wanted to—

that's important. More important than most people realize. Google did a study, I don't know if you ever run across the Athena study that Google did from 2014 to 2018. Looking at what separated the top 1/10th percent of all of their teams, the super high performers, from everybody else. And the only factor the psychologist could find is a concept known as psychological safety or emotional safety. And when leaders created emotional safety so that people on the teams were not afraid that they were gonna— there was gossip, or they were going to get judged or criticized for what they said, they could make mistakes they could be themselves, just like you're talking about, those teams excelled beyond any other teams in the vast Google universe. And I think that's what you're talking about here.

Yeah. I want to liberate people.

There you go.

So they feel like they can do what they do. And, but at the same time, I want to create some, some expectations. Of course. Of what good is, what excellent is, and what, what's not good. And Yeah. And so I want, I, I, and, and the other part is I want people, I, I also want people to feel like they, they can take what is true pride in what they work. I don't like a trophy for every per— I don't like a trophy for every participant.

Right, exactly.

But when somebody does something, I wanna call 'em out, call that person out and recognize them even for the littlest thing. Like there was, I remember a time, long time ago, I was, we were at a, I was at a company and we were, I thought culturally we were not where we needed to be. And then I found out by chance that one of our, one of the people in my company on the development side decided to do some kind of micro project on the weekend for 3 hours and came back and showed it to one of my people and one of the, one of my VP of development. And then he brought it to me and I don't, he didn't really appreciate what all that meant. This person was taking out their personally allotted time to saying, you know what, this is important to me. And I'm, I remember making a big deal about it and just being very thankful that somebody like that was doing that kind of thing.

Wow.

Yeah.

Yeah. So you sound like you're a pretty good listener. How did you learn how to listen?

I'm not 100% sure. I do have some interesting things in my background growing up that, that made me that I lived in Argentina for a little while. And when I was very young in my 10, 11, 12 years old, and I, I think I probably just had to figure out how to pay attention in that. It might've been all the coaching I was getting and feeling there was somebody there that was trying to teach me something and learn. I'm not sure. I'm not sure if I felt like my parents were good listeners and they knew what was happening. So I'm not sure how I, I'm not sure how I got it, but I do like to listen. I like to, I like when, when we're talking, we put our cell phones down and don't let that interrupt. I like to be in the moment kind of thing. And I, and I got myself into a, a phrase that I like to always remind myself is when I'm in the moment, um, always trying to put myself on the side of the person I'm talking to and where's that person coming from and what are we all trying to learn from each other and, or have fun with each other and what we're trying to do. So I don't, I'm not really 100% sure. Hmm.

What it is.

Yeah.

I, I, what you're talking about is something I call listening other people into existence. To make sure that they feel deeply heard and validated. And in my work, I work obviously as a mediator and peacemaker in high-conflict situations. One of the reasons why conflict exists is because people don't feel heard.

Hmm.

And so what do they do? They shout at each other because they're not being heard. So they just raise their voice and they get angrier and angrier and more frustrated. But if you can listen to people in a very deep way, and make them feel heard and validated from their frame of reference, all of that goes away. Yeah. And no, it's great. Along the same lines of the stuff you've been talking about.

By the way, my, my wife might disagree with how much I might listen.

So if she, if she, it's one thing to listen at work, it's another thing to listen at home.

If she pops in on this conversation, I'm not sure what she would say.

Yeah. Personal relationships. For me, relationship is relationship. It doesn't matter whether it's personal or professional. The key is learning For me, listening is a skill that can be learned and mastered, and it's counterintuitive and counter-normative to really be a good listener. It goes against everything we think we know about listening. But when you do learn it, then everything changes. And whether you're at home with your kids and your wife, or you're at work, you're listening in a very different way for very different things than listening to words. And that has— that can have transformative effects. In all relationships, which is why I'm so passionate about teaching it because I've worked in places as dark as maximum security prisons training lifers how to stop prison violence to the Congressional Budget Office teaching senior analysts how to de-escalate members of Congress and staff.

Wow.

Pretty interesting broad spectrum.

Yeah. Very cool. Very cool.

Very cool.

Yeah.

It's just staying on listening for a second. I'm just, I'm thinking it's one of the picture I'm getting is that in your organization, you're modeling as the leader, CEO and co-founder, you're leading, you're modeling the behavior, you, that you want people to engage in. Would that be a fair statement?

Yes.

Yeah.

I'm trying. I, yeah, I would like for, I would like for people to, I would like for the team to grow on how well they listen to each other and how well they listen to customers.

Really important. Yeah.

And part of the listening part to it is when somebody, when somebody says something to you, sometimes that's not really what they're asking for.

That's correct.

Yes. And so we gotta, we gotta get to the heart of what's actually without saying, hey, that's not really what you're asking for.

Exactly. Yeah, exactly.

But you have to, so there's a patience that has to come from the conversation.

And the other aspect of that is that you can't engage in early problem solving. You'll hear a customer with something going on and the light bulb will go, oh, I know exactly what the problem is.

This is how to fix it.

And then you jump in and start offering advice way, way too early. Customers and people are not going to be open to solution until they feel like they've been heard.

Yes. Uh, and, and also, I think also sometimes we could be a little bit too flip on when we, um, give an answer, right? Or come up with a solution, cuz you don't know the whole picture yet. Right. So, and so sometimes it's, you're, you're jumping the gun.

That's right.

Right. So, so a little humility, uh, goes a long way.

Absolutely.

In that process. Yeah.

So it sounds like you, I know that you're still involved with Monmouth University where you're an alum and you're working You just mentioned earlier that you were talking to a bunch of seniors. What advice do you give to young people today who are coming outta college, going into the workplace? What advice do you give them about what success looks like and how to position themselves for life success? Not necessarily professional success.

Yeah, actually interesting. 'Cause I was just actually like a keynote speaker at an event there at Mammoth about to a bunch of kids, students who were, who I actually went through this process to talk to 'em about. And the interesting part when I was in that mode, I was is actually trying to think through what are they thinking?

Huh.

And, and one of the things that, one of the things that's a little fuzzy in this world today is that the, the, the generation now that's in high school and college and just coming outta college is the whole, is this whole concept that people could be a TikToker and, and a, a, a celebrity all of a sudden. And that's one makes 'em a lot of money and success and money are the two things that are equivalent, right? They're both, they're both the, they both are equal, right? And, and so I was talking to them mostly about the idea of that success and happiness are not necessarily the same thing, that making money and being happy is not the same thing.

That's right.

And so we had a lot of, so I said, so I said, usually the things that are worthwhile take work and take working at it. And I said the, I said the amount of grit that you have to stay with something and the amount of time that you spend with something usually translates into being an expert being a specialist, being somebody you think you're passionate about. So I talk more about self-awareness and knowing what makes you tick. Ah. And don't pretend that the thing that makes you tick is necessarily, is not, is some, don't be shy. The thing that makes you tick are the things that make you proud and go after the things that make you proud and the things you want to be, the things you want to be known for. And so we, so that was a, a big discussion around, so my discussion with them was around, One, no one was being self-aware. The other was starting stuff, right? If you wanna do something, start it. Mm-hmm. And, uh, the other thing was caring. And I said, the one thing that I, when I'm bring, when I'm working with people, the one thing I cannot teach people is how to care. And so when I'm with somebody and they, they're working with me and I know that they care, that really rings a bell to me. And I will go at great lengths to help anybody who I know that cares.

Wow. So that's very similar to the kind of advice I give when I'm talking to young people. I say, money will not make you happy. What will make you happy is finding something that you're passionate about. And I say, for me, it's serving others. And the more I can serve others and help them live happy and fulfilled lives, then the more happy, my, my life is fulfilled. And it's, doesn't matter how many dollars I have in my bank account. What matters is service to others. And so find something that you can become passionate about.

Could not agree with that more. Could not agree with that more. That's, it's a hard, it's a hard, it's a hard, it's a hard dynamic in today's.

It is. And younger, and they're coming outta school and they're, they got a lot of financial pressure and difficult finding jobs. And then they go into the workplace, which can be crushing. And, and the idea of buying a home, which is really difficult under, for the last 4 or 5 years, very difficult. It's tough. And so you're thinking that you're 23, 24 years old and you're focused on accumulation of wealth or maybe just even surviving. And the idea of being of service to others is a difficult one.

But the other thing that, the other thing that I think that puts a little bit of a cloud on this is that I'm not sure when they're in the family environments that they're in, I'm not sure how much people complain about their jobs, like their jobs, what they see in their what they see in the folks and if they like what they're doing, don't like what they're doing. But, 'cause I think when somebody says, when somebody complains about their boss and doesn't like what they're doing, and they talk a lot about money and their homes and—

Right.

The answer to the problem sometimes is not the actual answer that they think it is.

That's because the problem isn't what they think it is.

Yes, exactly.

Right.

So it's a little challenging there.

Yeah, absolutely. One more question. What's coming? And I'll let you go. What's one thing about yourself, Jeff, that we would never know about? Unless you revealed it to us.

In high school, for my sophomore and junior year in high school, I actually lived on the Navajo Indian Reservation in Arizona, in Kayenta, Arizona.

I've been there many times.

So my family, we moved from New York City.

Wow.

On a whim to go out to Kayenta, Arizona.

And I can't think of, I can't think of an environment that could be more radically different than being out in that little desert wide spot on the road.

Yes. And I was, and I was a good basketball player. And on, and the Navajo Nation is known for its basketball. It was quickly, it was a great way for me to adjust and a great way for me to do stuff. I made a lot of great friends, had a lot of great experience. Still have those friends today. So it was really, uh, it was, it was really cool. And, and probably with that, I'm one of the few people, uh, who, who knows a little bit of Navajo.

There you go. Can speak the language.

I don't know if I can speak the language, but But I was able to say a couple of things.

There you go. That's pretty.

So Doug, how does that sound as one of the more innovative?

That is very, that's one of the more unique. Yeah. One of the more unique specialties of all my 300+ years.

There you go. There you go.

Allianta, Arizona. How many people know where that is?

It's halfway. Allianta, Arizona is Monument Valley.

That's right. It's halfway between Flagstaff and Cortez, Colorado.

That's right.

And I've flown over it in my plane many times. I have driven through there from Flagstaff to Telluride, so I know the area. Very well. Yes, Jeff, it's been a great conversation. Thank you so much for your time today. Really appreciate it.

Great being here. Great talk with you. Learned a lot. Thank you, Doug.

You're welcome. Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnoell.com.

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