The Rollercoaster Podcast with Nikunj Kothari

Wes Donohoe - VP of Product at One Medical

October 19, 2020 Nikunj Kothari Season 1 Episode 1
The Rollercoaster Podcast with Nikunj Kothari
Wes Donohoe - VP of Product at One Medical
Show Notes Transcript

For today's episode, we chat with Wes Donohoe (@wesperience). Wes recently transitioned to working on special projects at One Medical after serving as their Vice President of Product for four years. Prior to this, he was the head of product at Shyp and previously head of product at Live Nation Labs. 

In this episode, Wes talks about all his incredible ventures:

  • Being scuba certified for free at age 12
  • Starting his boat cleaning company in college
  • Launching and failing to build three companies after the 2008 financial crisis
  • Transitioning to product management with no prior experience at Live Nation Labs and then joining Shyp
  • Building and scaling the One Medical product org 
  • Steering One Medical through IPO and COVID early this year

Thanks for listening — if you like what you hear, please review us on your favorite podcast platform. 

Check us out on the web at http://rollercoaster.life/ or get in touch with us on Twitter @rollerpod or emailing me at [email protected]

Music: Nowhere land & Wholesome by Kevin MacLeod.
License: http://creativecommons.org/licenses/by/4.0/

[00:01:09]
Nikunj Kothari: Hey Wes, welcome to the show today. I'm looking forward to our chat 

[00:01:13]
Wes Donohoe: Hey, me too. Hi, Nikunj

[00:01:15]
Nikunj Kothari: How are you and your family doing at this moment?

[00:01:18]
Wes Donohoe: Family is healthy and happy. We live here in the city and, my oldest son is in first grade and he's actually starting to go into in-person schooling now. So it's pretty exciting. He's overjoyed. And having a less kid in the house has here fantastic for my and 

[00:01:33]
Nikunj Kothari: It's really great to hear that you and your family are keeping safe. Are you planning to join this mass SF exodus?

[00:01:42]
Wes Donohoe: No, not yet. we love the city and  we think that, yeah, we're just having a great time here in city. So we'll be planning to stay 

I think the contrarian view is that now is the right time to get into SF. So I'm glad that you're staying, but let's get into it. I want to hear all about your incredible ventures. Let's first start with hearing about how you got scuba certified for free at the age of 12. 

So when I in the seventh military boarding st. Petersburg, Florida. And you would think I'd would be a bad kid, but I actually begged my parents to send me there. because I heard that I could to to fly a plane, scuba dive and shoot guns.

And as a 12 year old boy, that seemed like the coolest thing in the world to do. And you could do it in Florida versus Wilmington Delaware where I was from, and so I, when I was, is there, I learned to scuba dive. I got my first school of having license there. And I found out that the kind of local dive shop that I could work out a relationship with them.

Or that I could promote scuba diving on the campus, on my boarding school's campus. And, in return I could fill the classroom and then in return I could work out and get free licenses. And so as a 12 year old, I was shopping to my teachers and staff and for other friends to get a scuba diving license and telling you how amazing was, and ended up getting just an enormous amount of different licenses and anywhere from underwater hunting to advance to rescue to Nitrox. I can breathe different air and stay  longer. So as a, it was a pretty wild ride in a good time. 

[00:03:25]
Nikunj Kothari: When you went to college at Babson. Your next venture was starting your own boat, cleaning company. How did that happen ?

[00:03:34]
Wes Donohoe: so I started actually with my wife, my life now, she was my girlfriend at the time. we were in I grew up in Chicago sailing. I had moved from Delaware to so when I was 15. and so really got into sailing on the water. In Chicago. And then, my parents owned a small speedboat and so the worked out a deal with my dad that if it was always clean.

So if, anytime you want to use it, if the boat was clean, I, as a college student could also use the boat anytime that I wanted.  basically, it was the cleanest, smallest boat in the harbor. I was polishing and buffing on a regular basis. and while I was doing that, people would come up to me and say, Oh, you're a boat cleaner, could you clean some boats?

And so just literally at happenstance turned around and started then charging for boat, cleaning on the slip that I was on. and ended up then doing the bottoms of sailboats before sail races. So it actually get like scuba suit on, go into the boat, clean the bottom of the sailboat before the race, or, during the week, as a, probably the best job I had for a long time, in college, in a bathing suit out, on a harbor cleaning boats and making some good money was a, was it a fun, was a fun time as well.

[00:04:48]
Nikunj Kothari: I'm  sure you were a very popular kid for having the nicest, cleanest looking speedboat.

I'm popular kid After finishing in college with a major in entrepreneurship. In 2004. You decide to start your own company in the height of the financial crisis in 2008. How did you decide to venture out on your own in those uncertain times 

[00:05:13]
Wes Donohoe: so I, when I graduated college, I was, 

eager to start my own company. but I was also, growing up in Chicago 

and knowing a lot of the financial markets are derivative markets out of the Chicago mercantile exchange and it's cardboard trader was there. It was also a huge, exciting opportunity to go down that path.

I ended up going to trading versus starting my own company. and after a few years of doing that and having a little bit of success. Was able then to say, look like I've got some money, I've got some financial stability. I had, engaged to my wife at that point. and so it was feeling really an opportunity to finally take that leap, and go off on my own.

And I yeah started my first company. My first company was a fully weatherized touch screen that I put, by pools and on golf courses where you could order food while you're sitting on the golf course. You could order food from the little restaurant or the main restaurant, and then have it delivered out to you, or you're sitting by the pool and you could say, Oh, I want this item.

And then it would deliver out to your, deliver out to your seat where you're sitting by the pool. And so the idea was that it was, it took me all around the country actually was out in the Bay area. This is how I started to fall in love with San Francisco. I was actively trying to sell a lot of the country clubs in the Bay area

then my thought was that if I sold at that level, then I could easily go down to the Ritz Carlton, the four seasons and keep going down because I had started at the top of the echelon. and yeah, I did that for three years. I tell people that I was addicted, I was addicted to the sale or addicted to it.

It never took off, I probably should've shut it down after the first year to be candid with you. on the phone I would call people in a club would say, Oh, call me back next month or call me in three months. That's when we're doing our, either annual planning, our next member board meeting.

and Oh, could you come out to the club and present? And so those just little like highs along the way just kept me going and saying, Oh, I got to stay around for three more months or I get a sale and I install it into that one club. And then I would say, Oh, now I'm going to easily sell all of the other clubs around me.

And so I would park myself. I was in the Bay area for a few months, actually just shopping my product around the different clubs. and it would, they would say to me, Oh, come back out. in a few weeks. And I would, that would just fill me up for that few weeks to then try to get to the next club.

but it just, it never really got off the ground. And I kept internalizing telling myself constantly just, that one month later you just stick it out one more month. in my, another story on this topic is, the family and friends are like, remember that, startup company that.

Was going to close and then they got that big deal the last day before they, the day before they were going to close and rest is history. And now it's a fortune 500 company. It was like, everyone was encouraging me to keep adding, keep persistence. So I had a great, community of people helping me and supporting me.

and that, kept me going as well. So yeah. 

[00:08:31]
Nikunj Kothari: You talked to us a little bit about it. But tell us more how you were surviving and keeping yourself motivated

[00:08:39]
Wes Donohoe: it was dark. In times and had a lot of ups and downs along the way. there, the reality is that  I have a fantastic support with my family and my friends. I had friends that were, doing really well or different stages and, buying homes or moving to the suburbs or.

getting those significant promotions around me. but I still, I have this kind of glasses half,  half full mentality that I was, this next thing will work and this next thing will work. And so I was always excited about that opportunity and I had a good foundation that you know I could do it. I was, I was laser STEM on spending money, living in Chicago. And then, when I moved out to San Francisco, I lived on my friend's couch, for several months. And really just keeping my costs low. I was not the typical late twenties person, running around and then spending money.

Cause I just didn't have it. And, my excitement was in my, my joy was trying to sell my next thing or sell my next venture, get my company off the ground or, that's what was that's what was my excitement was my hobby was my, you're a stimulant of choice versus, a lot of other things that, definitely all of my friends around me were doing. 

[00:10:01]
Nikunj Kothari: So you would wrap up these ventures and then you decide to work with some of your past coworkers at live nation labs. In 2012. You make up your own title as director of analytics. Tell us how you transitioned from that role to be the head of product there

[00:10:21]
Wes Donohoe: Dan Rommel, who, you know, and, is someone that I've done multiple, ventures with. And it's, an engineering leader here at one medical where I am now. we had started a company and, we had disbanded the done after the 2012 uh election.

And, Dan was getting heavily recruited by live nation and joined and lead their, engineering team within this group called live nation labs and a loan. He was saying, you got to bring this guy Western he's amazing. You'll love him, bring him on. And, they will look at me like, what do you do?

what do you mean? You're not a designer. You're not an engineer. I have no idea what product management is that point. and so it, I never really fit. And thankfully Dan convinced them that I was the right person to hire because honestly I didn't interview with anyone. I had a few conversations with some of the heads and they said, okay, you've got Dan that's vouch for you.

And so they put me in and they're like, I guess West is going to figure out what he does. And it's honestly what happens. And so the HR person that, this fortune 500 company now, Emails me and says, what's your title? And I said, I probably, but I put director of analytics. cause I was like, my job is me in analytics and I don't know, director sounds like a great title.

That would be a fun title to have. And lo and behold, a few months later, I do find out that I wasn't doing well and some success there.  the head of the group is, Gavin and Eric Garland to separate means is okay. I can't believe you told him that your title is director of analytics.

And I was like, what do you mean? No one told me what my title was. And that's how I got into it. but then, I was in that role in the analytics role and where I've always, the mentality that I've had. And so I've to this day is how do I find value?

How do I add value to what I'm doing or add value to the company? And so I had access and was doing all of the analytic work at live nation from the conversion funnel on our iOS, Android, and web apps. all the different properties that the live nation brand did. And so I started then saying, Oh, I'm seeing opportunity and increasing the conversion funnel and increasing the booking flow to sell more tickets to the next greatest, Beyonce show or Jay Z show or something to that.

and so I, one day plugged in some JavaScript of Optimizely signed up for a free trial. And, just started running the experiments myself with jQuery and my janky ability on coding. and basically just started manipulating the conversion funnel, in booking tickets and actually had a lot of success doing it.

Yeah. And so that, then, took me into, Oh, okay. what is it doing? How is it doing this? Wow, this is actually pretty impressive on how effective, some changes are. And so then I became a product manager for the first time leading all of the, the web app at first. And then, within a few months after that actually overseeing all of product development, design, and a little bit of user researcher for, all of the live nation digital products.

So  it was a quick transition from analytics to SVP a product, doing some kind of leading, a fairly large team impacting all of our digital products.

[00:13:39]
Nikunj Kothari: How was that transition from working on your own small company to managing cross-functional teams? Like engineering product and design

[00:13:50]
Wes Donohoe:  yeah. the nice thing that I had and the attitude that I think I took was that I knew what I didn't know. And I learned a tremendous amount from the designers. I learned a tremendous amount about product managers. And so I would then just turn back and say, okay, what can I do to make them better?

What can I know alleviate barriers for them? How do I solve problems? amount accelerate and set them up for success. and then I'll learn from them actually. How do you do this job? Like candidly, like I was pretty apparent about it. at one point in time, I was appears with some of those people and then I became their boss or their boss's boss.

and so are the management managers. it was a pretty significant change. And so I had to very quickly show value about why I'm in this position, and what I can do to make their lives better. And that's a kind of controversial position, Being in a peer and then being their manager.

And in some situations I was at the managers of them. the nice thing, yeah. With the group that I was in, we were still relatively small in the larger ecosystem of live nation entertainment, which is a fortune 500 company. but one of the things that I loved doing was that I would go With just, okay, how do I add value?

One of the biggest areas is actually communication with the concert promotion team. And so we, as the team ran all the digital assets that drove concert sales and drove engagement to concerts. And then on the flip side, there was another part of the organization that. Was responsible for actually promoting concerts and driving sales.

and then there was another group that was for  putting on the shows in the venues. And so I just got on planes and just started talking to all of them and saying, look like, there's a mismatch between us as a group. How do we, what can I do to align incentives? What can I do to, what can I bring back to the team to help alleviate an acceleration things for you all for us?

because we had all, we internally on the team we wanted to bridge those gaps. No one was able to, and so I was like, that's an easy win. I can get on a plane and talk to people and bring, influence and comradery between groups. and so that was the first thing that I did first.

and, it added a bunch of value to the team and, we were able to see, even compounding effects on the products that we were delivering. 

[00:16:07]
Nikunj Kothari:  Did you ever have imposter syndrome? And how do you end up fighting that for the days that you did

[00:16:15]
 Wes Donohoe: no, cause I'm like, maybe other people would say this, but I feel like I'm just like a pretty, I'm an open book. syndrome know anything about that. Like I would rather communicate. I That I didn't know, and learn and then say, okay, , here's where I'm going to add value.

So I think that allowed me to, and has allowed me to  get smarter faster, because  when I've let my guard down and I tell people I don't understand. and, And they're comfortable with that. And I'm able to, they're able to like, and then I'm actually able to learn how they're thinking and what they're doing.

and so   I've always tried to just be frank and transparent in my capabilities at that thinking what 

[00:16:57]
Nikunj Kothari: You're leading product at live nation. And also advising companies on the side. One of them is Shyp and after a while you end up eventually joining as the head of product there. How did that transition happen 

[00:17:12]
Wes Donohoe:  dan and I followed Dan anywhere.  All kidding aside. it was really that he introduced me to the company.  we, we both joined live nation. he'd left live nation to go to ship, be their CTO when it was that seed or kind of pre-seed rumble company.

And at that point in time, he asked me if I'm interested in, talking to the team and getting to know the group and, I was not ready to go and leave a company, a kind of a stable income, honestly, like at that point in time in my life, it was the first time that I was getting like a stable income.

 had actual sustainable money. It wasn't the bare minimum just to pay my rent. And so I think my wife divorce me if I was like, okay, now I'm going back to it. but we just had a kid as well. So like stability for me was. important that I was over-indexing to stability at that time.

but  I'm in the Bay area to, take big leaps and big opportunities and big, risk on new ventures and new opportunities. And actually figured out a way to scratch both itches. I started advising initiatives doing about 10 hours a week, where I would, the ship office was down the street from live nation office.

And I would either go in the morning before work or after live nation. I'd go over to the ship office and I'd spend a bunch of time working with, the founding team and Dan, and as that team started to grow that the rest of the group on various different initiatives across.

Product and sales and analytics and engineering, and, built up a great relationship with that team. I did a year of that, so it was fun to off and on for a year.

[00:18:48]
Nikunj Kothari:  You were at Shyp for a few years where you saw a lot of innovation happen, both in product and in the warehouse. What was the biggest challenge you think you faced at Shyp?  

[00:19:01]
Wes Donohoe:   I got a taste of this at live nation, which was the, Starting to do things that were just not  all digital. So a lot of separate LiveNation the after you bought your show, how do you get to the show? What do you do when you're in the show? and then when  I went to ship it, just put things through that thing on steroids.

And so is there really exciting time to be able to thinking about is it, technology enabled or technology power to the different words that get thrown out a lot now? where we were an operations business, delivering, picking up packages and shipping packages, but we were, accelerating everything through technology and creating a kind of differentiated and fantastic experience with tech.

 Oh, yesterday. And this guy was like, I can't believe you a chip. I loved ship. I loved to ship. There was amazing product. I get it to this day and age. it's a Testament to the team that did everything there.

I think  the biggest lesson that I learned, or the thing that I learned in the challenge I learned is that we had a product where every single day we had a core group, people would tell her that they are absolutely in love with ship. Yet our economics were set up for volume. And the way that we were built was set up for volume.

not like high volume, high turnover business. And so we priced it that way. We thought about it that way yet our users that loved it, used it one or two times a year. And so we just didn't have that. We really didn't see it for a long time, honestly. Like we were blinded and I was blinded with, wow, this people love this thing.

Okay. Let's just go find other people like this that love it. Or let's try to build certain initiatives to get. To introduce it to different people because they're going to love it too. and instead of doing maybe like a hard pivot, which we had talked about early on in the company's formation, hard pivot into more of a, an eCommerce seller or a, B2B business.

 I hired someone on my team, to join and lead partnerships. And so him and I  went down to eBay, and we had a product manager and a small little team and me, we establish a pretty deep integrated partnership with eBay.

And we were excited about it, but we just didn't, we didn't over-index and we didn't over-index on that investment. We were doing it off the side of our desks, because we basically had everyone every day, we had a slew of people just telling us about how much they love the product 

[00:21:22]
Nikunj Kothari: Yeah. I remember those days. Where we were trying to pivot. But we were seeing some success, but not enough. You ended up leaving ship after a while. How did you decide what to do next 

[00:21:37]
Wes Donohoe: yeah, so I, I took a little bit of time off, that was that, a kind of bitter end as that thing went up and then came down. and so I  leaned on to things that I'd started to really love. I started to really do some self reflection and realize that I love the idea of.

Physical and digital, how do you leverage technology or bits announced any move, different things around. And so how do you leverage technology? and the physical service design element and combine the two to make truly transformational products and experiences. And so that was, for me, it was a cornerstone.

the second one was I wanted to get into healthcare. my parents actually, my dad was an EMT and my parents started an ambulance company when I was a. Before I was born. and so I did also some self reflection on, what industry do I want to work in and what do I want to work on? And, I kept coming back to that.

I had worked in the shipping business, the entertainment business, the, the country club business, the food and beverage business. I was all over the place. And I said, okay, I want to find something that is physical and digital. and I want to find something that's in healthcare.

And, I looked and, one medical, lucky enough was a fit both of those criteria and they were willing to hire me and I, was off to the races from there.

[00:22:53]
Nikunj Kothari: How big was the one medical team when you joined ? 

[00:22:57]
Wes Donohoe: No started their team was the product team. At that time. It was about six people, maybe a little bit less. and, went through the craziest ride upswing that I've ever been a part of. team almost 10 acts as a product team, of of product development and technology.

10 X as well, along the way.  we're moving from five-year-old soccer to, more of a professional sports team where we were going after different things and more of a balanced approach. we did that through, really leveraging technology to drive significant impact in the organization and give the organization scale.

and so when we started. We didn't have that really model figured out . technology. It wasn't used as, and seen as a way to accelerate the business or to deliver a positive ROI, in some situations that could accelerate the business forward. and we weren't very good at, hitting deliverables on time.

There wasn't a lot of confidence in the organization that if we said something, we were going to do it in  a reasonable amount of time. And we got those two nuggets working and got that flywheel going. And so just kept putting more money into technology and kind of saw that, payout over those four and a half years that had been there.

but it's been a, it's been a crazy ride, during that time period, I've had multiple. Executives and multiple friends, kind of turnover in the organization. we've had a new CEO at the time and, someone that I truly respect both Tom and Amir that are there, but, going through that as the company is growing and replacing different key executives had.

Had significant, impact on their, the individuals in the organization. and then, from the outside it's looked like, Oh man, this thing has just gone up into the right the whole time. But, throughout that experience, there was definitely some massive highs and lows as we were going through it.

[00:24:47]
Nikunj Kothari: What innovations has one medical brought that you see are being copied everywhere?

[00:24:52]
Wes Donohoe: It's no secret that digital health or just digital 

health specifically as a category has just exploded in investment.  So healthcare is close to 20% of GDP. You throw a dart anywhere and you're going to hit a billion dollar industry. and any sliver of the healthcare ecosystem, is bigger than most than the significant portion of what other industries would people then total Tam is that people are looking at.

and so I think. you know, it's always been a competitive space. It's always been companies coming in and trying to replicate the one medical model, either in healthcare or either in the dental until industry, the pet industry or other things within the space. you've also seen parts of one yeah. Medical that have spun out and people have gone after and tried to unbundle a little bit of the services that we do.

there's a lot of incumbents that are in this space because it's a massive part of the overall Mark, the overall economy. and I think it's just heating up, which I think is great, which I think is actually a fantastic opportunity.

[00:25:56]
Nikunj Kothari: COVID happens early this year. How does one medical respond to it?

[00:26:03]
Wes Donohoe: So we went public on January 31st of this year. we were in New York city, we got listed on the NASDAQ. We were in the NASA bell. There's a bunch of us that were there. and then I flew back with a handful of people back to San Francisco.

basically left a little after 11 o'clock hopped on a plane, flew back, to make it back for a party with our team and our families. And, so that we could celebrate here in San Francisco with our group. And, we took the Bart back from the airport, and while we were on the Bart, looking on Slack and looking on phones and seeing how things are going and realized that in LA, we had a potential outbreak COVID in our clinic, in one of our clinics and our providers we're top of mind, how do we keep them protected and safe?

How do we keep our administrators? Yeah. And our admin staff at the front desk safe. and also how do we keep our members safe and how do we help navigate them through this challenge? And The next day on Saturday, there was a, task force set up and they were running and it started to run seven days a week . And from a high to a low, we basically are a high two. Oh my God, what's going to happen. And what's going to happen as this thing is starting to hit our shores. and so honestly,  what we did from a technology perspective is fairly little, we as a operational and clinical organization, and a, human, people team perspective, put a majority of our effort there.

we didn't know what was going to happen next. and so we were reacting a day by day, changing standard work staff, changing messaging, changing clinical protocols as we went, the nice thing on the technology side, because we built everything in house.  we just started customizing  through configuration.

as a great example, we have a survey tool that we were using. To survey our patients. we just turned it the next day and to COVID questionnaire. and one of the first organizations that have. The COVID symptom screeners, we  had testing, launched very quickly to the, to our first earnings call.

We announced that we did close to 2% of the nation's wide testing and we are a fairly small footprint as an organization. but we were able to flip on and start doing COVID testing, because we had the supply chain. We had the infrastructure. We took our offices and we just converted them into COVID testing.

we weren't coming in for primary care visits, so we flipped them into COVID testing and then started doing drive-bys dry drive through center. 

On the tech side it was fun because we were like, okay, how do we configure? how do we change and do all remote zoom, like video visits versus asynchronous or versus in person.

how do we take things that we capabilities that we have today and slightly augment them, to be delivered in a, a hundred percent virtual visit virtual world and in many situations. and then we're building up on the tech side. Okay. Here are the things that we're going to start.

If these here are the things that we now need to start investing in, or are doubling down on to sustain going forward. but we set up what we have kind of reaction teams inside of the group where we just disband and rechartered teams on the spot. We have a process to do that. and so it was a kind of the highest high to the, Oh my God.

I have no idea what's going to happen next within less than 24 hours. 

[00:29:27] 
Nikunj Kothari: What changes do you expect to stay permanent even after covid is over?

[00:29:31]
Wes Donohoe:  it's been a massive catalyst for change.  I think in the, in the healthcare space, one of the biggest problems is access. one of the biggest challenges of getting to see a primary care doctor getting into an appointment, has been access related.

it's been transportation, it's been availability of appointments. It's been appointments at times that I can do and leave my work to go do it. It's not just nine to five. And so I think what COVID showed us is very quickly is that, People are willing to do their, appointments virtually and not only willing, but love it.

and so you can actually use that one of the biggest problems in healthcare of access. actually we've been able to prove that you can deliver care in a virtual setting very efficiently. You can start to use more connected devices to do more things in home. And all of those things we had to put on accelerant.

because we had to with COVID and we're seeing those work and we're seeing them solving a bunch of access problems. and that's an area that is really exciting, that I think is a, been a fundamental problem within healthcare for a long time. And I think all the innovation that's happening out of COVID is gonna help solve that.

I think the other side is that, maybe the other side is that. Employers for the longest time were just offering insurance and just covering insurance for you. But now they're realizing, it's not just insurance, it's more, it's mental health. It's, COVID testing, it's screening protocols.

When you come into the office, it's, distancing and thinking about, as a, as an employer, you're taking care of your community and how you protect your community. And we've seen a significant growth in that market that we've told publicly, this is not private.

We've told this publicly, that our growth and our kind of selling one medical as a benefit to employers, employees has just accelerated. and I think it's a mind change with our, employer customers that they're seeing that significantly, whereas before it was. Y o u know few organizations that were thinking about that whole wellbeing, we're doing a lot, but now across the board, every organization, every employer now needs to not just think about, Oh, I just need to give my employees insurance, but how am I taking care of them, their whole self.

And so it's opening up the mental health space. It's opening up, muscular cirrhosis and looking at really fundamental problems with their employee base. and, COVID testing included. I'd say those two things are pretty exciting to me. It's a huge opportunity, to solve some big, fundamental problems that have been, in the healthcare space for a long time.

[00:32:04]
Nikunj Kothari: I always like to end the show by asking our guests. To share a time that felt like a roller coaster. And what did you learn from it 

[00:32:12]
Wes Donohoe: the example that I am going to give you is back in 2008, and probably late 2007, 2,850 exact timing. But, I had just, decided that look, I'm going to start my, my kiosk company. and I had a really good friend that was a trader that left.

trading firm and was saying, I'm going to S he's going to go start his own company as well. And, he had a little company that was in the kind of student loan space that a venture capitalist in San Francisco had acquired for a little bit of money and said, Hey, but I want you to come and help.

help our other portfolio companies and some of the stuff that we're trying to get off the ground. and so he started as a kind of consultant and employer, this company called the point. And so we're in Chicago. And so we meet up and he's Hey, I'm working with this company. The point I'm super excited.

I've got this idea that I need to figure out how to teach people how to use the point. And I'm going to do it as a group. We have his tipping point concept, but I'm going to do it for coupons. And I'm going to sell to organizations and businesses. That, if we get 50 people to agree to buy this thing, it'll tip and then everyone will get it.

And. He's I'm going to sell these coupon business and I'm sitting there with them and I'm like pitching them on my kiosk business and this thing's going to be the greatest thing. Look at all the stuff we're eating lunch and, excited. We're both on our highest high, we're eager about what's gonna happen in the future.

But I constantly kept telling him, I'm like, you're going to sell coupons. This is literally what you want to do. This is your grand plan. I'm like, this is nothing. I've got this great, this kiosk, I'm going to build this hardware. And this is going to be fun. that next year, that coupon tipping point turns into Groupon,

they changed the name, from the point to group on. and multiple times he asked me to join his company to say, Hey, come over, join group on this. Thing's working out. Yeah. We are only doing a few deals in Chicago, but it's growing like mad and I'm, on this, internal, like nothing's working, I'm trying to sell, my kiosks and I'm going to get someone to call me back and thank God one.

Person's going to call me back this week and I'm going to talk to him. And And then I'm seeing my friend and multiple of my friends. Cause he then starts hiring all of his other friends, just join the greatest rocket ship at that point in time, explode in Chicago. 

And, I, at that other point was, still positive and still excited and, trying to keep this thing on. But at the corner of my eye, I'm looking at someone that I was like,  Oh my God,  they've just been a part of something that would be the greatest thing in the world.

And so it taught me a lot that actually I, that is going to come and it's going to happen. And you know what. I can't get jealous or I can't get mad or I can't get anything like that. is I'm singing my own tune. I got married at that point in time. I was, I had a lovely family and life and was healthy and was happy.

and I really never. put it never got too far down that like envious road. and that was probably the toughest point of my career of trying to do that. But it's actually been the thing that has held me together as I've done every different venture and every different opportunity with different people,  I have tried to kept an even keel and know that  other people around me are probably going to do, either have wildly more success than me that I'm really close with and I'm friends with and I missed out, or vice versa, people are gonna look at me and say, wow, I can't believe this is what, I have accomplished, and I just have to realize that  I have to be true to myself and be confident in myself, and know that I've had the support around me,  I remember I'm like you, when it's sell coupons, I was the dumbest person in the entire world at that point in time to be like, this is the worst  idea possible. 

It was actually something that I reflect on a lot to make sure that I ensure that I staying true to myself and keeping myself centered and moving forward. 

So Yeah.

[00:36:03]
Nikunj Kothari: That's a great story. With that I want to thank you for taking the time and sharing all your highs and lows today. It's been really great chatting with you 

 [00:36:14]
Wes Donohoe: All right. Thanks so much!