Tito Goldstein: Orchestrating Efficiency with TeamBridge

Jake Aaron Villarreal: Welcome to our podcast, From the Ground Up, where we interview startup founders exploring their journeys, their successes, challenges, and lessons learned. We hope you be inspired in discovering what it takes to build a thriving startup. I'm your host, Jake Aaron Villarreal, and here with us today we have Tito Goldstein, a funded startup led by General Catalyst. And also one of the first product designers from Uber that left to start TeamBridge. It's a fascinating story. Tito, welcome to the show.

Tito Goldstein: Thanks Jake, thanks for having me.

Jake Aaron Villarreal: Great. So a little bit about Tito. Tito is uh not just the co-founder but he was also one of the first product designers at Uber building the application that we all have used and love today. Tito, before we dive in here, for people that don't know uh your experience about Uber, walk us through how you found out about Uber and, and why you originally joined.

Tito Goldstein: Yeah, so I actually ended up taking one of the most entry-level jobs at an advertising agency just so that I could network and you know find really cool people to work with. I started working nights and weekends hacking away on a messaging product with two engineers. And that was my first foray into product design. I just filled in the gaps between what was in my head and what the engineers needed to build. That experience helped me land a job through AngelList at a fintech company down in Los Angeles. And actually, I think it was like my birthday or something, but I got a call from my eventual manager saying "hey, I saw your portfolio on Dribbble," which is a show-and-tell for product and design. And he asked me to come up and do an interview.

Honestly I hadn't been a huge Uber user even at that time. Um and actually in my interview at Uber I met my co-founder Arjun. Um and we became a pair and a SWAT team that really worked our way through many different aspects of the company because back then it was kind of the Wild West where whatever the lowest hanging fruit is, you know that was the problem you needed to solve. So it was really exciting to hear from this company that was definitely making a name for itself and to come up and be validated. Considering I had never really had a product or a design you know job prior, and I had never taken a product or a design course prior to taking that kind of senior position there.

Jake Aaron Villarreal: Wow, that's amazing. So is your background in development and then you became sort of a product design person, or what was the makeup of your, of your background?

Tito Goldstein: I think my background is kind of just like a tinkerer. Um, I studied International Relations in college and I knew that I probably wasn't going to use that, because that normally means you're going into a poly sci NGO type of environment. And I was much more thinking about "what can I create, what can I build?" But I wasn't an engineer. I would hack on things. I think in college I created a script that... sorry to all the folks I spammed... would spam a lot of people on Twitter before the API had limits, and it would ask them "hey, are you looking for someone to manage your social or digital mark- marketing?" And that helped me pay for a lot of college actually. So it was like this you know mindset of possibility, but also I didn't have, to be honest, the full range of skill sets. And that's when I started really just using the modern tools. I think Sketch was a, a recent development back then before Figma, which is the most popular now. Um I started picking those up and I, by, by nature of using those tools I was able to outpace a lot of the people in you know Illustrator and Adobe because these tools were designed for modern, quick iteration web design and prototyping. So it was a lot of cool stuff that I was able to jump in when it was brand new and then just leverage that you know plethora of information on the internet to just start learning and building those lingo gaps uh to get into that community.

Jake Aaron Villarreal: Yeah as you, as you were at Uber, you were there for some time. How long were you there, and does it really match up to the miniseries some of us have seen, Super Pumped, where you got Travis Kalanick resembling this you know bold leader, he was out there you know confronting issues and taking names? Like, give us a little behind the scenes of what it was like for you and what you saw.

Tito Goldstein: Sure, so I was definitely there pre- and post the 2017 drama. Um I will say that that show is obviously dramatized in such an extreme way. I think there's text flying across the bottom screen you know with frat type language. Um I wouldn't say that the nuances of Travis as a person are captured. A most obvious one I think I saw was the Vegas presentation on the cultural values. Now he was up there, very proud of these cultural values, but he was a nervous presenter. He wasn't you know throwing or unveiling things you know in a flamboyant way. Um so he definitely wasn't that loud um persona that Joseph Gordon-Levitt plays.

Um I think Mike Isaac's book that that Super Pumped is based on is really well researched. Almost everything that you know is in the show happened, but it usually happened in a much more subdued, d- way. Um Travis was not often in you know an office, he didn't have like a big central office in the, in any one of the offices I worked. And he was usually like pacing and thinking and pulling people into you know quick meeting rooms just to like have a discussion. Um but he was a really amazing product thinker. Um he was someone who very clearly could get the concepts um both of the market and the nuance of specific features really quickly. Um and that was something that you know helped Uber stand out even in an aggressive space where multiple um companies were vying for this opportunity.

And then one thing I really like about the show is how much it really shows Austin Geidt um and her ability to launch a city, which was the reason why Uber had so much success. It was that operational efficiency and that operational drive to go into a place where you didn't know what the compliance would be, get drivers up and running, help support them, build that community, but also aggressively go after that market. Like even China, um which was my first week, three weeks in Uber I actually went directly to Beijing and started interviewing drivers there to figure out what Didi, our competitor there was doing that we weren't. So it's really interesting from a product perspective to be able to uh bounce around between all those different cultures and have to build a product that was ubiquitous across them.

Jake Aaron Villarreal: That's amazing. As your experience at Uber grew, was there one mindblowing innovation or breakthrough that you recall before you ended up leaving and, and starting your own company?

Tito Goldstein: So one of the first things I did, which was actually sitting at a restaurant on a rooftop after a 16-hour day interviewing drivers. It was me, um Jeremy our PM, and Arjun, my eventual co-founder, but I had just met him. We were just brainstorming what's the lowest hanging fruit? Because a company like that that's innovating so much has often a lot of low hanging fruit, but people get lost in the weeds with you know their individual products. And the first thing we thought of was "why isn't there in-app chat? Why can't you message your driver?" Like this is such a obvious moment of friction when you're trying to find the right car or you're trying to tell the person what your driveway looks like. And so we set out to build that feature. Um we ended up launching that feature. It ended up saving the company hundreds of millions of dollars sometimes in just SMS fees alone, because everything was falling back to SMS. Um and also it helped reduce cancellations across the board. If you think about in a market like Indonesia, if you miss that turn it might be 45 minutes around the block in traffic, so that is a big missed opp- opportunity to have like a successful pickup.

And I think that that was a little bit of friction even getting that shipped, because back then they thought "hey this should be a magical experience, it shouldn't take any manual effort to be able to you know get the driver to come to you." And GPS made that the case a lot of the time, but the truth is communication is a great Band-Aid you can call it for the 99 you know percent of the problems that you're going to have. So it helped give those tools and leverage the platform and bring it all within the platform to provide things like translations, quick replies for drivers so that they're not typing, um audio like voice notes. And there's many more features that they continue to ship that were on the roadmap that we built long ago into that feature. So that was really I think the first feature where both Arjun and I started realizing: even if you're not tasked with this opportunity culture, the culture at Uber back then was very much a startup and anyone who did the work owned the product. So we were starting to you know get our tentacles into both rider and driver by building that cross-platform feature.

Jake Aaron Villarreal: You know, many won't experience the ride of building a company like Uber, but being on that rocket ship, I'm sure there's experiences you walk away from and you can apply to your own companies that you build in the future. What's one experience that you look at that you're applying today to your startup?

Tito Goldstein: Yeah, I mean going back to kind of your initial question or talking a little bit about the drama of Super Pumped, I think both Arjun and I were privileged enough to see the culture of Uber before like all that kind of blew up in you know the company's face, and also see the culture after. And I think that allows us to pick and choose the stuff that we really loved about the before, also identify the things that didn't work and led to that drama, and then look at the kind of maturity um of the after, but also some of the limitations there.

So if you think about Uber in the early days, that ability to go out and take on a challenge that no one asked you to do, and be rewarded for it, was really important. And I think that's something that we want to empower every single one of our employees to always consider when making a decision. Like what is the lowest hanging fruit? I don't need to necessarily ask for permission if the cultural values and the intention behind what I'm doing are driving that customer obsession and driving that experience and benefiting the company and its culture overall. And on the flip side making sure that you know, we are adhering to those cultural values and not weaponizing them. Not letting them become something that is uh a negative force because people are truly toe-stepping on other people's work or pushing other people out of the way. Um so I think that there's that fine balance between that meritocracy compared to that toe-stepping.

Um whoever's best idea should win, but it should be a principled confrontation where we're coming together. And whether it's like you know an argument for the sake of "we believe that this will make the product better, this will make the feature better, this will serve our customers better," um if we're coming to that, that conversation knowing that each one of us just wants the company to succeed and wants our customers to see value, then oftentimes we're going to come up with the best solution. So I think that there's cultural values that you know Uber and even Amazon and some of our other employees have pulled from companies like Facebook, Google, um Slack um, that we have adopted, but making sure that our cultural values aren't weaponized and that um we have kind of that you know benevolent intent. Because ultimately if our customers are happy you know, they're going to refer, they're going to grow, their- our business is going to succeed.

Jake Aaron Villarreal: I love that. Yeah, culture is important to build it from the ground up, so sounds like you're on target with that. Um let's shift gears and talk about your current startup, TeamBridge. What inspired you to create what you're building today?

Tito Goldstein: Yeah, so obviously it was born out of kind of this, me and Arjun's time at Uber. We had the privilege to talk with thousands of drivers all over the world. And they weren't telling us they were leaving their more secure, more consistent jobs because they were making more money at Uber. In fact, a lot of times they were making maybe a little bit less. But they were actually able to operate with a much higher quality of product. They weren't you know going to some HotSchedules spreadsheet on their phone and zooming in trying to find when they had to show up at work. And if they missed something or misread a time, they would show up late and that would create friction. They were actually able to open up their app, click "let's go to work" and start following instructions in a very clear way. They also were able to control a little bit more of their schedule and their time.

So when me and Arjun started thinking of what can we do with this knowledge, what can we do with this experience that we have here, we started thinking about 80% of the world's workforce which are hourly, and the quality of tools that they're expected to use every day. And we thought, in fact most of these people require their tools to be better than your average white collar tool. Like Workday and some of these other tools, we might only go into them once a year as you know a desk worker. But these folks are using it every day or checking their schedules and it's highly variable. So we thought they deserve a higher quality of tool, and yet they're getting really poor tools because honestly the folks who are building software, the folks who are building this technology probably don't understand this market very well. So we had that unique perspective of being able to talk with all these frontline workers and the tech, tech talent to be able to ship products. So we thought that fit really nicely and we started working on you know these flexible building blocks to tackle many different industries in TeamBridge.

Jake Aaron Villarreal: It's interesting. You know, prior to the company I have today um we had built a contract staffing company. And the experience that I had was you know, I had came from Oracle so I was selling technology and it was very high performance technology we used internally. But when I got into the staffing world it was very different and I was always frustrated with the types of technologies that were being used and very archaic and not integrated and just, it was frustrating. And with a little bit of luck and and and growth we, we, we fell into a position where we were able to get acquired in a really good way. But I always felt that experience of working in staffing wasn't great. Now if you look at the industry today... 20 you know '22 last year, it generated 168 billion in revenue. Um and you would think with all the revenue and innovation going on that there would be true innovation in this phase. When you're talking about putting hourly workers on billing at a company, or just as an ent- maybe you're hiring a lot of 1099s, that experience just doesn't exist the way you would think it should. So I understand the problem you're trying to solve. I think it means a lot and uh I think there's big opportunities with it. Do you have a niche carved out that you're offering this to, or is staffing one area but you're looking at venturing into other categories as well?

Tito Goldstein: Yeah it's a great question. So when Arjun and I started building TeamBridge we actually, we were well aware and that we didn't understand many of the industries we were selling into. So because of that we leaned on our product savviness and our industry lack of savviness, and we've built it very much modular and flexible at like its foundational level. Now whether that was strategic or without serendipitous, that resulted in a couple things. One, when we went into a demo we were able to just ask "Hey, what's important to you? What are you spending too much time manually doing?" and then build with our building blocks and our Legos the automation that matched to exactly what they needed. That also meant that we weren't really tied to any specific industry. Now that being said, during COVID and you know even to today, staffing is such a you know massive industry that you pointed out with those revenue numbers that we kind of fell into a couple big clients in staffing. And those, those clients became design partners, because they're really feeding me and Arjun you know product direction. They're saying "Hey, you know this would be really cool, this would be really cool." And we just take it and we start thinking "Okay, how do we create a platform feature around that that not only unlocks what they're talking about but also unlocks many other industries?"

So to your point, staffing is a huge piece of our business, but we do have a long tail of many other industries. And we're constantly like deciding and figuring out and hearing feedback from those design partners to see if there's something we think would really unlock those industries in the same way that we've already unlocked staffing. Because of all the back and forth between the client, the agency, the labor pool, and that back and forth typically is, is not something you know, a standard scheduling, time tracking or just even a job board uh product could provide. But in TeamBridge you can create all the unique access profiles, all the unique automations, all the unique mobile views you need to really unlock whatever workforce workflow you desire.

Jake Aaron Villarreal: So if I'm an employee out there and I'm an hourly worker, what's my experience like? What do I look at when I'm going to work, what am I leaving with when I leave work, and what's the experience I'll have that's different than you know hitting a time you know, clocking in and clocking out with a time card?

Tito Goldstein: Yeah it's a great question, and again we focus so much on the modularity of that, that one, an employee at Company A might have a very different experience than an employee at Company B. But your typical modules that you can interact with would be onboarding tasks, compliance documents, signatures, getting all that HR stuff out of the way very simply on the top of your mobile screen. Being able to view opportunities, whether in staffing it's contracts or shifts, or, or even just view my schedules if you're at like a more traditional uh model where you're a full-time employee. And then once you uh are ready to work you can go right into our time and attendance platform, which can be on-site, device agnostic, or with our really cool mobile time clock, which is I think where most people are going because you've already got your phone in your pocket. You can walk into the facility, the location, the store, click "clock in" (we already know you're there from the geofence and the geotagging) and you can even create custom fields and requirements at each step of the way. So you can do little micro-scheduling moments, or just require a signature or a clock out note, or confirmation that they did a number of tasks when they left the facility. So really like it's, it's hard to ever say exactly what the experience will be because instead of us force-fitting a company's workflow to our tool, we say "Hey, what's your perfect process? Like what are the things that you wish you could do if you had an infinite workforce or an infinite number of admins keeping everyone on the ball?" And we say "Let's go ahead and automate that so that your policies are automatically enforced and you become the fastest, most accurate version of the company you want to build."

Jake Aaron Villarreal: Wow that's amazing. You were founded, if I'm correct here, in 2020. Is that accurate?

Tito Goldstein: Uh right before COVID started, so um yeah I mean we officially probably jumped ship in 2020.

Jake Aaron Villarreal: Yeah, okay. And when you jumped ship you raised capital from General Catalyst, great company um you know, behind Airbnb and Stripe and a number of big companies that we all know. Um in the market today it's tough to raise capital. What was your experience like raising capital?

Tito Goldstein: Yeah it's a great question. I think that probably the market today might be a little bit more you know locked down, but I still think the market for seed and even A rounds is probably a little bit looser because those dollar values are smaller and investors are keen to get in early where, when the equity is at you know a, at like a discount you could say. Um Arjun and I planned all of our investor meetings in I think we wanted a two-day span, but it ended up being a four-day span. I think we had 27 total meetings with top tier investors here, all out in the Bay Area. And we had 25 term sheets um a couple days later. So we very much did it like a rapid fire like, make sure we get a few VCs who we know are a little more aggressive and willing to see the idea, see the mission, and jump in. Um and then once you have that first term sheet I think a lot of other investors are scared of missing that opportunity so they follow on.

Um so the process was very fast, it was very exhausting. I remember sitting at a cafe near Arjun's apartment at the time, both of us like nearly falling asleep into the sandwiches we were holding, cuz someone had told us that "throughout this process make sure to eat, make sure to drink water." And somehow we forgot that and we, we hadn't eaten or drank a single sip of water the whole day. Um and then we followed, once we kind of confirmed or figured out who we wanted to go with, we had a long tail of angel investors and strategic partners we wanted to meet with, um and picked a few of those to kind of complete the round.

Jake Aaron Villarreal: Um what keeps you up at night as you think about the future of TeamBridge? It could be opportunities that keep you up or challenges you see.

Tito Goldstein: Yeah that's a great question. Um and it's an interesting one because I think both me and my co-founder probably have different things as we've started to somewhat take on unique responsibilities versus the overlap we had so much as an early company. I think that there's a few things. I think one of them is just the company building aspect. I think that as we shift phases, my role existentially changes every 6 months. So it might be hiring, it might be sales, it might be onboarding, it might be admin work. Because oftentimes as a, as a founder you're doing the grunt work that you don't yet want to pay people to do, like "I can do the taxes, I can do this" and you just kind of do all that, so it just becomes this busy work. Um so I think that there's always that unknown, and we don't know what we don't know in terms of what's coming up next. That's always a little bit curious to me.

But I think that now that we're looking at where we are today, we've, we're going to 5X this year, hopefully we'll 5X next year in terms of our revenue. Um I think a lot of it is making sure that we can maintain that culture as we scale. Make sure that as we bring in people we don't let the quality and the bar for the type of talent density we have slip. Um and then from a more tactical perspective, I think because we operate in so many different industries, I think the curious thing is how do we make very smart tactical decisions about what we build, who we're building with, and where we focus our limited resources. Because we want to make sure we do right by our existing customer base, but we also want to make sure we take on the like let's call it lowest level level of engineering lift and highest value industries that are out there that we're currently you know in communication with or have design partners in. So it's a nice thing to be worried about that stuff because before it was worried about like "Does this company have a future? Will we be able to make it to the next paycheck?" But luckily we're a little bit past that hump and our revenue numbers are good and our, our sales are good. So it's been exciting to shift to maybe a little bit more, less of a stressful world here.

Jake Aaron Villarreal: Yeah that's great advice. Um what, what, what do you look at um I guess in terms of lessons that you've learned so far in this journey that you think is worth sharing with other startup founders that may already have a company, or might be an engineer or designer on the side thinking about building a company? What, what's a few I guess lessons you can share with them?

Tito Goldstein: Well it's funny because I think the CEO of NVIDIA recently went viral because they asked him "If you could go back to when you're 30 years old and do it all again what would you do differently?" He's like "I wouldn't, I wouldn't have started a company, it's a crazy thing to do." And a lot of me does agree with that. Um I think that the opportunities in tech and other industries to make quite a bit of money and have like a much more comfortable life are out there. So I don't know if I would ever suggest people to jump into this entrepreneurship capitalistic roller coaster that you are um committing to. Especially now with investment life cycles and the prospect of IPOing or cashing out or exiting being much longer than the 2020, 2021 days where you'd get massive valuations in a few years.

That being said, it's incredibly rewarding. It's incredibly fulfilling being able to have a sense of control and a sense of ownership over every aspect of what you do. We can hear a piece of feedback from a customer on Monday, decide we want to build it Monday night, ship it Thursday, and Friday our salespeople are now pushing that as the latest and greatest thing because it's direct from our customers and what they want. And that is such a cool thing when I know that at an Uber, at Google, a feature that we could do in a week sometimes would take six months. And even if it does take six months, they're probably going to experiment on it for a year because they're worried that it would you know reduce the sales of search engine advertising by 0.1%. For them that's millions and billions of dollars. For us, we can take those risks and we can continue to move fast and iterate and build what we think is the vision and the future of workforce management.

So I guess my advice would be if you do have that itch, if you do have that kind of lacking you know in your, your job or you see those opportunities, like definitely go for it. Understand that it is an emotional roller coaster, but if you're in the headspace to realize the perspective of how grateful you should be to be in that position in the first place, to kind of control your own destiny, like yeah go for it. It's, it's uh, it's unlike anything else. And it's really cool to you know hit each milestone and realize that you are now in the 1% of the 1% just in the nature of making it to that next funding round and making it to that next milestone. So I think my advice is "don't do it, but if you do, you know, make sure you maintain that healthy perspective that it's such a privilege to be able to go out here create something from scratch, creates you know something out of nothing, and then have a team around you who is evangelized by a mission that a couple years ago was just an idea on a piece of paper that you're like 'Hey, this could be cool.'"

Jake Aaron Villarreal: Amazing, yeah. That's super cool, and super pumped too. I'm super pumped on this man. What's ne-, what's next for TeamBridge on the roadmap as you look into 2024?

Tito Goldstein: Yeah, so I think we're uniquely positioned because we are so flexible and people can store so much of their own data and logic in the platform to take advantage of this recent AI wave. Um we're not going to create a generic version of the tool. Like um a lot of folks out there who just use their data and say "ChatGPT, go do something cool" and then it's not really a useful feature. Um we will be able to ship uh a lot of unique elements uh where we can automate repetitive tasks, which has always been our goal. So we're going to release a chat recruiter, um an omni-channel recruiting bot that will automatically reach out to new candidates, collect information, help them through the process. And then we're going to continue through the admin lifecycle to continue to leverage that AI in scheduling and, and time clock corrections. Um all the way through automatic invoicing, so we're going to have lots of cool features there.

But then we're also just going to continue to uplevel our platform. So every time we add a new automation trigger or action, similar to like Zapier, it unlocks thousands of permutations and we get to see how people leverage that. So I think we have a big push towards this AI stuff because I think it, it does present a really cool opportunity for our clients. Um we're going to continue to leverage marketplace fe-, features for our staffing clients and make sure that they can spin up really elegant, beautiful experiences for their staff, and they can monetize that uh placement of shifts and contracts really nicely. And then we're going to continue to just make the platform better so that all like the industries that use TeamBridge are going to be able to creatively solve their own problems in ways that could only be done by hiring more admins or spending millions to try to build your own tool.

Jake Aaron Villarreal: Yeah, that's really great. Well, as you look in the future here and others are listening, if they wan-, want to reach out and find you or TeamBridge, where do they go?

Tito Goldstein: Yeah, so you can always set up demos uh to see TeamBridge live at teambridge.com. You can also you know connect with me on LinkedIn. I'm pretty sure I'm the only Tito Goldstein out there so my SEO is usually on point. If there, if another one pops up anytime soon I'll have to you know go to battle and make sure my keywords and all that stuff is good. So yeah, LinkedIn is a great place to connect. Um and, and so those are kind of two of the main channels, one for me personally on LinkedIn and also for the company. At this point of the company I am still on quite a few of our demos so you know you might end up with me or my co-founder, one of our you know leaders on customer success or sales. Um but we like to stay very close to our customers because they're the ones who ultimately inspire you know the next wave of features.

Jake Aaron Villarreal: Great. Tito, thanks so much for joining, really appreciate your time. And uh the listeners for spending your time with us, it means the world to me, really appreciate that uh on this Tuesday, heading into the middle part of the week. Thanks so much. And again my name is Jake Aaron Villarreal, can't wait, wait to catch up with you all in the next episode. Until then, take care.

Before we wrap up, I want to give a big shout out to all the entrepreneurs that have joined to make this podcast possible. And for all the listeners for listening, it means the world to me that you chose to spend your time with us today. I'm your host Jake Aaron Villarreal signing off for now, but can't wait to connect with you all soon on the next episode. Take care.

This show is sponsored by Match Relevant, a company that helps venture-backed startups find the best people in the market. And they do it in three simple steps. First, they sit down with founders to understand their story. Second, they tell their story into multiple candidate channels. And third, they schedule interviews within 48 hours. Find us at matchrelevant.com to learn more about how we do it.

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