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Why This Entrepreneur Who Leads More Than 1,000 Employees Prefers to Eat Lunch Alone We caught up with James Reinhart, the CEO and co-founder of thredUP, to learn his leadership hacks.

By Rose Leadem

Opinions expressed by Entrepreneur contributors are their own.


In this series, Leader Board, we speak with CEOs, managers, founders and others who lead organizations to learn what makes them tick, what they look for in new hires and even where they eat lunch.

If you ever find yourself walking through one of the offices of the secondhand ecommerce site thredUP, you might stumble across some 4-foot-long purple crayons. To an onlooker, they may just look like some quirky decorations, but there's more to them. ThredUP founder and CEO James Reinhart awards these large purple crayons to employees who have done exemplary work.

Related: Why This First-Time Entrepreneur That Built a Website With More Than 5 Million Monthly Visitors Sets Aside Time to Work Out With Her Team

And that's just one of Reinhart's fun leadership hacks. From asking new employees to teach the company about one of their passions to making his employees coffee and cappuccinos in the morning, Reinhart makes sure to cultivate a fun yet focused office culture.

Back in 2008, after having difficulty selling his clothes to a consignment store -- they wouldn't accept every brand in his closet -- Reinhart launched thredUP, one of the largest online thrift stores. Fast-forward almost a decade, thredUP employs more than 1,000 people across the U.S. and has $131 million in funding. In 2017 alone, the company estimates it will sell more than 10 million items.

Of course, running a growing business can be exhausting, especially for a CEO who identifies himself as an introvert. Luckily, Reinhart's time spent running thredUP as well as launching other ventures, including the Pacific Collegiate School and Beacon Education Network, have helped him develop his own set of effective leadership tactics.

We spoke with Reinhart to learn how he successfully runs one of today's largest online second-hand consignment shops.

On the most important leadership traits:

"The number one thing that I focus on is clarity of communication. Leaders need to be able to communicate what they're trying to accomplish, what the strategy is [and] why. I've found that over the years, when I don't communicate effectively, things fall apart. But when leaders communicate effectively to their teams, to their investors, to reporters, they can be really successful."

On leadership style:

"I tend to be somebody who focuses on setting the context of what we're trying to accomplish, hiring the right people and empowering them to make decisions and run with things. I'm not the type of person [who] micro-manages a lot of tasks that I'm looking over people's shoulder. It's really important to give people the freedom and responsibility to perform.

"Ultimately a leader's job is to hold people accountable for doing what they said they were going to do. So [if] they can't deliver or they underperform, my job is to give them feedback so they can get better."

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On habits that help him lead:

"I'm very disciplined about making sure other people's priorities don't jump the list of priorities that I have for myself. Every day I'm very clear about what I need to accomplish, how much time it's going to take [and] what's on my to-do list, and I don't let other people get in the way. I think sometimes you can end up very reactionary in a [leadership] role where you're just putting out fires without being very deliberate about what you need to accomplish. I'm much more deliberate each day [and] each week about what I need to get done and I hold myself accountable to getting those things done."

On challenges:

"The general challenge for me is to be able to give everybody my full and undivided attention given that I have a lot of things to do and they're all very different. It's only mid-day today and I've had 14 meetings -- I've run a company meeting, I've done a whole product review, I've had a one-on-one, I've had coffee with an old friend, I've worked with my assistant on travel. So, in any given day, I have to context-switch very rapidly.

"I'm not a big procrastinator and dweller. I make decisions, I evaluate things and I move on. I believe that CEOs and people in leadership positions need to be able to make good decisions at a high velocity. It's one of my core things: high-velocity decision-making."

On the toughest business decision:

"Back in the early days, thredUP was primarily a peer-to-peer platform like eBay where we connected buyers and sellers. And we switched the business model such that we put ourselves in the middle between buyers and sellers -- so we took on inventory risk, [and] we did things on behalf of both buyers and sellers. That business transition was very difficult because we had investors, customers [and] employees who were all aligned around one strategy. I needed to stand up and convince them that strategy was wrong even though it had been my strategy.

"For me, making the switch and then aligning everybody around the new strategy was really hard because I had just spent the prior two years telling people that the old way we were doing it was the right way. I brought a lot of data and a lot of customer insight to the conversation so it wasn't just me having an opinion. The most important thing was to get people the right information so that they could they can have an opinion."

On the most important traits in a new hire:

"The thing that I look for the most is what kind of learner [a] person is -- how fast they can learn new things and how curious they are. Intellectual curiosity and people who are hungry to learn tend to be great employees, especially for companies in the earlier stages of their life."

On recognizing employees:

"We have five values at thredUP: speak up, think big, be paranoid, influence outcomes and be exceptional. Quarterly, we give out awards to employees for living one of those values. We do a nominating process where we ask employees to nominate other employees who have gone above and beyond. We have a fun event around a happy hour where we acknowledge those people and at the end, I select somebody who wins the big award, we call them up in front of the company and celebrate them.

"We give [them] an OpenTable gift card and a big 4-foot-long purple crayon. The purple crayon comes from a [children's] book called Harold and the Purple Crayon. It's a book we give to every new employee when they start, because Harold, the main character, spends [the] whole time finding his own way; he makes problems and then solves those problems. It's really about creativity and resilience."

Related: Why This 'Ruthlessly Prioritizing' Entrepreneur Says You Should Write Down One Goal Each Day

On team-building:

"I take my executive team -- my seven direct reports -- [on] a quarterly retreat. Maybe we'll go out to dinner, or we live in the Bay Area so we've gone wine tasting one afternoon. We actually have one coming up that's going to be at one of our member's houses, and we'll probably do a barbecue in the afternoon. We try and keep it fresh and changing."

On unique office rituals:

"As the CEO, I'm always trying to make people coffee [or] cappuccino. For about a year, I would hang out in the kitchen on Friday mornings and make people cappuccinos when they came in. I think it's a way of making sure people know that we're all in it together. People have always loved the idea that the CEO makes [them] a cappuccino during the week."

On managing meetings:

"I try [to] make every meeting as short as possible. A lot of people schedule hour-long meetings -- my meetings are half that time. I use Google's Speedy Meeting feature, so an hour-long meeting ends after 50 minutes, a 30-minute meeting ends after 25 minutes. It allows you to transition to the next thing. I am pretty diligent about ensuring that the meetings I attend have clear agendas, notes that go out around, to-dos, [they] stay on-time [and they] end with follow up."

On scheduling:

"I do my best thinking and creativity in the morning. So I try [to] reserve most of my hours from 7 to 10 a.m. on my creative time, and then I do meetings late morning into the afternoon. The stuff that doesn't require my brain to be as sharp, I do late afternoon. For example, if a friend wants to catch up or I'm doing something more social and less on the business, I'll schedule those for mid- to late afternoon."

On office setup:

"We have [an] open office layout -- nobody has offices. We have conference rooms that people use as needed. I sit at a relatively small desk in the middle of the marketing, product and finance teams. For about a year and a half, I actually gave up my desk and sat in the kitchen because I found myself always in meetings and in the conference rooms [so] all I needed was my laptop and my phone."

On lunch:

"I often try [to] eat lunch by myself because it's the only time I have to myself. I'm actually a bit of an introvert and I need some time by myself to gather my thoughts, and so if possible I eat by myself. I'll go out and get myself a salad or a sandwich and I'll just sit and eat it."

On a strong company culture:

"The most important thing is that it's clear what the company's values are and that management and leadership of the company embrace and live those values. Where cultures go awry is when people treat cultures [as] just things written on the wall, but culture is what you do every day and how you behave. At thredUP, we focus on making sure people live and act the culture. Culture is what people do when others aren't looking."

On cultural mistakes:

"The mistakes that we've made have primarily been in how we've communicated culture to new employees as they come on. There was a time when we made the mistake of saying, 'Well, we gave you the handbook, we gave you the culture book, we showed you videos, we gave you funny stories about the culture,' and just expected people to own, live and breathe it the same way we did.

"Culture is all the little things that you do -- [it] is one of the things you have to keep investing in and do day by day. You can't just give people a culture handbook and expect them to fall into line."

On his biggest cultural win:

"We really value learning, education and teaching each other things. One of the unique things that we do is every new employee who comes into the company [has] to spend 15 minutes and teach us something during lunch. Employees gather around and we ask that person to teach us something they're passionate about or that they have unique insight into. People have taught us everything from how to bake bread to how to play pool to what it's like to travel in Norway."

Related: Why the President of TLC Encourages Her Team to Take Big Swings, Even If it Ends in Failure

On his role model:

"I'm really inspired by Jeff Bezos at Amazon. Great companies need to make the lives of their customers easier and Bezos has done that exceptionally well. I'm always inspired by hearing him talk or comment on what Amazon is doing."

On his favorite leadership books:

"The book that I am often referring to other people is called Competing Against Luck by Clay Christensen, a well-known business professor. The book is really powerful for leaders because Christensen makes the point that to be innovative and to serve your customer well, you have to understand what job you're doing for them [and] where you fit in their lives."

On where most leaders go wrong:

"I think most leaders go wrong by not staying connected enough to what they do in the business context and to the customer. It's easy to drink your own Kool-Aid and believe that your decisions are better than they are or that your jokes are funnier, to use the classic example. Leaders need to constantly be in touch with who they're serving. In a business context, it might be a customer. In a political context, it might be constituents. But leaders sometimes forget where they came from, and the best leaders know right where the core genesis of their leadership comes from and that's in the people that they serve."

Rose Leadem is a freelance writer for 

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