Bring Solutions, Not Problems: An Interview with serial entrepreneur, Michael Krasman, CEO and Co-Founder of UrbanBound

Michael Krasman CEO UrbanBound

Michael Krasman, serial entrepreneur, CEO and Founder of UrbanBound, joins The Best Team Wins Podcast for Entrepreneurship Week to discuss people, process, and books.


Connect with Michael on Linkedin and Twitter.

Follow UrbanBound on LinkedinTwitter, and Facebook.

































Adam Robinson: Welcome to this week’s episode of The Best Team Wins podcast where we feature business leaders whose exceptional approach to talent management has led to outsize results. My name is Adam Robinson, and for the next 25 minutes, I’ll be your host as we explore how to build your business through better hiring. Today on the program, I have friend, serial entrepreneur, co-founder and CEO of UrbanBound Michael Krasman. Michael also happens to be one of the co-founders of Hireology, the company where I serve as CEO. Michael, welcome to the program.
Michael Krasman: Thank you very much Adam, happy to be here.
Adam Robinson: Michael lives in Chicago with his family and, fun fact alert, just happens to be one of the best karaoke performers in the state of Illinois, if not the world. You’ve started and grown several businesses and just completed a successful exit with HomeScout Realty to Coldwell Banker. Congratulations.
Michael Krasman: Thank you.
Adam Robinson: Michael’s featured in the book, and we started Hireology together about six years ago. I’m excited to talk with him about entrepreneurship as it’s Entrepreneurship Week this week, something that he and I both care a lot about. Let’s get started, but first, as is the tradition here on The Best Team Wins podcast, we always start off on the right foot. The best news, business or personal, that happened to you in the last seven days. Michael, what is your right foot for last week?
Michael Krasman: For me, that’s an easy one. Every quarter, we celebrate success from the prior quarter by taking, what we call, our champions out to dinner, so it was our big champions dinner for Q3. We go to, usually, a fun place, so we chose, actually, a karaoke inspired Chinese restaurant up in Lincoln Park. We have a good time and get to talk about all the successes we had for the quarter and get focused on the future, so that’s always a good time. That was definitely my right foot for last week.
Adam Robinson: Awesome. You’ve been doing that for a while across different businesses, correct?
Michael Krasman: Correct. Yeah, that’s probably at least a decade long tradition at this point and going. It’s always fun to be able to take a moment to take those that went the extra mile and exceeded their goals and celebrate it.
Adam Robinson: Very cool. Very cool. Let’s dive right in. Let’s talk about some of the companies you started. Going back to the very beginning, you started a business when you were still an undergrad at the University of Michigan with someone the world knows something about, a guy named Jeff Lawson who runs a company called Twilio. Tell us about that.
Michael Krasman: Yeah, sure. When we first got to college, it was really at the beginning of people starting to see high-speed internet proliferating and access was all of a sudden available. They had recently just wired up the dorms at Michigan, for example, so that you could start to connect directly to the internet and start browsing the web. I remember it was literally at the time when Netscape 1.0 was launched. It was still the first version of Yahoo’s website. It was just an exciting time, and I immediately latched onto the idea of how profound the internet was going to be in terms of affecting how everything that we think about is going to get transacted and done and whether that’s in business or just in our personal lives.
I got together with some buddies, Jeff Lawson being one of them, and we wanted to do something. We came up with an idea to disrupt the printed notes business. I don’t if every university of our listeners had this, but at Michigan, for example, there were three different brick and mortar operations that would hire note takers to go to some of the more popular, widely enrolled in classes like Econ 101, etc. and basically buy their notes from them. Then they would reprint them, typically, on a colored paper like blue or red-
Adam Robinson: Dark red?
Michael Krasman: Yeah.
Adam Robinson: Dark red, not that I know. I never did that.
Michael Krasman: Yeah. They did that so that it was impossible for you to photocopy it and give it out to your friends. They would charge students $60, $70 for the semester’s worth of notes for a single class. We decided, “Let’s change that model.” We did the same thing, we hired notetakers, but instead the notetakers would submit the notes through a little access point that we had created. The notes went online for the students to access for free and then we subsidized the cost of the business by selling advertising to local businesses. We guaranteed that when the notes got printed, the ads that they had would get printed with it. When you’re studying late night and you’re getting hungry, you’re going to call up the sandwich shop or you’re going to call up the pizza place, whatever it is, and there’ll be an ad right there for you to maybe use it as a coupon. That was the first foray into the realm of technology entrepreneurship. We raised a bunch of capital, moved out to San Francisco and grew that business, focusing on academic resources for college students ultimately.
Adam Robinson: Pretty cool. Tell us what you’re up to at UrbanBound, business number four or five for you, I think.
Michael Krasman: Yeah. I think number five, yeah. Really, I’ve been fascinated for over a decade now in really looking at the cross-section of technology and human resources. You and I obviously have known each over for a long time and worked together for a number of years now. There’s so much opportunity for businesses to impact the lives of their employees via technology. What we’re doing at UrbanBound is really helping companies who are dealing with an ongoing problem of how they relocate their workforce. When they need someone to be in different location because they’re, let’s say, expanding their operations or they’re hiring new people that are going to be moving for that job. What UrbanBound does is help employers build and administer robust relocation benefits, and provided to the employee through a web solution. The employee can basically go on, understand what benefits they’re receiving and go about coordinating all aspects of their relocation, while the employer’s taking care of most of the costs. That’s, in essence, what we’re doing. We’re taking what has historically been a very offline process, where you would have to go through a larger company that is going to assign you a team of people that essentially goes to work to help do all of what I just described. We’re just taking an online approach to doing that.
Adam Robinson: Your companies that you work with, I presume these are large enterprise type organizations, is that correct?
Michael Krasman: I’d say it’s a little bit of both. We work with larger companies who have this kind of institution-wide problem of lots of volume of relocations happening on a predictable basis, every single year. They’re looking for ways to improve the employee experience while also being mindful of the costs of the relocation. We also work with a lot of companies that are just fast growing. They go from being, maybe, 100 or 200 employees to all of a sudden 300, 400, 500 and up, and they’re starting to realize that they’re relocating a lot more people and they don’t have any programs in place. They don’t have any policies in place. The administration and logistics of those relocations are often being handled by the talent acquisition team, who really should be focusing their time on finding more talent, but they end up getting bogged down in a lot of logistics of helping someone with their relocation.
It just sort of depends, but we find that anytime that there’s a broad need and there’s enough volume of relocations, call it 10 to 20 and up, per year that UrbanBound can come in and be a very, very economical and just better solution for the employees who are relocating.
Adam Robinson: For your customers, the value prop is all about delivering a better employee experience because people that are more engaged, and think more highly of their employer, tend to be better employees. Is that the case?
Michael Krasman: Yeah, I would say a couple things really resonate when we speak to companies, large and small. It’s workforce attraction in the first place, if you’re competing for a specific candidate. Take an industry like technology where you’re hiring a lot of engineers, at the college level someone’s entering the workforce with seven, eight, nine offers. You want to try to differentiate and show that your company really wants that individual and you’re going to take care of them. Offering a relocation benefit can really help ease the transition in that person’s mind, from wherever they live today to where they’re being asked to move, if they were to come work for your company. Workforce attraction is a big one and then, to your point, workforce retention is another one because when a person makes all these decisions and they relocate, if they, frankly, make poor choices as far as where they decide to live. How they end up therefore having to commute to work. They might love the job but they might not be happy with their lifestyle outside of the office. We try to help mitigate the risk that they’re going to make those poor decisions by providing them access to information they wouldn’t otherwise be able to get it, for example where their coworkers are living and things of that nature. To really help make sure that they plant the roots quickly and therefore have a successful re-lo.
Adam Robinson: Let’s jump in a little bit more in the internal workings of UrbanBound, which you started with a business partner, Jeff Ellman, who we’ll also have on the show. You closed your Series B round earlier this year, congratulations.
Michael Krasman: Thank you.
Adam Robinson: And moved into a new office. You’re a huge believer in the impact that culture has, as you’ve just described, on a company’s growth and success. Tell me about UrbanBound’s culture. What role does it play? Describe it to us in tangible terms. What does it feel like to work there?
Michael Krasman: Yeah, absolutely. I think very typical for startups. We have a very strong work hard, play hard mentality here. We’re at that point in our business’s evolution where there’s still so much to be done. We’re always going to be limited in resources compared to very large companies out there, and so we’ve set ambitious goals and we celebrate them when we hit those goals. We just keep the eye on the ball. We have lots of meetings where we’re looking at how we’re doing against our goals. Everyone in the organization knows what’s going on. We have a rhythm to our business. I know something you and I have deployed at our organizations for a long time now is this idea of having an open communication flow between the leadership team and the rest of the organization, so that everyone is in the know and can make smart decisions.
Adam Robinson: Absolutely.
Michael Krasman: That’s one, I guess, thing that we focus on. Also, just really exposing data, and making decisions using data, has been something that we’ve really been a big fan of for a long time. The more people understand the numbers behind what they’re doing, the more they’re able to adjust their own behaviors to produce better results and also identify problems and get ahead of them and often bring forth solutions, versus the age old issue of someone just walking in your office and dumping a problem on your desk. With the right information, with people being armed with that information, they can come and say, “Look. I’m seeing this happen. I think we need to make a slight adjustment to how we either do this process or handle this messaging.” Or whatever it might be. It just helps you move quicker.
Adam Robinson: Yeah. Absolutely. When you’re talking about transparency, do you mean transparency in just how the business is operating or do you take it all the way to the everybody has a number and knows their number type of approach?
Michael Krasman: The latter. People know how their role impacts our business. We look at that information and literally we get together as a company once a week, and we do our data driven huddle, where we look at all the important metrics in the business. How are we doing in each of the respective departments, whether that’s sales, marketing, customer success, product and we’re looking at how we’re doing. We set goals at the beginning of each quarter and people know what we’re trying to accomplish. Then we’re looking at that weekly, how are we doing? If we’re starting to go off the rails in an area, what’s wrong, what can we do to get things back on track, and then people kind of come together and help make that happen.
As I’ve spoken to lots of entrepreneurs over many, many years, some have an instinct to be more secretive, if you will, with the numbers, or secretive with what’s going on in the business, because they want to own the problem. They don’t want to worry the rest of the organization if there’s something that doesn’t look like it’s going well. I have found my personal belief is exactly the opposite of that. A company is made up of a bunch of people that are all trying to do something, and accomplish something, together. It’s a team. It really is a team, and no one person is going to make that company successful. To the extent that you leverage all those minds that you’ve hired to be a part of that organization to help solve problems, I think the better off you are in the long run and I think the faster you are at identifying and solving challenges that arise.
Adam Robinson: That’s fantastic, so everybody’s got a number. I can imagine that that puts some pressure on management to have systems that can actually deliver that kind of data. How do you, for someone listening who’s saying, “That sounds great, but what systems are required?” How did you make that transition? Is this as simple as pulling a report out of your CRM  system, or is it more complicated than that?
Michael Krasman: Yeah. I think you need to take stock of where you are as a company. When we first got things going, we didn’t have sophisticated technology to be able to really do the things that we can do today. You use spreadsheets or you use basic CRM if you’re not ready to invest in the more expensive CRMs that are available on the market. As you evolve, yeah, it does get a little bit easier and, frankly, you’re able to track more and more data and you’re able to look at more and more information on a real time basis. We now leverage data visualization software that actually ties together each of our disparate systems, whether that’s our CRM, our accounting software, our application so we can see the usage from our users and how things are performing that way, things that we do like surveying, etc. We get that data, it all lives in one place and we’re able to really do some interesting stuff with it but we didn’t always have that.
In the early days, we literally were looking at a single spreadsheet and we all were responsible. Each person owned a couple of lines and you were responsible for putting the numbers in there, daily or weekly, depending on what metrics we’re talking about. We used that information to make decisions. It doesn’t have to be the whole kit and caboodle right out of the gate. You can kind of evolve and get to be more sophisticated over time.
Adam Robinson: I got it. Okay. So it is possible, no excuses.
Michael Krasman: It is, absolutely.
Adam Robinson: That’s what you’re saying.
Michael Krasman: Absolutely, it’s possible.
Adam Robinson: Let’s talk about, then, accountability. Everybody’s got a number. Everybody’s invested. Let’s assume people are the right culture fit, so they’ve earned a spot, they’re a fit, they deserve to be there. What happens when they don’t get it done? What’s your company’s approach to accountability and how do you do that in a way that maintains a meritocracy? It sounds like that’s what you’re going for. But also respectful of the reality that sometimes business is cyclical and you can’t control everything.
Michael Krasman: There’s a couple things that come to mind here. First of all, you’re talking a little bit about someone comes in and they’re a good fit and they’re part of the culture. I think, just to stop on that point for one second, that is a process in and of itself. To make sure that you’re identifying individuals whom you believe are going to help your organization move forward, and move forward in a way that aligns with the way you want to see the company continue to evolve. We are very prescriptive on knowing what our core values are and, when we’re going through the interview process, looking for opportunities to identify if this individual we believe exhibits that type of core value.
Once they are there, getting to the bulk of your question, we are always looking at how people are stacking up against those core values. Once a quarter, we do a leadership team offsite, and there’s a section of that offsite which is known as the people analyzer. We take every individual in our organization, including ourselves, and we evaluate how they are doing against our core values, and then how are they doing in their individual role, in terms of do they get it, do they want it and do they have the ability to do the job. That structured approach to looking at each individual in your company is absolutely one of our processes that we leverage to evaluate if someone’s a good fit going forward in the organization. In addition to that, certainly within each person’s role, we’re very, very, very specific as to what you’re supposed to accomplish in whatever period of time. When you’re not meeting your goals, there’s usually going to be a conversation with your manager. In some cases, we’ll have what we call a PIP, or Performance Improvement Plan, where there’s a very specific set of things that you need to do over a specific period of time, in order to be considered a good fit for that particular role.
Adam Robinson: Yep.
Michael Krasman: We look at this, I guess, two different ways, to kind of summarize. We look at things both in terms of how you’re fitting into the organization and whether or not you’re generally what we view as a good fit for that department, that role, and then also in your individual role in the company. How you’re performing in your job and looking at the specific numbers about what you’re supposed to be doing.
Adam Robinson: That’s awesome. Great experience to share with the folks here. I want to talk, switch to a second, about your bookshelf. I know you’re an avid reader, and some of the best books I’ve ever read came from a recommendation that you gave me. What are some books that have greatly influenced you? I guess part two would be what are you reading right now and would you recommend it?
Michael Krasman: Absolutely. Some of the most influential books, for me, if there’s anybody listening that’s a recently new entrepreneur, there’s a book called E-Myth Revisited by Michael Gerber. It’s probably thirty years in print now. It’s just an excellent book to really get yourself in the mindset of what it means to be an entrepreneur and thinking to scale, thinking about your organization as being a lot of different roles that are necessary. Even if at the beginning, you’re the one person doing all of those roles. It’s thinking about how to build the processes that allow your organization to scale. I think that’s a must read for any new entrepreneur.
Also, just in general, a book I always recommend to any new hire that comes and joins our company, because it applies to any department, really to any person in the world. It’s called How to Win Friends and Influence People by Dale Carnegie.
Adam Robinson: Sure, classic.
Michael Krasman: Just a classic book that talks about how to deal with human beings and in a good way. A book that we really have instituted a lot of the concepts from is a book called Traction, written by a gentleman named Gino Wickman. Traction is really helping you, as the entrepreneur, put in place some of those processes that I was describing earlier. Creating a rhythm with your leadership team and with your company, and making sure that you have processes for things like identifying issues in your organization and then solving those issues. Evaluating the team, etc. I think it gives you a lot of useful tools that you can implement, even on your own, without necessarily needing to have an outsider helping with it. You can actually start doing some of the stuff. It’s not just theory, it actually has tools that you can implement immediately.
I think, finally, just given I’ve always been very fascinated by software and its impact on changing almost every aspect of how we go about our daily lives and running our businesses, I love the book The Innovator’s Dilemma by Clayton Christensen. It’s a book that really speaks to how disruptive innovation comes to be in the first place. How an industry is often disrupted. I know it’s a very overused word these days, but this book really defines what it means to disrupt, and where you’ll typically see that happen. What the pattern looks like. Going back and looking at historical evolutions that happened in other industries, like the data industry, for example. I just love that book.
As far as what I’m reading now? I’m reading a couple things right now. I am reading 1776 by David McCullough.
Adam Robinson: Oh, that’s such a good book.
Michael Krasman: Love history.
Adam Robinson: Let me endorse that one, too.
Michael Krasman: Yeah. It’s a pretty heavy read but I’m enjoying that. I’m also reading The Innovator’s Solution, which is actually a follow up book to The Innovator’s Dilemma, also by Clayton Christensen. It’s really more about the how to, in terms of becoming a disruptor. I recently just completed a fictional book, which I don’t read too many of those, but I just picked one up while I was on vacation, called Ready Player One. It was just interesting. It kind of takes place in about 25 years from now, in this dystopian future where the world has kind of gotten a little bit messed up, and everyone’s online living their lives. Their alternate lives.
Adam Robinson: Sounds familiar.
Michael Krasman: Yeah, exactly.
Adam Robinson: Are you sure that was fiction?
Michael Krasman: Right. Yeah, it’s very … There’s some truth to it, probably. Yeah, that’s what I’m up to right now, reading wise.
Adam Robinson: All right, there’s your crash course. You mentioned 1776 is such a great book. You forget that the United States was a startup at one point.
Michael Krasman: Yup.
Adam Robinson: 1776 was the year it launched, and that book will make you feel like whatever’s happening in your company that may be frustrating you is nothing compared to what it took to get wheels up on this great nation. It’s a pretty awesome book, I agree with you.
Michael Krasman: Yeah, it grabbed me right away. It is fascinating. I think David McCullough does such a great job of really telling the narrative through the words of those who were in it at the time, from letters and from notes taken in different meetings that were being held to discuss those topics and so it’s just a really good read.
Adam Robinson: It’s great. All right, wrapping up here with a closing question. If you were to come back on this show a year from now and report on whether or not you accomplished the most important thing on your plate right now, what is that thing?
Michael Krasman: For me, it’s one word. It’s growth. We are in growth mode as a business and so, for me, one year from now, I want to be able to say that we doubled our business from this year. That’s, hands down, my answer.
Adam Robinson: All right, there you go, that’s Michael Krasman, Co-Founder and CEO of UrbanBound. That’s it for this week’s episode of The Best Team Wins podcast. Michael, thanks for being on the show with us today.
Michael Krasman: Thanks for having me, Adam.
Adam Robinson: All right, there you go. We’re featuring business leaders whose exceptional approach to talent management has led to outsize results. This is Adam Robinson, thanks for joining us on The Best Wins podcast, we’ll see you next week.