This interview is episode 3 of The Control Room: Conversations for Growing Companies, an interview series with entrepreneurs and experts.
Subscribe for new interviews, transcripts, show notes and more.
Listen to the interview on Soundcloud or download from iTunes.
Josh Beser: I am here with Basha Rubin. Basha is the co-founder and CEO of Priori Legal. Basha, maybe it makes sense just to start if you want to tell me a little bit about Priori.
Basha Rubin: Absolutely. Priori is a curated legal marketplace that connects SMBs and high growth start-ups with a network of vetted lawyers at competitive rates. So we’re working with businesses from one employee to 2,500 employees across five states – New York, New Jersey, Connecticut, Texas and California.
Josh: Awesome. How did you start it? I guess, how and why did you start Priori? What’s the story behind starting a legal marketplace?
Basha: So when my co-founder Mirra Levitt and I were at Yale Law School together, we were friends and both were noticing a lot of the impediments, and for businesses and individuals, for that matter, to find, hire and work with lawyers in a cost effective and efficient way. And we thought there had to be a technology solution to it. So we started, after law school, Mirra was at a firm and I was working on Priori full-time to start to build a network of vetted lawyers. So we’ve always believed that one of the main values that we can drive is by creating a set of lawyers who meet a very high quality standard so that when a business needs to find legal help, they can rest assured that everyone they’re finding through us is excellent, and then can really focus on finding the best fit for their needs. So we built both the network and a technology solution that just made everything efficient and transparent. So you can put in your request, view different options, extensive profiles on lawyers, transparent pricing information on sort of hourly and fixed bases and then schedule calls and handle all billing and invoicing, just to make the experience simple and user friendly.
Josh: So you started right out of law school?
Basha: I guess, yes.
Josh: What did your friends say when you said you wanted to do a start-up instead of practicing law?
Basha: Everyone thought I was a little crazy, you know. It’s funny. I do feel that everything has kind of come full circle, where a lot of my classmates from law school are now leaving to join or found start-ups. But at the time, it was definitely an unconventional path. And I remember everyone sort of thinking that it was like a cute project that I was doing, while I figured out what I really wanted to do, as opposed to a real business, as in a real commitment. But, you know, I think the moment I remember perception changing was actually when Priori was featured in the New York Times. And all a sudden all these people who’ve been really skeptical and like not, you know, were all of a sudden, you know, realized that I was doing something real and that it might actually be permanent.
Josh: Was that moment validation for you personally? Or did you feel like you had decided or felt like you were on the right path before that, or…?
Basha: You know, I felt really that I was on the right path before that. Obviously when I, you know, when I first started working on this and also progressing along these very prestigious, regimented paths, I had some moments of self-doubt. But once we really started building the lawyer network in earnest and launched to the public, we started… we had so much validation from our users that we were addressing a real problem. And it was incumbent on us to address that problem well.
Josh: So you mentioned that you had moments of self-doubt. I think anybody that works on a start-up feels that way. How did you get through it?
Basha: You know, brute force.
Josh: What do you mean?
Basha: You know what? I’ve always been the kind of person that once I commit to something, I believe in doing it fully and totally. So both just forcing yourself to plow through and also by finding a community of entrepreneurs who are doing something similar. I really… if I have any regret from my early days, it’s that I slid in myself a little too much. And that both for me personally as well as the business, because I think I would have made more connections and figured more things out more. Two heads is better than one or whatever. I think I would have figured more things out, seen and learn from other people’s experiences much better had I immersed myself in a community very early on. But, you know, I am a slow learner, but not that slow. So eventually I figured that out and met a lot of people who were doing something similar and that was incredibly important.
Josh: How did you meet those people? Just generally, this is like the New York tech community or are these were people specifically working on different problems?
Basha: The New York tech community, friends of friends of friends, people that try to sell to me or I try to sell to them and then we became friends anyway. You know, as well as sort of meeting people through all the normal tech community events and female founders events and that sort of thing. But that community I think for almost anyone makes the process both more fun and easier.
Josh: Makes sense. Did you always want to start a company?
Basha: No. I always wanted to do something entrepreneurial. But I never imagined that I would start a company as young as I did.
Josh: Would you still do it now?
Basha: Yah, absolutely. I won’t do anything else. But I guess that’s the other thing, to harken back to your previous question when, how did I get through it, I got through it by imagining the other things that I could do and none of them seemed as awesome.
Josh: What were the other things you were imagining?
Basha: You know, actually practicing law.
Josh: Not that exciting?
Basha: There are some amazing legal jobs and occasionally, as people progress further in their careers, there are some pretty incredible jobs that would have been an alternate path but I can’t imagine anything else for me right now.
Josh: That makes sense. So walk me through it. You have this crazy idea that you’re going to start this company. You go straight out of law school to go start it. There is this period of time that you had some self-doubt but you fought through it with brute force, met a community of entrepreneurs, then you’re featured in the New York Times. Something has to happen to flip that switch. What happened and how did you get from having this idea that you had started on to being substantial enough to end up in the Times?
Basha: You know, when my two co-founders Mirra Levitt and Daniel Fischer joined full-time, everything accelerated at such a rapid clip. And I think really once we had that, we launched and we started getting feedback from users, both on the lawyer side and the client side. That was extremely positive and the business model hadn’t really been seen before around when we launched. There were obviously a couple of other companies that launched sort of in the same general time frame. People were really excited about a new way to do legal services. I think it’s an industry that is very antiquated. Everyone throws that around but is not very technology forward and people were just really excited about new solutions.
Josh: Do you think that’s changed in the last few years? So you started, I’m sorry, three years ago? Is that right?
Josh: So three years, it feels like there’s been more press about the legal industry getting a little bit more tech savvy. Do you feel like you’ve seen that and…?
Basha: There’s definitely a lot more players in the legal start-up space when there were when I first started working on the idea when I didn’t know of anybody. But… and I think it’s changing around the fringes. But the core of the industry is quite entrenched and has not, I think has not really been, for lack of a word, disrupted. I think there are people who are interested in doing things in new and innovative ways and there are more and more tools out there for them to do it. But in general, I think that the core of the industry is still a dinosaur that needs to be disrupted. But I think it’s going to happen.
Josh: What do you think has to change? Is there an event that you see or a series of events that’s going to push things over the edge to maybe modernize the industry a little bit more?
Basha: I think it’s a tipping point and a trend. I think that all data points to clients’ increasing frustration at lawyers’ billing models and management practices. And over the past decade, clients have increasingly, such as during the financial crisis, been pushing back on legal bills, and on the way in which law firms are managed. And I think that trend is just going to continue until it reaches a tipping point. And then we’re going to see a lot of disruption very very quickly.
Josh: That makes sense. So you’ve built a marketplace and marketplaces are I think notoriously hard. You have the chicken and egg, the customers and the supply. What are some of the challenges you faced specifically with that and how have you dealt with them?
Basha: You know, I would say it’s definitely a dialectic process, right? You need to get… we’ve always taken the view that we need these suppliers first. But we always, we try and work in concert with actual demand. So we’ll onboard some suppliers, wait for the demand to meet and keep on going back and forth so it’s relatively matched. But it’s certainly, there are definitely moments, there have been moments in the past two and a half years both ways, you know, where either we have too much supply and they’re frustrated they’re not getting enough business, or we have too much demand and not enough of a certain type of lawyer. It’s just something we are constantly monitoring in a pretty data driven way so we can do our best to stay ahead of that mismatch.
Josh: Is there any advice – not for legal marketplaces specifically, but for people who are dealing with marketplace products that you would have generally for somebody who is either starting one or working on one that’s in the early stages?
Basha: You know, I think the common wisdom is the right one, which is worry about stickiness and disintermediation, and think about sort of every scenario – how you can make your marketplace as sticky as possible. And when disintermediation is going to happen and how you can prevent it.
Josh: The disintermediation, sorry, meaning someone goes off of the marketplace and just goes directly to the…
Basha: Exactly, exactly. It’s a problem that different kinds of marketplaces have in different ways. For example, I don’t think Uber really has a disintermediation problem because you’re not going to meet one driver who can serve your needs as efficiently as all the drivers ever, right? But with a platform like Upwork for example I think they’ve really struggled with disintermediation because you meet one contractor, you liked their services and the contractor wants to take you off the platform because Upwork charges a fee. And so, you know, other than the assurance of having a third party there to mediate disputes, they have to figure out how they’re going to consistently add value so that it’s not more economic for everybody to get off the platform and cut them out, cut out the middle man.
Josh: But even this is a really old example, I’m thinking about like how eBay will have buyer protection. If you do a transaction outside of eBay directly with the seller, then you don’t have protection. That’s how they try to keep you on platform.
Basha: We do the exact same thing. Priori has a $10,000 guarantee and that’s one of the ways in which, you know, one of the reasons that clients continue to want to stay on the platform. If they stop using our billing system they can’t access the guarantee.
Josh: Got it. Got it. That makes sense. So you mention the Times. You’ve also written for Forbes and I think in some pretty high profile media stuff. Do you feel like that has mattered or had an impact for you?
Basha: Oh we joke that every time we do press, no matter what it is, we get hundreds of lawyers. You know, I do think it makes a really big difference in terms of just reputation, being able to go out there and say you’ve been featured in these places I think makes people less skittish about working with a new business. But you know I think press is really worth it depending on the type of company you are and also what you do with it, right? I think that with B2B companies, you get some press, you’re not going to get a hundred new clients tomorrow, but you can keep leveraging that press over a long period of time to build reputation.
Josh: That makes sense. So I’m guessing that the question, how does one get their company in the New York Times, is a relatively difficult one. But how does one write something for Forbes?
Basha: You know, I was… someone had seen my writing and referred me to an editor and they have a community of contributors and I was invited to participate which was a fantastic opportunity.
Josh: Cool, cool. Okay. So you’ve talked a lot about the company. Personally, what’s your biggest surprise that you’ve had since you founded Priori? What’s the thing that you didn’t expect to happen that has happened?
Basha: Oh this is a silly thing and one that anyone who had worked for longer than I did before starting a company probably would have known, but a lot of my days now are spent with management and HR questions rather than actually digging into to substance of the work, right? It’s about strategy and managing, which for a control freak like me can be a little challenging.
Josh: You mention being a control freak. At some point you have to start delegating stuff. Has that been tough?
Basha: Yah, it’s definitely been something, a challenge for me, but I found, you know, it’s really about building a right team. And as soon as we had, we have an amazing team in place now, just really across the board extremely strong. I couldn’t be happier. And once you have good people and you see what they can do, it gets a little bit easier. I think at first you’re hiring your first person, the anxiety can be more.
Josh: Do you have any examples? Was there something that somebody on your team did that you said, okay, now I can turn something over to them? Like now, I trust them enough to just run with it.
Basha: You know, I think it’s just about… I can’t think of anything off the top of my head. But it’s about, just like producing really high quality work over a long period of time, and seeing that they can do it without me being involved and seeing that sometimes they do an even better job because I have my fingers in a thousand pots, and they can focus fully on one and actually do a much better job than I can.
Josh: Makes sense. Okay, so we were talking earlier before we went on about FlexCounsel a little bit and I am going to admit that I received an email from you guys today about FlexCounsel. And I don’t really know what it is. I’m going to let you tell me what it is. Tell me all about it.
Basha: FlexCounsel is a new monthly subscription offering that Priori launched just today. We’re launching in beta right now. And the need that we saw was clients… there’s certainly a need for recurring monthly packages, and that’s something that a lot of different law firms and a lot of different companies have done, right? You know, you pay $1,000 a month, you get X amount of legal, blah, blah, blah. So what we’ve been seeing is clients who were using multiple lawyers in our platform every single month, and we wanted to create a subscription offering that enabled them to do that, and so we can really be a clearinghouse. So you get pretty deep discounts on packages of ours that you can use across different lawyers in our network. So if you have an 8-hour package, you can use 5 on a corporate lawyer, 1 on tax, 1 on employment and 1 on IP at an extremely low rate for the subscription. So you’re paying the equivalent of somewhere between $130 and $150 an hour for lawyers who typically through the network are charging usually north of $300.
Josh: So why would the lawyer sign up for it?
Basha: For a lot of lawyers, regularity matters. They want to lock in clients who are using them every month. They have predictable income. And they want clients to get comfortable with them and use them as their outside counsel. So they’ll use them even more when a larger need arises.
Josh: That makes sense. I guess a lot the solos and small firms folks that I’ve met, having regular hours is probably one of the biggest issues, right? You need to know that you have a base. So that’s interesting. And then, just walk me through that relationship a little bit more. So you pay for a flat rate number of hours a month and then is there any involvement with Priori in selecting the lawyers or doing any quality control or anything? Or is it essentially, you’re matching with them and the GC or the company is managing the direct relationship with the lawyer after the match is made.
Basha: Well, to begin with, every lawyer in the Priori network is pre-vetted, so you are at first working from the sort of very elite pool of lawyers. We were extremely rigorous about our admissions process, more so than anyone else out there. And from that, we feel confident that all of the lawyers in our network will be fantastic. But beyond that, we really, the lawyers who sign up for FlexCounsel are ones who are really excited about the model. We don’t want someone participating in this who doesn’t understand the value to their practice. So these are lawyers who are all excited about providing services in this way. And then we hand select lawyers, like we do for any matter, for your FlexCounsel request based on your need. So you can add as many members to your legal team as you need and then leverage that on ongoing basis. And of course all the billing and invoicing happens through Priori as well, just to keep things simple and streamlined.
Josh: So you launched on beta today. That’s exciting. That sounds very interesting. So a couple of other things I want to ask you and I’ll let you go, because I know we’ve got a time thing. First is… I mean a time thing because we’ve talked for 20 minutes. I always like to ask who you think is at the top of your field or someone that you look up to. Not just necessarily like a super famous person but somebody who’s doing something at least in the same universe that you’re working in and you think is just doing an awesome job in it.
Basha: You know, I always thought picking specific people, but one of the companies that we really admire is GLG in sort of creating an expert high quality network.
Josh: Why? What is it about them that’s interesting?
Basha: I think they have been able to scale quality expertise in a way that I’ve seen very few other companies have been able to do.
Josh: Okay. Well, and then the other thing that I’ll just like to know is that is there anything that you’re listening to or reading right now that you think people should know about. Podcasts or books or articles or anything that you’ve read recently.
Basha: Does it have to be about business? I’m really bad at reading about business, but I do read a lot.
Josh: No. Whatever you like.
Basha: I’m super into The Last Kingdom. I don’t know if you’ve heard of it.
Josh: Tell me about it.
Basha: It’s a BBC America series that… the series is good but the books are excellent. It’s about the Viking invasion of England in the 800s but it’s spectacular. I read 5 books over Christmas. And then I read the John Overing books, the new John Overing book, which was okay. And then I read a book called Among the 10,000 Things, which was also okay. But The Last Kingdom.
Josh: The Last Kingdom is the one that…
Basha: You got to check it out.
Josh: Nice. Okay, cool. Cool. Anything else you want to add before we go?
Basha: No I think that’s it. This was a lot of fun. Thank you for inviting me to participate.
Josh: Sure. Thanks for joining me. Alright, Basha. Take care.
Basha: Okay. Bye.
This interview is episode 2 of The Control Room: Conversations for Growing Companies, an interview series with entrepreneurs and experts.
Subscribe for new interviews, transcripts, show notes and more.
Listen to the interview on Soundcloud or download from iTunes.
Here's the transcript:
Josh: Yes, I’m here with Ben Alden. Ben does BD and Legal at Betterment. Ben, thanks for joining me. How are you?
Ben Alden: Great, great, thanks for having me. Looking forward to this.
Josh: Awesome. So for people who don’t know, do you want to give me a minute on what Betterment is, and just a little bit of background there?
Ben: Sure. Betterment is a start-up that wants to give the answer to the question, what should you do to manage your money? Today, you come to us, we ask you questions about your financial goals, and then we automatically build, customize and manage investment portfolios for you. We provide investment advice around retirement too, so you can come and get all those tricky questions that no one will answer for you answered automatically and for a low cost.
Josh: And so you do both business development and legal there. What for you and for you at Betterment, what does BD mean? What does that mean for you?
Ben: That’s a good question. So right now, really, a lot of business development for us is discovering whether or not we should be doing greater development or other sales efforts in certain particular and targeted areas. You can imagine that… not always clear what BD means. I think BD means something different in every single start-up and we kind of started with that in mind. Okay, so what is this? An answer is, let’s explore inbound and outbound opportunities to see if there is anything that makes sense in terms of partnerships, new lines of business, moving international, etc. Where should we spend our time? And then once we do that we act accordingly.
Josh: Okay, okay. So you’re in basically the scouting area to try to figure out if something makes sense, and then if something does make sense then you hand it over to another team that is going to work to implement there?
Ben: Absolutely, or build the team as it might be if it’s brand new. But obviously very sensitive about, making sure that we aren’t aimlessly thrashing. The best thing to do in our view is to have clear focused targets and to go after them. So right now until you have those targets you’re exploring.
Josh: That makes sense. And so I want to get into how you get to do BD as a lawyer because I think for a lot of lawyers that is kind of a dream job or a dream part of a job. But maybe let’s back up a little bit. Talk me through the story of how you ended up at Betterment to start with.
Ben: It’s… the way I think it happens with a lot of start-ups for lawyers, and that’s, I knew someone. So I was a consultant before I went to law school. And our CEO and Chief Product Officer both worked at the same firm at the same time. And I didn’t know John as well. But Anthony, Chief Product Officer, basically trained me. He took me as a wet behind the ears consultant and he taught me all that he knew. I loved working with him. I thought he was absolutely wonderful. Always stayed in touch with him because of it. And years later, maybe around 7, 8 years down the road, I came to him during one of our normal lunches and said, Anthony, I’m thinking about a start-up thing. You’ve been in Betterment three years now, what’s the story? And he said, I think I have a job for you. So I got a little bit lucky there.
Josh: Wow. So you were like one for one there.
Ben: Yah, I was very lucky there although I’m hopeful that really working for Anthony as a consultant was the longest job interview I’ve personally had.
Josh: Makes sense. So in some ways it sounds like that story is… you could say as a cynic that that’s impossible to replicate, right? Like, oh he knew someone. But it sounds to me like that’s something that anyone who wants to do this could replicate. They might not do it at Betterment, but the idea… meaning in working with someone for a long period of time, building that relationship and then it ultimately turning into something that’s a job, whether it’s with that person’s company or someone that they introduced them to. That feels like great advice, and something that people could try to do long term.
Ben: Absolutely. And that’s really my advice when people ask me, how do I get into start-ups? You can get these great start-up legal jobs and they tend to be a lot fun, I personally think, by applying. But then once a great company like Canary or Betterment opens up a job for a lawyer, they’ll get 300-400 applications, so it’s not that you can’t get a job that way, it’s just not the easiest. And because culture’s so important at start-ups, knowing people at these places matters a great deal.
Josh: Are there any steps you would take or you would advice someone else to take if they are like sitting in a law firm right now or even in an in-house job in a big company, or even a non-lawyer in a similar situation who’s in big consulting firm or a big company and thinking, hey I want to do something in start-ups. Where would you tell them to start?
Ben: Start with your network, I think. A lot of what I was trying to do at first I got very lucky with Betterment and knowing Anthony. But when I first started kind of trying to figure out what to do, the best advice I got is, always be having coffee. Meet people, try and learn about what they do. A meeting is not like a coffee, as in a promise of anything. But the more you get to know people the more you understand what you like and what you want, and then the more targeted your search can become. I would also encourage lawyers to the extent you are interested to work in a start-up or company to learn a lot about it before talking with people. I think that is good advice for most interviews but people with start-ups, at least in my experience, love when you know about what they do and you have a real passion for the business, because that’s what will keep you here late at night when you are not getting paid like you are as a lawyer. And when no one is telling you to stay there.
Josh: When you say that, to learn as much as you can, you give people a couple of places you would look, I mean, you know, AngelList or where else would you focus your attention?
Ben: Sure. Great question. One of the best pieces of advice I got was obviously beyond your network and anyone you know is to look at really great venture capitalists in your region, or who invest in your region. Like New York, San Francisco, LA, Chicago, wherever. And then look at their portfolio companies. It’s a great way to learn a little bit about what’s out there, what are people hearing and seeing, what investments companies are getting and in what areas, whether that’s in tech or certain consumer type of stuff. You can get a sense of it by looking at these pages. And oftentimes some of the sites even will have open positions posted for all their portfolio companies.
Josh: That’s actually really good advice and here in New York we’re lucky to have a lot of very active funds and that portfolio information is very accessible. And you can start to see, I think if you spend a little bit of time getting into Crunchbase, you can see where the overlaps are, who’s investing together and seeing patterns in those sorts of things if it’s something you really want to dive into also. You mention this idea of always having coffee. I’m not sure if you know this but one of the things that I spent a lot of time on in the last few years is both writing about and helping people who are unfamiliar with start-up culture understand what that means and why it can be beneficial to you even if you’re a lawyer in a big law firm. And that really started for me and describing it to friends who are in big firms and wanting to stay there, hoping that they might understand this idea that it’s a very easy and low friction thing you can do to ask somebody to go spend 20 or 30 minutes together, and frankly look for ways you can help them and learn from them in the process. That’s something that I’m super familiar with and frankly had a lot to do with my ending up at Canary five or six years after I started thinking about really getting into start-ups. For you, you talked about your relationship with Betterment, but can you talk about any other ways that you used or you’ve seen other people use coffee meetings as a great way to learn?
Ben: Sure, sure. One of the best things to do is kind of over the course of the coffee if you really click with someone, try and build that relationship. I’ve really learned an unbelievable amount from people who I consider mentors, maybe the first time you have a coffee and you have five coffees, you really click with someone, two, one, two, three, four, whatever it is, percent of the time or number of times. But then following up and trying to be helpful to the person but also building that relationship because it’s maybe not the first coffee, it’s the second or the third where you start to learn a lot more. I think both about what it’s like to work at a start-up, but then also, get closer to getting more help and advice. It’s not always possible tol do that, but it’s… oftentimes people have me out for coffee and they’ll say, great, Ben, tell me about Betterment. And my first instinct is, it would have been great if you told me you really liked Betterment. You don’t have to do that but that’s okay. If you’re looking for a job here, the first answer is I hope you care. But if you’re not looking at Betterment that’s also totally fine. And having me tell you about start-ups is great, and the way most of these calls end is, great, thanks Ben, great coffee, really enjoyed meeting you. Let me know if someone’s looking for a job. Thanks, bye. And that could be the last time you hear from that person ever.
Josh: How does that make you feel when that happens?
Ben: At some point you get used to it. It’s not like a bad emotional feeling. It’s just, well, how am I expected to kind of keep you in mind if I… I do keep people in mind who I know and who I kind of have relationships with and who I think would be great because there’s nothing better than placing someone in a company and having everyone really succeed. The company, the person, I like making those connections but it’s hard to do that if I’ve had coffee with you once a year and a half ago. I can barely keep what I had for breakfast in mind some days, hard enough keeping someone you haven’t really kept in touch with.
Josh: I struggle with the same thing. And one of the things people ask me, well, what can I do? What can I even… I don’t have anything to give. I don’t know what to tell him. And one piece of advice that I try to give people is like if you have nothing else to say, I might spend half an hour or an hour with you at a point one month ago, just send me a quick note to say, hey, I really appreciate you spending the time with me, I appreciate your advice on this or your recommendation for this. One thing we talk about and show that you did something about it. Or that you internalized it and something happened. That for me is an indication that you’re trying and you’re interested and that there is some value in the discussion that we had. And for me it’s actually like, it kind of depends on the level people are in their career, but for somebody who’s just out of school, somebody keeping me posted on what they’re doing actually really… I feel like there’s value in that for me and I’m glad that they do it.
Ben: I think that’s awesome. I agree and it’s great and I wish more would. I actually sometimes would explicitly tell lawyers, I really do like… I’m telling you to contact me, stay in touch. You probably won’t because that’s not lawyers think much about. We went to school and schools are like great, you’ll succeed by getting good grades. Okay, so you kind of put your head down and you work and then you settle off and you’ll succeed by XYZ and you kind of do that for a few years and you get to some point in your career where you realize it’s actually relationships you build, the people you know. It’s the people you pick up the phone and call and say, I have a legal question, do you know anything about this? Or especially for career stuff and that doesn’t really come through in our legal training or cultural super much until people get a little bit more senior. But I do try and encourage people, and I do chat with them younger to remember like this is a relationship, it’s a real living, breathing thing. You can’t say we have a relationship or I met this guy once for coffee, he’s taking care of me from now on.
Josh: Right, right.
Ben: It’s like business school a little bit.
Josh: Yah, right? Because it’s kind of a natural thing in business school. It’s part of the core skill set that you learn is that you need to build relationships with people and ideas. I don’t even really like to think about networking. It’s just essentially, you need to know people who are doing things in your industry and the industry you want to work in. You need to know as much as you can. This is a method of information gathering and building relationships and trying to be helpful. And like, you’re right. Not only is it not part of our core curriculum, but if you end up going out of law school into big law, then to the extent that you’re ever really thinking about that sort of thing, you’re thinking about it from a client development perspective. And then you can end up in this really toxic, like, everybody I talk to I have to pitch, mentality. And that’s, I’m sure, I feel as an in-house lawyer, I’m sure you do too, that’s the last thing you want to be doing. Because you think you’re trying to have a conversation with somebody, and then you end up with a sales pitch.
Ben: It’s the worst. I had someone once who’s on like a sales or some lawyer was trying to sell some business, and he’s like, you know, pretend I’m your uncle, I’m going to give you some really good advice, right here. And my first thought was, oh god, that’s not really what I want to hear. That’s like the last thing I want to hear. But, yah…
Josh: Yah, it’s crazy. It’s crazy. So, you’ve been at Betterment for almost two years, is that right?
Ben: That’s right.
Josh: So you guys have grown a lot. I told you when we met, I’m a client and I know that you have rolled out a lot of new products and new initiatives. The company’s growing pretty quickly. I guess I have really two questions around growth. One is, how do you keep your head on straight and keep your priorities and the work that you do in the right order or in the right at least levels of things that you should be spending your time on. And the second piece of that is whether you have anything that you have done that you could give as advice to other people who are in companies that are growing like yours or mine to help them through with the same type of challenge.
Ben: Sure. So how do I keep my head on straight is a very good question. I think most days I do. Some days you don’t because you’re just so busy. But always staying as organized as possible and trying to build out systems and processes for handling standard and repeatable legal tasks would be the first place I would start. Again, it’s in-house, you see it very quickly and at a law firm you don’t. And that’s just building efficiencies. I was a litigator by trade and every time you got a brief, you basically write everything from scratch. You wouldn’t… there is always a brief bank somewhere where you might be able to find like similar types of briefs, but people typically didn’t use it. And as a result, you end up doing lots of work over again. At a law firm, if you have to negotiate commercial contracts a lot, you don’t want to have to rethink each one from scratch, so how do you create a process both for in-taking those contracts but then also how do you come up with a process for reviewing them and in a systematic, repeatable and transparent way. That can be a checklist, that can be best practices, it can be a spreadsheet. But these are the types of things that are important to think about, otherwise you’ll find yourself underwater quickly and not being a great business partner to the rest of the organization. That’s one example. And I think the other is making sure you scale appropriately. I do happen to b elieve that your legal department can be truly value add, especially in a fast growing company, where if you’re not careful, things will break. We happen to be in a highly regulated industry, so the lawyers are a bit more involved in both the regulatory issues but also with the product. We want to build in a systemic, smart way, so how do we as lawyers have a good product sense while helping to achieve our business goals. So all these things are kind of organization but then also remembering that you can find the ways to add value, I think are pretty important. And I confess I sort of forgot the second question.
Josh: Oh and then to what extent are the things that you’re doing and that you’ve done, is there advice that you would take out of that, you would give to other people, to somebody who’s just starting at a company that looks like yours, maybe whether or not heavily regulated. But in a fast growing start-up, in a role that they’re going to have to take on a lot quickly, and things are moving around a lot, what would you tell them?
Ben: The single most important thing for anyone at a company that’s smaller and growing, hopefully growing fast, is to have a sense of ownership over your work and your problems. And for lawyers on some level hopefully do you really get good training, especially at a law firm for this, and after that sense of something doesn’t feel right here, what’s the issue? But then following that up, tracking it down, not letting it go until it sits. That sense of ownership I think allows you to really move into a lot of different areas and really prove your value at a company and allows you to do non-legal things too. One of the reasons, I think you asked this in the beginning. I think I got into moving into business development and operations too is because I was helping someone with something very early on and at the end of the call, I memorialized it, created a follow-up plan, and basically said, I think this is what we should do for the next two, three steps with this type of relationship. And I think the person is my boss at the time, like, oh, wow, okay. That’s really helpful, thank you. And so I just started doing it, I started doing the job. And the more I did, the more responsibility I would take on over there too. There’s all sorts of opportunities and now I’m off the original point, but really what I’m saying, you exercise ownership and you show yourself willingness to do work and to do it well. At a start-up you’ll have all the opportunity in the world to grow.
Josh: I think that’s really interesting. It’s something that I’ve seen and I came from about a 10,000 person company before I joined Canary and it’s a huge difference in environment. But one of the things that I’ve seen here is that the company has grown so quickly that there are not yet people who own not just like particular tasks, but groups of tasks, like groups of responsibilities that you would see in a larger company that like if somebody’s been doing that job for however many years, we just haven’t really needed it yet. Or when we’ve needed it it’s kind of been addressed in an ad hoc way just to kind of get it done. And there are a bunch of places, mostly in the operations area here where I just kind of grabbed a whole bunch of these things and then you just start doing it and then hey guess what, now the CEO says, oh, well now you own this. So okay. Fine. That’s fine. But you’re right. You start really getting into non-legal stuff really quickly and I don’t know, for me that’s exciting too. Not because I don’t want to b e a lawyer but because it’s great to understand all of the things that are going on inside of the company. It helps you not just be a better lawyer but it helps you to be a better business person too. I’ve seen that.
Ben: And I always find one of the things that’s really fun about being a lawyer at a small fast growing company is that if you get work and people like you and trust you, you’ll eventually know more about the business than almost anyone, because you sit across and interact with almost the entire organization. I gave a presentation to the company once just about legal department stuff and I put up a chart of all the faces of the people in the company with a little start next to people me and my team had spoken with in the last week or worked with, and almost everyone was on there in some form or some way. Not everything is a big meaty legal issue, sometimes it’s just a simple thing like a touch base or someone had a question about something. And so you get a good sense of what’s happening, when it’s happening and how it’s happening. And that’s really cool. I really like that part that if you’re just a senior marketing director at the company, you might not have as much of a sense across all pieces.
Josh: Yah it’s definitely evident here too, where you realize you do touch every part of the company. Every decision that’s being made, you can have some influence, but you at least have some visibility into it, and that’s really cool. Okay, so to take just another couple of minutes if you don’t mind, I just wanted to know if there’s anything you’re either reading or listening to which you’re really into right now. I like to ask that. Reading, whether it’s business related or not. Listening to podcast or music or anything that someone could hear and say, wow, I want to check that out.
Ben: If that’s the case then I’d definitely say the River by Bruce Springsteen. The Boss has just put out a box set and I’ve been listening to that album non-stop. Not strictly legal but a great moment in Americana for everyone out there. One thing I love doing is trying to consume as much stuff as possible. It’s unbelievable what’s free and on the Internet about all of our businesses and just even being an in-house lawyer and how to grow and run things. So I actually spend a large amount of time fracking through those types of documents. Someone will sent me a treatise on something, some counsel will say, hey, look, this is how a transaction works or read some new IP development. I really enjoy all those areas of kind of following up on that stuff. It’s… I don’t know if you remember studying for your bar or not, the world’s most fun thing on earth. But there was a moment at least for me and I think for some other people too where right before you take the exam, the hard work is behind you, when you say, wow. I know a lot about a lot of random legal stuff. And that moment, you’re like, I could probably be a useful lawyer to someone. If my mom has a question, I might be able to answer it.
Josh: Right, and it’s the last time in your life you’re going to know the answers to a lot different questions.
Ben: Yah, without a doubt. And I kind of like that feeling in-house. It’s… Look, having a sense of what you don’t know is as much if not more important about what you do know. But I do like that broad sense of all these different areas. So I do a lot of random reading from that perspective. PLC puts out good stuff. Some of the start-up lawyers put out some interesting stuff. And yah…
Josh: Awesome. That’s good stuff. Right on. Okay, well thanks for joining me. Anything else you want to add? Can people find you on the Internet? Are you on Twitter or anything?
Ben: I wish I was on Twitter. It’s probably better that I’m not. You can find me at email@example.com, or on LinkedIn. And I’m always happy to chat with people. I think when I went through the process, Anthony made it easy but I talk to a lot of lawyers who are unbelievably helpful and always happy to pay that forward a little bit.
Josh: Cool. Alright, Ben. Thanks for joining me.
Josh: Right, bye bye.
This interview is episode 1 of The Control Room: Conversations for Growing Companies, an interview series with entrepreneurs and experts.
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Here's the transcript:
Michael Baldwin: Well, it’s funny. The interesting thing and fortuitous thing for my work is, you can argue that I’ve done this work for 35 years because I was doing it the entire time I was in advertising. And then in earnest, in the last 8 years, doing it for real for my consulting practice. But what’s come up, so I’m always calibrating, and what’s sort of come up recently as a sort of overall, universal issue is, I don’t know where to begin. That’s one huge one. I don’t know where to start. I just got tapped to speak at CES for half an hour on XYZ, I don’t really know where to begin. I just know I’m nervous about it and I’m worried about what to do. So that’s a huge one. The other gigantic common denominator around the world which is see all the time is people don’t know that a slide is basically a billboard in disguise, and when…
Josh: What do you mean by that?
Michael: Meaning you should be able to read the entire content, to absorb the entire content of any slide whether it’s imagery or words or whatever it is, in under 10 seconds. In under, probably, 5 seconds because if you imagine you’re driving on a freeway and you go by a billboard, you don’t see if for very long, but the ones that are done right, you get it immediately, because it’s consumable at 55 miles an hour in 5 seconds. So people don’t understand that they need to reimagine how they think about slides. Currently, most people think about slides as a repository for as much information as you can fit on the screen. Most common problem.
Josh: And when you think about that, sometimes isn’t that cultural within a company? Like everybody does their slides the same way so what do you say to somebody that you’re saying, no, that needs to look like a billboard? And they’ll say, but nobody in my company does this. So you’re asking them to take a huge risk. What do you say?
Michael: Well, the thing is, and that’s a lot of companies I work with have that problem. And if you consider the fact that since Microsoft bought PowerPoint, which is probably the most prevalent presentation software out there, you know, Apple’s version is called Keynote, since that day 30 years ago, it’s just gotten steadily worse. It’s just gone downhill on a regular basis. So in other words it’s taken a long time for it to get as bad as it is today. So reversing that trend is not going to be overnight. And it has to sort of gradually get the buy in of people in companies where they’re hide bound doing it the way that’s just actually a complete, communications-wise, waste of time. So if you show them how much more effective it is, how much more fun it is to work with slides that are designed the right way, then it’s a sort of process by exposing more and more people and then over time, getting companies to change the paradigm for them in terms of what decks are meant to look like.
Josh: That makes sense. And I’ve definitely seen the impact of that in doing it myself. To take 90% of the words off of a slide. That’s very interesting. So you mentioned your ad background and transitioning into a consulting practice. At what point did you decide you wanted to do this full-time and what’s the story behind that?
Michael: It was December 5th, 2010, and something just hit me and I realized it was time. Attitudinally, I’m geared to be a, what they call, subjective personality which is owning your own business. So I don’t know, something just snapped, switched one off and I decided, okay, I’m now ready to do this. And that was what, going into my sixth year now.
Josh: Yah, yah. When you decided to do it were you confident that you were going to succeed at that point?
Michael: Not at all. Are you kidding? No, not at all. And I think there’s something I can’t… people refer to it as a Mandela, that circular diagram. You start out ignorant, then you get arrogant, and then you get stupid, and then you make mistakes, and then you’re back to ignorant again. I think the process is being totally intimidated by the idea of leaving a corporate environment where the mothership takes care of everything, pretty much, and going out on your own. Because the other thing is when you do it, you’re the accountant, you’re the account person, you’re the presenter, you’re the owner, you’re the client-facing sales department, you’re everything. So I think you have to build up enough courage to get to the point where you hit the Malcolm Gladwell tipping point and you say, okay now I think I can do this. And then it becomes, you make at least a short term commitment and you see how it goes. And then the whole thing is about getting your first client.
Josh: So you mention making a short-term commitment to see how it goes. Did you treat it as an experiment?
Josh: Did you think, I’ll do this for some period of time and see what happens, or…?
Michael: I think that’s sort of inevitability, because if it doesn’t work, you got to rethink it. And also, you have to account for something that is unaccountable for, which is the learning curve, because you’ve never done it before. So I didn’t know quick books, I didn’t know a lot of stuff, even though I’d been in the business world my whole career. And you learn about taxes and taxation and how you do it and the fact that when you create a corporation versus an LLC. So you get an education that starts almost immediately, you start learning stuff.
Josh: That’s really interesting. Aside from the sort of administrative stuff or the nitty gritty of running a company, what was something that was unexpected for you about doing this on your own?
Michael: Let’s see. I would say how long it takes to get a client. Because in the work that I do it’s very, well, it’s expensive, number one, and it’s very intimate because I work with a lot of CEOs, so there is the ego management there. And you have to get over the hurdle of them thinking they know… actually, the good ones always want to get better. But word of mouth is a lot of how it works, and that’s actually a good thing because outside of that, in my category, in this particular one of speaking, there’s a lot of competition but there’s no one who does what I do the way I do it. But nevertheless, until those people are aware of the differentiation, they don’t know me. They don’t know what I offer and why it’s good and why it’s different and how it works. I’ve got clients - Ogilvy, I’ve worked Ogilvy for 7 years. Overly, it’s been over a year to get my first two half-day pilot.
Josh: Wow, wow. And going into that kind of a situation, you probably know a lot of the people already, you’ve had that relationship with these people for a really long time, right?
Michael: Yah, yah. The CEO of Ogilvy & Mather New York, I have known since 1994.
Josh: And it still takes over a year to get in.
Michael: Yah, yah.
Josh: Wow, that’s incredible.
Michael: It’s because of the matrix and budgets and timing and all kinds of stuff like that.
Josh: You think there’s a lesson there for people who are trying to work with big companies generally, about getting clients and what that process looks like?
Michael: I would say the lesson is patience and diligence. And keeping in mind that if you get a client like a big global client, Ogilvy is a global business, they have offices all over the world. Because I also have my book which just got published. So often with my clients, I want the book to be hand in hand with me, in other words, making it a textbook so clients buy 5,000 copies each. And I would say, the patience is warranted or justified if you keep in mind the fact that once you’re in the door, and the relationship goes well, you continue collaboratively to expand your footprint within the company.
Josh: That’s great. That’s great. And the patience thing and just working, having worked in big companies and seeing the pace at which things move versus the pace at which things move at a start-up and understanding from the start-up’s perspective that things will feel like they’re taking literally forever, and it’s just because that’s how long it takes sometimes. In large companies, there’s a lot of things that need to happen to work with someone new. You mentioned the book, Just Add Water. Tell me about how you decided to write the book and what you’re trying to accomplish.
Michael: The book came about after I was doing this for 8 years. I realized that, I’m always aware that how bad the state of affairs is in terms of presenting. The statistic is that 30 million presentations take place every day and 95% of them are terrible. So I realized that I wasn’t going to that make much of a dent in the universe by just doing 7 people a day. So I decided if I bottled the day program, which is phenomenally successful, has been since day one, and again, like I said earlier, I’m always, always calibrating a 185 slide teaching deck, to remove what I refer to as any cognitive friction so that it just gets better and better and better and more and more and more immediate, so no one, no major concept is lost on anyone and is absorbed the most immediately as possible. So I just decided that if I just bottled the day program into a book, everyone could benefit from it. So that’s why I did it. And it’s 120 pages. It’s incredibly visual. It’s not like anything in the category. It’s more like a children’s book for adults. And it’s the distillation of the day program, meaning there’s nothing hypothetical or theoretical about it. It’s literally a distillation of something that works incredibly well.
Josh: And it is beautiful. You mentioned that it’s visual. I think that’s an understatement. It’s a really, really pretty book that I think helps when you’re talking about telling stories visually and telling them in a way that sticks with people. That’s something that has stuck with me. And the book is on my desk in my office and I refer to it a lot. I think it accomplished what you’re looking for there. It is really nicely done.
Michael: Thank you.
Josh: So you… let’s see, you mentioned branding a little bit. You’re working with companies, with start-ups, to do branding. Are you working with individuals to do, I guess, I don’t even like saying personal branding, that sort of stuff as well?
Michael: Personal branding. Yah, yah, yah. Absolutely, absolutely. I’ve done a lot of both. I’ve done a
lot of both. And the last two, the two start-ups I’ve worked with most recently, I’m an equity owner in both of them. And that was a branding process from scratch. So name of the company, the website design, the structure of the website, how anything related to the outside world is expressed. Both of them have creative directors who produce stuff. One is a real estate start-up in New York and one is a software designer web designer start-up. So I’ve done it with them. I’ve had very senior people, Fortune 50 companies, in what, for lack of a better word, or words, it’s been all about personal branding, which is like being victimized or in charge of your own, how you’re perceived. So I’ve done both. Love it. Love doing it.
Josh: Yah, yah. And we met through your work with start-ups. Why specifically do you work with start-ups?
Michael: I would say that for me it’s a really funny combination because in both cases, they’re under 30, all of them, and they can do what they do brilliantly. They can’t possibly do what I do for them and are so grateful, completely, totally grateful. Because they just don’t… it’s not their wheelhouse at all. So it’s this funny combination of under-30-year-olds and myself, who’s over 30, and have had a career’s worth of experience, and it’s this amazing symbiosis that takes place. It’s a really great combination. I think it’s not unlike situations where founders of start-ups end up being ejected from the company because they’re just so inexperienced. In this scenario, they all stay, but I get to come in to do what I do for them which they can’t do themselves. So it’s a combination that works so well.
Josh: That’s really, really cool.
Michael: Yah. And also it’s fun.
Josh: Yah, absolutely, absolutely. It’s great that you can do that. And I’m sure it’s definitely appreciated in the way that you said, that you’re bringing something to the table that they just couldn’t have possibly done on their own. Nice to be able to bring that. Let’s see. Anything else you want to cover while we’re together? Anything else you want to…
Michael: Remind me, Josh. The audience is...?
Josh: The audience here? Yah, the audience is people who work for early to mid-stage growing companies, who want to learn things that can help them be better at what they do as they grow their companies.
Michael: Okay, so these people are contemplating doing something on their own, or are doing something on their own, start-ups, or…?
Josh: Well, I think that people who work in companies that look like mine. I use Canary kind of as an easy example because it is sort of in the wheelhouse of the type of company I’m talking about. But a lot of people who work for companies like that are sometimes doing things on their own. They have contemplated doing things on their own, perhaps they’ve done it in the past. But even working within the start-up environment, I think there’s a lot of independence, a sort of different, much more entrepreneurial way that you approach your work than sort of most – over-generalizing I’m sure – but most large company types of roles. So it’s necessarily that people are off starting their own businesses tomorrow. But these are people who have an entrepreneurial way of working and work in those types of environments.
Michael: Okay. I would just say that anyone who’s contemplating doing it has to be aware that it’s thrilling and terrifying at the same time, that you’re going to learn a lot more than you already know, for sure, but in its own way, it’s the ultimate form of security because you’re being hired and paid for talent that no one can take away from you. So if you’ve found the core that is uniquely yours in terms of where your talents lie, no one can ever take that away from you. And if you connect with clients who appreciate what they’re hiring you and paying you, there’s relieve on their part that they’ve found someone who does what they need to have done, so they’re not going to let you go. So that’s its own form of security which at face value look risky, but in reality, isn’t.
Josh: Yah, that makes sense, that makes sense. Awesome. Michael, thanks for joining us. People can find you at Baldwin.com. Congratulations on owning that domain. Are you on Twitter or anywhere else people can find you?
Michael: Yah. Be Better. Be_better_
Josh: Got it. @be_better_ on Twitter. Thanks so much for giving the time.
Michael: Okay, Josh.
Josh: Have a great new year. Take care. Bye.
Michael: Okay, bye.