How Creativity Motivates Manufacturing CEO - Richard Moross

In Chapter 11 of 17 in his 2012 interview, London entrepreneur and Moo.com CEO Richard Moross answers "What Role Does Creativity Play in What You Do As a CEO?"  Moross is driven by a need to make things.  He channels this drive in his design and manufacturing business.  Product innovation in the engineering and design continually renews Moross' purpose in his work.  Moross is founder and CEO of Moo.com and a leader in the London startup scene.  Before starting Moo.com, an award-winning online print business, Moross was a strategist at Imagination, the world's largest independent design company.  He graduated from the University of Sussex, where he majored in philosophy and politics.

Adapting British Business Culture for U.S. Expansion - Richard Moross

In Chapter 12 of 17 in his 2012 interview, London entrepreneur and Moo.com CEO Richard Moross answers "What Has Working Internationally Taught You About Communicating Across Cultures?"  Moross discusses taking his London, UK based company into the United States and the cultural and customer differences that have come with it.  He discusses the importance of understanding employees on their terms, for example knowing about commutes, and doing the same for customers, in particular how product demand varies by region.  Moross is founder and CEO of Moo.com and a leader in the London startup scene.  Before starting Moo.com, an award-winning online print business, Moross was a strategist at Imagination, the world's largest independent design company.  He graduated from the University of Sussex, where he majored in philosophy and politics.

When to Hire An Assistant and Get Your Life Back - Richard Moross

In Chapter 13 of 17 in his 2012 interview, London entrepreneur and Moo.com CEO Richard Moross answers "How Are You Learning to Better Manage Your Time and Commitments?"  Overwhelmed with work, Moross learns first to recognize and admit he has a problem and then, second, to do something about it.  He takes steps to hire an assistant and delegate responsibility, even things he feels he does better than anyone else such as managing his travel.  Moross is founder and CEO of Moo.com and a leader in the London startup scene.  Before starting Moo.com, an award-winning online print business, Moross was a strategist at Imagination, the world's largest independent design company.  He graduated from the University of Sussex, where he majored in philosophy and politics.

How CEO Learns When to Lead and When to Manage - Richard Moross

In Chapter 15 of 17 in his 2012 interview, London entrepreneur and Moo.com CEO Richard Moross answers "How Do Leadership and Management Differ in What You Do?"  Moross shares how his path or arch as a startup business founder has involved a leadership to management skills transition.  As he has experienced, it begins by setting a vision and sharing that destination with others.  Management skills require then setting the route and taking the team to that destination.  He sees leadership as sentiment and management as grammar and puts a team in place to help him evolve his role and grow the business.  Moross is founder and CEO of Moo.com and a leader in the London startup scene.  Before starting Moo.com, an award-winning online print business, Moross was a strategist at Imagination, the world's largest independent design company.  He graduated from the University of Sussex, where he majored in philosophy and politics.

Management Lessons on Adaptation and Commitment - Richard Moross

In Chapter 16 of 17 in his 2012 interview, London entrepreneur and Moo.com CEO Richard Moross answers "How Have You Learned to Adapt When Things Have Not Worked Out as Planned?"  Moross walks through specific instances where his company has adapted in the face of a mistake and turn lemons into lemonade.  He talks about the need to experiment and work through cycles of broadening and focusing strategy and why commitment and focus are critical to building the business.  Moross is founder and CEO of Moo.com and a leader in the London startup scene.  Before starting Moo.com, an award-winning online print business, Moross was a strategist at Imagination, the world's largest independent design company.  He graduated from the University of Sussex, where he majored in philosophy and politics.

Planning Hiring Strategy at a 100-Employee Firm - Richard Moross

In Chapter 17 of 17 in his 2012 interview, London entrepreneur and Moo.com CEO Richard Moross answers "What New Challenges Are You Facing as Your Company Grows?"  Moross notes his company has reached 100 employees and is now hiring a person a week.  He emphasizes 1) the importance of aligning new hires with the existing team; 2) telling the story of the company; 3) finding adaptable new hires and 4) ensuring he finds time to meet with an increasingly distributed and international team.  Moross is founder and CEO of Moo.com and a leader in the London startup scene.  Before starting Moo.com, an award-winning online print business, Moross was a strategist at Imagination, the world's largest independent design company.  He graduated from the University of Sussex, where he majored in philosophy and politics.

Joe Stump on How to Turn Past Mistakes Into Future Successes

In Chapter 4 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "What Role Has Reflection Played in Shaping Your Personal Growth?"  Stump finds reflection the only way to leverage past mistakes and turn them into future successes.  Stump writes a bullet point list of mistakes made at his previous company, SimpleGeo, and uses this to guide his next company, Sprint.ly.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University. 

Transcript:

Erik Michielsen: What role has reflection played in shaping your personal growth?

Joe Stump: I'm a big fan of learning from mistakes. I'm definitely a trial and error kind of guy, that’s how I learned how to program. You could make a solid argument, that’s how I've learned to start companies. So, I think that reflection is the only way that you can leverage your past mistakes into future success.

So I've spent a lot of time, particularly after SimpleGeo, reflecting and I actually wrote a long document, basically this long bullet point list. It was basically a punch list of things that I had messed up on and that bullet list, that punch list of mistakes basically very much guided me as I went on to create my next company.

Erik Michielsen: Can you give a couple of examples?

Joe Stump: Yeah. Yeah. I think, so, at SimpleGeo, I think we raised too much money too quickly and we hired too many people too quickly before we had really figured out what the product was fully going to be and how we were going to take it to market. So, basically everything was kind of done backwards.

So at Sprint.ly, I have the mantra of like -- I beat the drum of what I call the three S’s, small, slow, and steady. We're building a company that I hope to work at for possibly decades and you don’t do that overnight. So, that’s probably been the biggest lesson that I've taken away. We had amazing people and amazing investors and obviously plenty of money in the bank at the time but it was putting the cart before the horse in a lot of ways.

Joe stump on Staying Composed When Things Do Not Go as Planned

In Chapter 6 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "How Have You Learned to Adapt When Things Have Not Worked Out As Planned?"  Over time, Stump follows the idiom "don't cry over spilt milk" and not to get hung up on things that cannot be changed.  Stump keeps his composure through difficult times and continue starting, building, and advising companies.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University. 

Transcript:

Erik Mchielsen: How have you learn to adapt when things have not worked out as planned?

Joe Stump: I think there's a couple of things that I've learned over the years. I used to be much more hot-headed than I am now and I think that – I think I've done a lot better job of recognizing that when you're in a bad situation or things have kind of went off the rails of accepting that and triaging and moving forward.

Like I can’t -- the phrase is don’t cry over spilt milk. You can't do anything about the fact that the milk spilled. The only thing you can do now is go and get a mop and clean it up. And I think embracing that has been really important because quite frankly I mean, the last couple of years, I probably would have gone back to Michigan and just bought a farm, bought some sheep or some shit. I don’t know.

Joe Stump on How Family Relationships Change With Age

In Chapter 8 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "How Are Your Family Relationships Changing As You Get Older?"  Moving into his early 30s, Stump finds parallel between his business career journey and that of his father.  Stump notes the rewards of a newfound peer relationship with his father.  He also shares how he is helping his younger brother, "paying off a few of those wedgies" and how his Mom remains a constant source of support in his life.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University. 

Transcript:

Erik Michielsen: How are your family relationships changing as you get older?

Joe Stump: I think as I've gotten older, it's been interesting. Obviously, everybody else in my family is getting older and changing themselves, right? My dad, while I've been kind of climbing up the ladder, has also been climbing up the ladder. He’s been, you know, he was a late comer and he owned his own business for many, many years and then ended up going into a more corporate environment. And so, he’s been climbing up the ladder. He kind of started – kind of about the same time I did. And it's interesting with my dad.

It was obviously earlier on in life. It was -- Dad was the authoritarian figure. He was definitely somebody that I looked up to and taught me a lot of things about everything from how to install a furnace – he built homes for a living -- to how put worm on a hook. And that’s evolved to now, like he comes to me for advice every once in a while. I still seek out advice from him and then we talk and now we talk a little bit more like peers and that’s a big deal. My brother and I had a terrible relationship growing up. We basically fought like cats and dogs and hated each other. And now, I've been able to come back and kind of pay for past digressions and help him out in ways that my parents couldn’t help him out.

A good example of that is he moved out to San Francisco recently and I’ve an enormous network in San Francisco. You know, he moved from Michigan, the most depressed economy in the States, to California, which never mind the state debt is still a booming massive economy and I was able to get him a job there. And you know, that’s great. I loved to be able to help my brother out and pay off a few of those wedgies. I think the relationship that maybe has changed the least is really with my mom. My mom has always been someone who was -- always made me feel better about myself. I don’t think I'm ever going to be at a point in my life where I won’t need people that can help me feel better about myself.

So, my mom still likes to mother me and I don’t know if as a mama’s boy I’ll ever get tired of being mothered. It's kind of funny. My mom and I, to say the least, as a fairly conservative Midwestern housewife. Her and I have different style tastes you could say. Mom’s being mom. They always want to make sure that you're staying warm and all this other stuff and she would send me clothes that I had no interest in wearing. And I finally was able to take advantage of her mothering in a way that made her feel good while also making sure that I didn’t every time get a birthday present, take it to goodwill. And she now sends me -- it's like clockwork.

Every birthday and Christmas, I get a huge care package. I get usually a 24-pack of Bell's Oberon, I get a couple dozen sugar cookies, grandma’s recipe she sends. And it's amazing. It was like, my mom is so amazing because she is the type of mother that knows that my brother likes her sugar cookie recipe and she knows that I like grandma’s sugar cookie recipe. So Jonathan gets mom’s recipe and I get grandma’s recipe. And then like I asked for buckeyes because grandma used to make buckeyes.

For those that don’t know what buckeyes are, they are the most amazing treat. They’re basically peanut butter balls dipped in milk chocolate. They're amazing. I was like, “oh. I want some buckeyes”. So she sent me buckeyes. I don’t think I’ll ever get tired of that. My mom, she's always been kind of an emotional center for me and I think it will continue to be that way.

Joe Stump on Management Career Advice on Finding a Mentor

In Chapter 9 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "At This Point in Your Life, Where Are You Seeking Advice and Coaching?"  Stump references his goals to be a good businessman, programmer, partner, son, and brother.  He recognizes the domain specific nature of each and highlights the importance of cycling in new opinions regularly.  As his career responsibilities progressively become management focused, he turns to new mentors, including his father, who provide outside perspectives from different industries.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University. 

Transcript:

Erik Michielsen: At this point in your life, where are you seeking advice and coaching?

Joe Stump: A number of areas. I continue to leverage my Jedi Council. I have a number of mentors. I find that you can’t – I mean look, long term, I have to be a good businessman, I have to be a good programmer, I have to be a good boyfriend, partner, husband to my lady, and I have to be a good son and brother. And those each take different skill sets. And so, the mentoring that I seek out tends to be a little bit more domain-specific.

I also try to cycle new opinions into the Jedi Council. So, what I seek out now, like it's changed a lot. I used to lean heavily on a lot of programming mentors. I'm not programming as much anymore so I don’t really lean on them so much. I've actually been leaning a lot more on my dad when it comes to management. My dad’s a great manager. He’s done great things where he’s at and I like talking to him about that because he gives me an outside perspective from a completely different industry on how to interact and build employees up.

I have a friend of mine who is also kind of an engineering manager similar to me and he has this saying about employees. He treats employees, he thinks of employees like campsites and that you should leave them better than you found them. So, getting that outside perspective, I think is really important. I think it's been a really great bonding experience. My dad now calls me and will ask me questions about management, which I think is kind of funny.

So yeah, so what I look for in a mentor has definitely evolved over time because my career has evolved. Like, I'm no longer – I’m not sitting and banging out 10,000 lines of code a day. I'm managing, I got to do accounting now, I got to do – like I’m management benefits, I got to talk to lawyers, I have to read contracts. So yes, seeking out different advice now from different people has been pretty important.

Joe Stump on Bringing Entrepreneurial Optimism to Cynical Cultures

In Chapter 10 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "What Has Working Internationally Taught You About Communicating Across Cultures?"  By advising a British company, Stump learns how a culture of optimism contrasts with a culture of cynicism and doubt.  He compares general country cultures - American, British, Indian, Chinese - and how an entrepreneurship mindset is influenced by the national mindset.  He details what he did to transform the mindset inside that British company to be more opportunistic and confident.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University.

Transcript:

Erik Michielsen: What has working internationally taught you about communicating across cultures?

Joe Stump: I'm an adviser for a company in the UK. I go over there and I spend about a week every quarter over there. And I think Americans and Brits kind of like to think that it's big brother, little brother, we're in the same family. Our cultures are drastically different in a lot of ways and I think working with them -- it was really disheartening to come from the startup world where everything’s “can do” attitude and go to an environment that -- I mean this was named, the company I work for is named one of the top 50 companies in the UK to work for.

They're a great company. I love working with these guys. But there are little things that really kind of trick you up that were kind of like a bummer. Like, in the United States, a grilled cheese company got $50 million in funding from one of the best venture capital firms in Silicon Valley. That is the very definition of like all ideas go. It's wide-open space. There are more eternal optimists bred everyday in the United States than anywhere else, right? The American dream is basically if you want to do it, it's yours for the taking, whereas in I talk with -- Alex Hunter is a buddy of mine. His wife is from California. He spent considerable time here. Actually he doesn’t even have a British accent anymore, he spent so much time here.

But he’s from Britain and he’s put it best to me, in Britain, I mean, everybody knows that they have a very cynical sense of humor right? And I think that pervades the entire society. Where he says, “You come up with a new idea,” and like British society will go, “Oh, you have a new idea? Let's see if it flies.” It is like poopoo it before it's even had a chance to even get out on the launch pad. And working with that company in the UK has taught me that when I come in and I’ll say, “Hey, guys, we need to do X, Y, and Z so that we can move on to this next phase.” They will be, “Well, we really can't do X because of A, B, and C.” And I'm like, “You can do X. What you're telling me is that you don’t want to do X because of A, B, and C. You can fix A, B, and C.”

There is no unsolvable problem, right? And I think that’s something that really comes up a lot across Europe. They're a lot more conservative I would say. Exact opposite when you go to India and Asia. Man, those guys are like, it's wide open territory. I mean, like, dude, China is growing. That is a massive economy, a billion people and it's growing at 10 to 12% a year. It's really interesting. You go to all these different places and the emphasis because of culture, like emphasis in South Africa, for instance, is on revenue, early revenue. A lot of the investment deals are all tied to revenue goals and stuff.

Europe is a little bit similar. The United States they’re like nobody thought Facebook was ever going to make money and now it's making $4 billion a year. Right? And because of our culture, we're a lot more open to risk and we’ll go ahead and take that. And I think that now that other major economies are starting to sputter to life and they're starting to get their own version of the American dream, India and China, I think are two very good examples

There are a lot programmers in India that are just like starting to realize that they don’t have to work at call center. They can go and they can raise a small amount of cash and they have a billion people there that are all ready to pay a little bit of money. If you can get a billion people to pay you 10 cents, that’s real coin, right? So, they're embracing it. And also because travel is becoming cheaper, obviously they're making more money and their economies are coming up so they're able to come here. It's been really interesting to see that the America dream is alive and well and it just happens to be in a communist country and India, which is a socialist country. It's been interesting.

I like interfacing and talking with people like that. I like spreading the dream. Like and I've been telling -- we actually had a little luncheon at the company in the UK and they were like, “What's the most frustrating thing about working with us?” I was like, “You guys are so much better than you give yourselves credit for. Quit being so cynical.” You can do it. You just got to like go do it. This isn’t like rocket science stuff here. Every time I’m like, I come up with something like, “We need to fix this,” and they're like, “Well, maybe we should probably do this other thing instead.” It’s just like…Just do that, get it over with, move on to the next thing.

It was kind of funny. There was actually some nodding in the room and then afterwards one of the guys came up to me, he's like, “I'm really glad you said that because I didn’t even realize that I was doing that. And now I realize that I'm poopooing stuff that I know I can do and I don’t even know why I'm doing it. I don’t know why I'm poopooing this. I can do it.” It was really cool that they were like, “Yeah, we can do that.” They’ve really grown as a company. I’ve seen them -- It's a 1,200 person company and I've seen them move more, and more quickly, they're getting a lot more confident that they can take on those bigger challenges. I didn’t have a whole lot to do with that other than basically saying you know, telling them that, “Look, guys, you can do this. You just got to do it.”

Joe Stump on Startup Founder Advice on Working With Venture Capitalists

In Chapter 11 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "What Were the Main Learning Points From Starting and Selling a Company?"  Through starting and selling SimpleGeo, Stump gets a clear understanding of how the sausage factory works in the VC land. He first learns the Internet startup talent ecosystem - programmers/builders, luminaries/speakers, founders, and investors/venture capitalists - and, in particular, how the game is played at the top of the investing scene.  He turns a founder frustration - how venture capitalists overshare information - into a founder strength. 

Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University. 

Transcript:

Erik Michielsen: What were the main learning points from starting and selling a company?

Joe Stump: I don’t even know where to begin. The main learning points that I took away from SimpleGeo, I think, were I got a very clear understanding of how the sausage factory worked in the VC land, right? There are a few layers of sediment in the startup world. There are the implementers, the people that are banging out code, they're writing design, stuff like that. Slightly above them are the luminaries in that area, right? They are the people that go and speak at conferences about the new Java script frameworks that they're writing, and things like that.

One kind of layer above them are the founders. Those are people that go out and have a crazy idea and decide they want to build a company. And then the layer above that are the investors and VC. And you really don’t have any insight into what's going on until you kind of like move your way up. So I got a very clear, terrifying view of what that top layer is and understanding how that works was important to my long-term success. You have to know how the game is played.

Erik Michielsen: How is the game played?

Joe Stump: That game is like Lord of the Flies on steroids. I mean, it is cut throat. You know, people will -- There's so much drama that happens behind that investing scene that nobody sees. There are things like -- you talk to entrepreneurs, other founders. I call being a founder, being a part of the fraternal order of founders. You just don’t know what it's like until you’ve like actually been in it. I've had founders tell me, “I want to raise money from both of these guys but this guy won’t invest if this guy invests.”

I've had other people tell me that investors have called them and threatened them with their livelihood if they don’t do a deal in the way that they want them to do it. Investors gossip non-stop like even if you sign – even if they're a board member and they have a fiduciary responsibility to keep their mouth shut, they’ll gossip all day long. So understanding -- The biggest lesson I took away from that is like you can't trust anybody. But what you can do is leverage that.

Something that I've been doing more recently and the ways that you can kind of leverage that -- I probably shouldn’t be saying this but, is I know that if I go and tell somebody that so and so is doing really well and if I can strategically leak positive information about a company that I've invested in or I'm an adviser in to other people that are like -- and get out ahead of that company.

A good example of something that I might do is in a company that I'm advising in or invested in, I have deep insight into what's going on, right? And I usually have a strategic six to twelve-month window ahead of what they're planning on doing. And if I know that bits of data over here are going to help them six months from now and they're going to need this person or this firm or this capital in six months, I can leverage that gossip in the way that -- and that distrust and basically deploy knowledge ahead of time and just set the stage up ahead of time.

And I think one of the biggest lessons I had that I took away from -- really from all that experience is I love sausage but I hate the sausage factory. I don’t want to know how it's made, right? So I've tried to remove myself from that a little bit. And I think the other lesson that was really hard for me to swallow, you hear about really crappy things happening to good people and what's really frustrating is these people that are doing really crappy things are being exalted. These investors are being exalted on every blog, tech blog and everything as being like -- All they do is help founders. Well, I know for a fact that people that you say help founders have destroyed founders. So, don’t tell me that that’s actually how it happens.

The thing that was really difficult for me to accept was people would say “it's just business”, which is the MBA way of saying, don’t hate the player, hate the game. There are a few players that I legitimately hate because they have strayed way beyond what I think is acceptable human interaction but it has allowed me to embrace the parts of the game in a way that allows me to work with people that probably otherwise I wouldn’t want to, in a way that benefits everybody.

Joe stump on How an Entrepreneur Learns the Startup Investing Game

In Chapter 12 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "How Have Your Entrepreneurial Pursuits Taught You to Be a Better Investor?"  After raising money for three companies, advising a venture capital firm and investing his own money in three companies, Stump shares what he has learned about startup investing.  He describes the portfolio theory approach VC firms take and how as an entrepreneur he has learned to compete as a portfolio firm.  He learns the mechanics of angel, seed, series A and series B investing and how to negotiate contract terms.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University. 

Transcript:

Erik Michielsen: How have your entrepreneurial pursuits taught you to be a better investor?

Joe Stump: So, I've been involved in a number of ways with venture capital, raising money. I've raised money now for two companies myself and I've helped a third company raise money as well. I'm a fund adviser for Freestyle Capital and I've invested my own money into three companies now. And the things that I have learned are that there are billions of dollars that are being deployed in what at times appears to be a very chaotic manner.

VCs work off of portfolio theory. They invest in a hundred companies and they expect 95 of them to fail for the most part. And what that lesson taught me as an entrepreneur is if you're one of those 95, guess what, you are competing with 95 other people for probably 20 percent of their time because they're spending the other 80 percent of their time on the five winners. So, that’s a harsh reality to learn but it's good to know and I think that there are times when getting the attention of your VC and your investors can actually be a bad thing. I mean, not that they're bad people or whatever, but it's nice to sometimes work without having the pressure.

So, I know founders that will withhold good information for just a little while longer so that they can have a little bit more breathing room and then they're like, “Ta-Da! We're one of the five!” and then the VCs are like, herd over. And they’re like …  and they bear hug them, you know, and they’re like oh god. It's like when your mom gives you a hug, you're like, “Mom, stop.” You know.

So, that’s been interesting to learn about. The way that... What's been really fascinating to me is like someone like me that dress like me, looks like me, says the F word as much as I do, can walk into a guy’s office who manages billions of dollars and then I’ll show him -- well, with my last company, I didn’t even have a PowerPoint presentation. I didn’t even have a presentation. I had a financial model in Google Docs, a product document, and a prototype and they were just like, “Oh yeah. Let me pull out the check book, and just write you a giant check with lots of commas in it” and you're like, “Really?” It seems -- Growing up in a blue color family in the Midwest, it seems like you're cheating somehow, like you're stealing money or whatever. So, that’s been really interesting.

A lot of people on the outside view it as like oh this – that the firms don’t really talk with each other and that they're always competing and they do compete for deals. But it's not really like that at all. They talk a lot to each other, they will actually -- I won’t say fully collude but I mean there are a lot of times that the VCs are back channeling with each other a lot more than entrepreneurs really realize. And then you just learn the basic mechanics like I know now that Angel investors, depending on the Angel investor, they want between a half a point and one and a half percent. They want enough that we’ll take their $20,000 to $100,000 investment and turn it into a million dollars, right? If you're the first point and a half in, that can happen if it’s one of those five companies.

I now know that seed stage, they generally want between 12.5% and 17% of the company. I know that the series A wants 20 percent, series B, things start going back down because hopefully by then you're making money and what not then looking at more anywhere between 10% and 20% and the C is definitely kind of in the 10% range. So the basic mechanics of understanding how that game is played has been invaluable to me.

I've been able to negotiate better terms for myself, I have been able to…I advise a number of companies, I've been able to return sheets over and tell them, “Hey! Maybe we shouldn’t do that. Maybe we should do this,” and getting clear insight into how the VCs interact with each other and who likes who and who doesn’t like who and how they work together has made me a much stronger -- I won’t say opponent, but like when I go into the ring with those guys, like I know who’s going to say what to who and how that’s going to all work out. And knowing the players in the game makes you a better player.

I almost feel like one of the best defensive basketball players of all time: Dennis Rodman. That man watched hundreds of thousands of hours of video and it was all so that he could know his players, his opponents inside and out. And being an adviser, being a fund adviser, investing my money, et cetera, that’s my way in to understanding the game and my opponents and who I'm going to be going up against as far as the next -- who goes on down the line and getting insight into their mentality.

I read an interview once about Dennis Rodman and they were talking about how much of a fanatic he was about watching tapes and he got so good at it that he could literally say by the time the guy flicked his wrist – so you’re talking about the ball is maybe one-third of the way to the rim. He will be like, “That’s going to bounce off the back of the rim off the left side. That’s going to bounce off the front of the rim straight down the lane.” That’s how good he was. Doing that has taken me from being a blue-collar kid that grew up in a cornfield to somebody who can negotiate contracts with some of the best MBAs that our country has and it's really fun.

Joe Stump on Learning Entrepreneurial Business Skills From Lawyers

In Chapter 13 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "What Has Working With Lawyers Taught You About Business?"  Stump learns basic employment and contract law during college business law classes.  As an entrepreneur, Stump learns far more about how to mitigate and minimize risk as a startup founder and business owner, for example, reading contracts to filing tax forms.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University.  

Transcript:

Erik Michielsen: What has working with lawyers taught you about business?

Joe Stump: It has taught me a ton. I went to business school in my undergrad, so I actually had to take some law schools. I'm sure you had to as well. And it’s just like -- The law classes I had to take, I think I had to take two of them and they're very basic employment kind of law classes. But they do give you a window into how contracts work, like what is the basic you need. You need mutual consideration in a contract. What are the basic things? So I at least had that luckily because a lot of my peers that are programmers that become founders, they get this legal paperwork, and they’re like, what do I do?

But the things that the lawyers have taught me over time is basically what to look out for in contracts. The lawyer’s entire job – their entire job is to mitigate and minimize risk, right? And so, they’ve really taught me that your business is under constant attack and you have to watch out for that. A lot of us, a lot of business people think that the attack are competitors or market environments. The attacks can come from within like employees, partners, clients, investors.

So, you need to basically -- the lawyer is there to help you navigate those tricky waters and there are so many laws out there and so many ways that you can structure contracts that I didn’t even know existed until I started working with lawyers in and around my business. It's made me so much smarter and it's actually allowed me to even move more quickly, it saves me money. I was talking to an investor friend of mine. There are a couple of really common mess-ups that founders do in startups.

First of all is they don’t get contracts for consultants. So, early on, you're moving really, really quickly. You're like, “I just need this code down. I need another set of hands,” and then you just hand out a GitHub key and people start hacking and then the problem with that is if you don’t have a contractual relationship with somebody and you just have like a couple of emails and IMs, that does nothing but cause your lawyer to lose his hair, right? Because that person, there are automatic employment laws in a lot of states, particularly in California. California has some very European-esque employment laws.

So, watching out for that has saved me money. Personally, myself in a company early on in SimpleGeo, my co-founder hired a contractor and we ended up at the time, we didn’t end up getting paperwork and it end up costing us, when we ended up letting that guy go, a lot of money.

Another common mess up is there's this thing called an 83-B and you're supposed to file this with the IRS when you get equity in a company and that starts your capital gains clock ticking. That’s something lawyers do. It's just kind of automatic stuff. My co-founder in SimpleGeo at his first company did not file that and that was the difference between 15 percent tax rate and a 48 percent tax rate when he sold his company and he ended up paying 33 percent more in taxes than he should have.

So, what I’ve basically learned from my lawyers is -- it's interesting. I've learned a couple of things. First of all, I learned how to read contracts and I know what to look out for, which actually is kind of ironic. The lawyer has basically trained me up to the point where I'm like a junior paralegal and I'm like saving myself money. So I redline and read all the agreements that I get before I go back to the lawyers. The other thing, and it saves me money with employees, it's saved me money with taxes. I very, very happily write my check to my lawyer. Accountants, they're very similar. Those are the easiest checks for me to write along with my employees.

Joe Stump on How to Make Product Management Easier for Developers

In Chapter 14 of 14 in his 2012 interview, Internet entrepreneur Joe Stump answers "How Are You Learning to Improve the Product Management Process for Developers?"  Stump provides the background for what motivated him to co-found software company Sprint.ly to make product development easier.  Joe Stump is a serial entrepreneur based in Portland, OR. He is CEO and co-founder of Sprint.ly, a product management software company.  Previously he founded SimpleGeo, which was sold to Urban Airship in October 2011.  He advises several startups - including attachments.me and, through its acquisition, ngmoco:) - as well as VC firm Freestyle Capital.  He earned a BBA in Computer Information Systems (CIS) from Eastern Michigan University.

Transcript:

Erik Michielsen: How are you learning to improve the product management process for developers?

Joe Stump: I talk to a ton of developers and just listen to what they're doing. I do a little bit of consulting as well mostly around product management and team management, a little bit around product as well. I think product management spans a big area. It spans strategy, what should we build, when should we build it, why are we building it, all the way to asset allocation and whatnot.

So, basically I've been working in this space. I've been leading and managing teams for almost a decade now and I've kind of taken a lot of those lessons and what I find is every team behaves slightly differently and the thing that I’ve probably – the thing that’s stuck out most to me over the last kind of decade or so is that when you assemble teams, like each team is like a little snowflake and they all behave and look and act in a slightly different manner. And in software engineering, there’s like, there are all this process paradigms, agile, scrum, waterfall, kanban.

And what I found is teams generally will embrace parts of each of those. Very, very few teams will embrace those fully. And what I’ve done is – I mean every developer at some point in their career has been frustrated with one of their tools, and said, “One day I'm going to rewrite a better mousetrap and I'm going to make a better tool.” And I'm happy to say I'm realizing that dream finally.

I recently -- The first week of December, I launched my new product. It's called Sprint.ly. And Sprint.ly is really the manifestation of almost 15 years of frustration with the product management tool. These tools I found have generally fallen into a couple of different camps. One camp is they're built for product of business to manage resources. Developers hate those. They don’t really like using those. They don’t have a lot of things that developers want and for, to do their day to day stuff. So the features in those skew much towards really resource planning. And then you have bug trackers built by developers for developers.

So you have two completely different types of software that are trying to address the same problem for two different parties at the table, right? Really my approach with Sprint.ly has been I think a little bit different whereas in first of all, I'm trying to build a tool that unifies those two camps. I actually found more than a handful of customers when I was talking to them that the developers were literally using one tool and the project management people were using another tool and then they would copy and paste stuff back and forth, which I think is insane.

So, we've been building Sprint.ly in a way that I want to get everybody using the same tool. So that has forced us to decrease barriers. And we built a tool, a lot of the tools out that are in product management, certainly the bug trackers are very technical and very difficult to understand. So we've kind of done away with that. It looks a little bit more like a consumer product. And the other thing I wanted to do is I wanted to increase transparency. So I talked to – you talk to the developers and it's almost like companies in software – like software companies are two black boxes warring at each other.

You have the makers on one side and you have the business and manager people on the other side and they're like, “What are you doing?” and the other one is like, “What are you doing? Why are you doing that? Why are you doing that?” So really, I want to build Sprint.ly kind of into the UN of product management software where everybody comes to the table, everybody can see what everybody else is doing. I think sometimes my software development peers make things a little too complicated.

I guess over time, I’ve just learned that when you're building products and working with teams that you need to spend more time listening than talking because that’s when you'll realize what the problem is. There's a couple good quotes around product that I like that I think emphasize that, which is “don’t give the customer what they ask for, give them what they want.” And then there's a really great Henry Ford quote, which is, “If I had asked my customers what they wanted, they would have said faster horses.”

Jon Kolko on Finding Joy Changing Careers From Business to Teaching

In Chapter 3 of 21 in his 2012 Capture Your Flag interview, design educator Jon Kolko answers "What Do You Enjoy Most About What You Do?"  Kolko discusses making the transition working as a design professional to teaching design at the school he founded.  He discusses the rush he gets in the classroom and across parts of the "ivory tower" experience such as reading, researching and writing about complex problems. 

Jon Kolko the founder and director of the Austin Center for Design.  He has authored multiple books on design, including "Wicked Problems: Problems Worth Solving."  Previously he has held senior roles at venture accelerator Thinktiv and frog design and was a professor of Interactive and Industrial Design at the Savannah College of Art and Design (SCAD).  Kolko earned his Masters in Human Computer Interaction (MHI) and BFA in Design from Carnegie Mellon University.

Transcript: 

Erik Michielsen: What do you enjoy most about what you do?

Jon Kolko: I loved everything about design. I just love being a designer doing creative design work, making things. I've sort of transitioned in the last couple of years. So being called an academic has always sort of stung me like ah, that’s bad. In the last three years, I've decided that in fact, I am an academic and it's good. And so, I think in the same sort of excitement and personal rush that you get from doing creative design work. I also now get from teaching. And so, that’s sort of have been a revelation to me that it's okay to live in an intellectual ivory tower to some degree as long as you make that ivory tower accessible. I don’t feel bad that I enjoy reading and writing and thinking about complex problems. And so, for me, that’s been something that’s been making me really, really happy recently is any time I can spend actually teaching in a classroom. Weirdly, I'm spending less and less time teaching in a classroom because as the Austin Center for Design is more successful, there's more administrative crap to do. I don’t mind doing the crap. It's called crap because it's not fun but it's also not bad because it's still my baby. I'm still really enjoying it. I could see in the future that would definitely be something for somebody else to do but for the time being, anything that’s related to teaching and design is really, really giving me a lot of pleasure.

Jon Kolko: Why Entrepreneurial Leadership Starts With Passion

In Chapter 5 of 21 in his 2012 Capture Your Flag interview, design educator Jon Kolko answers "What Does It Mean to Be a Leader in What You Do?"  Kolko looks at what he has learned about developing as a leader through the lens of his students.  For him, he sees drive, passion, resiliency and curiosity form the foundation that help select entrepreneurs thrive professionally and lead in their respective fields.  Jon Kolko the founder and director of the Austin Center for Design.  He has authored multiple books on design, including "Wicked Problems: Problems Worth Solving."  Previously he has held senior roles at venture accelerator Thinktiv and frog design and was a professor of Interactive and Industrial Design at the Savannah College of Art and Design (SCAD).  Kolko earned his Masters in Human Computer Interaction (MHI) and BFA in Design from Carnegie Mellon University.

Transcript: 

Erik Michielsen: What does it mean to be a leader in what you do?

Jon Kolko: I think that there are a lot of things around confidence that play into leadership. I think there’s qualities of charisma but I don’t know. I feel like those are ancillary. I feel like there's something else at the core and it might actually have to do with drive and passion. I have a hard time looking at myself through that lens. 

So maybe we could look in some of my students through that lens and the students that are most successful in starting companies, meaning in becoming leaders, seem to have an unending passion for whatever it is they're doing. And so, when you do anything in design or business, it's a constant struggle. When you start your own company, which you know it's a huge constant struggle and it almost feels from one perspective like anything that can go wrong will go wrong over and over and over, and it takes a certain unending passion to get through that because it's very easy and it's almost like the logical thing to do is to give up and at some point to just throw in the towel and say it's easier to go to work for somebody else or do something else. But I've just seen in the students that have graduated that have formed these companies and then going on to be successful, each time something sort of difficult or complicated comes at them or a reason why they should give up, the ones that are truly passionate about it don’t and use it to somehow gain leverage on a situation to turn it into something positive. 

That probably begs the question of what is passion and I'm not sure I have like a ready flip answer for it, but it does seem like just a massive curiosity and a need to know things, and that passion in the context of a business is contained within the business. But generally it's just a thirst to know how the world works right? And how people are and why things are the way they are.

Jon Kolko on How Learning Facilitation Skills Advances Career

In Chapter 11 of 21 in his 2012 Capture Your Flag interview, design educator Jon Kolko answers "How is Your Creative Toolbox Changing?"  Kolko notes how his creative toolbox progressively includes "grown up" tools.  He notes these are more about talking and less about making, for example facilitation tools and those that help drive large organizational and strategic change.  He contrasts this to the design or maker skills so fundamental to his early career experiences. 

Jon Kolko is the founder and director of the Austin Center for Design.  He has authored multiple books on design, including "Wicked Problems: Problems Worth Solving."  Previously he has held senior roles at venture accelerator Thinktiv and frog design and was a professor of Interactive and Industrial Design at the Savannah College of Art and Design (SCAD).  Kolko earned his Masters in Human Computer Interaction (MHI) and BFA in Design from Carnegie Mellon University.

Transcript: 

Erik Michielsen: How is your creative toolbox changing?

Jon Kolko: My creative toolbox is starting to have much more grownup tools in it, which usually mean things that are about talking and not things about making. And it's weird that that is true. And so, the examples that I'm thinking of are facilitation tools and tools that help drive large organizational and strategic change as opposed to tools for making things look a certain way, act a certain way, feel a certain way. This strategy, design thinking, whatever catchy name you want to use for it, has always sort of rubbed me a little bit the wrong way because I’d always felt like it wasn’t enough without the making. And so, I think I still believe that. But I'm becoming okay with using a designerly way of working to convince people of things, to get people to see my perspective, to drive an argument. And that will be the way that design plays out in policy and in law. I mean, design is going to be embedded in all of these external disciplines or fields and that’s how it's going to work. There will still be artifacts but that’s not the endgame, they’re a means to an end and I think the toolbox that I have is widened to include those. Before, frankly, I didn’t give them the time and day. I thought they were sort of fake. I still have that same concern that without making an artifact, and I'm using artifact loosely, even digital or a service is an artifact to me but without making something. You're not doing design work. You're doing something else and it's probably just argument. But I'm becoming more comfortable integrating those issues of argument a rhetoric into the toolkit that I have.