Mike Germano on Why Brands are the New Venture Capital Investors

In Chapter 19 of 20 in his 2013 Capture Your Flag interview, Carrot Creative social media agency CEO Mike Germano answers "Why Do You Believe That Brands Are the New Venture Capital Firms?"  Germano finds there are progressively more ways for entrepreneur designers and developers to find money.  What Germano thinks is key now is distribution and he finds large brands have this distribution and also have innovation constraints.  With their innovation needs, access to investment capital, and distribution, Germano sees brands as the next generation of venture capital firms. 

Mike Germano is co-founder and CEO of DUMBO Brooklyn-based social media agency Carrot Creative.  Previously, Germano ran for and was elected to public office in Connecticut.  He is a graduate of Quinnipiac University. 

Kyung B. Yoon on How Reflecting Back Can Move Your Career Forward

In Chapter 1 of 17 in her 2013 Capture Your Flag interview, non-profit executive Kyung B. Yoon answers "What Role Has Reflection Played in Shaping Your Personal Growth?"  Yoon uses reflection to think about work she enjoys doing and work where she excels.  This process helps Yoon figure out what next steps to take in her career and find ways to eliminate inequalities and inequities and create social impact. 

Kyung B. Yoon is the executive director of the Korean American Community Foundation (KACF) in New York City.  An award-winning journalist and documentary film producer, Yoon earned an MA in International Relations from Johns Hopkins University and a BA in History and Political Science at Wellesley College.

Jullien Gordon on How Family Relationships Change With Age

In Chapter 3 of 21 in his 2012 Capture Your Flag interview, business coach Jullien Gordon answers "How Are Your Family Relationships Changing As You Get Older?"  Getting married in July marks a huge milestone in Gordon's life.  Additionally, Gordon turns his attention to thinking how he will care for his aging parents from a distance and what role he will assume in that relationship.  Jullien Gordon is a high performance coach and consultant to organizations, individuals and teams who want to increase employee performance, motivation, engagement and retention.  He earned a BA from UCLA, an MBA from the Stanford Graduate School of Business, and a Masters of Education from Stanford University.

Transcript:

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

Jullien Gordon: First and foremost, I got married. I got married in July, so that’s been exciting this year. And of course, as you get older you start looking at your parents as opposed to adult to kid, you start looking at them eye to eye and you’re able to have different kinds of conversations than you were able to have when you lived in their household, or even when you were in college and not as independent.

I find myself having to think about how I’m going to take my—take care of my parents, especially as my mom gets older, or just trying to take on that responsibility, understanding what my role is in that relationship. We are—she’s in California, I’m in New York, and just trying to figure out how do I create my life as I build my family, but still support my mother in her—I don’t wanna call it aging, but as her life continues, how do I support and be a good son from a distance, if I don’t happen to move back to California, so that’s been challenging, thinking about that, ‘cause here I am, a newly wedded husband and I have my wife to take care of, we don’t have kids yet, but at the same time, I feel like I’m starting to have to think about how I’m gonna take care of my parents, and so that’s an interesting dynamic, and I didn’t picture it being that way as I was growing up. You know, your parents take care of themselves and then you start taking care of your family, as your family takes care of its kids and it goes that way, but… So I’m finding some interesting dynamics as I explore being a son and being a husband.

Jullien Gordon on What It Means to Be a Leader

In Chapter 11 of 21 in his 2012 Capture Your Flag interview, business coach Jullien Gordon answers "What Does It Mean to Be a Leader in What You Do?"   Gordon notes the importance of having original thoughts and following to lead.  This gets him in a place where he can identify opportunities in his field and use his iteration process to release products and services that put him in a leadership position.  Jullien Gordon is a high performance coach and consultant to organizations, individuals and teams who want to increase employee performance, motivation, engagement and retention.  He earned a BA from UCLA, an MBA from the Stanford Graduate School of Business, and a Masters of Education from Stanford University.

Transcript:

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

Jullien Gordon: I think being a leader means having original thoughts, not just following the steps or the path that was currently laid out for you by, perhaps the original pioneer in your space. And so I like the notion of not following the leader but following to lead. At some point, the leader in your space is going to transition, exit, or go in a different direction and you have to say, “okay, I’ve been following and learning for this long from this person, but what original, authentic thoughts are coming through me that I need to bring into the world and bring forth?” So it really means being you at the end of the day because nobody can be you better than you, and while you may have someone who guides you for quite some time, ultimately you have to find out what is your authentic message and voice, and I think that’s what makes you a leader in whatever space it is you choose to operate in.

Erik Michielsen: What role does the trial and error process play in that leadership development?

Jullien Gordon: My whole life has been a journey of failing forward. I’ve made a lot of mistakes from losing amazing team members to unsuccessful online product launches to errors in written documents and published documents, and I constantly learn from that. I’m more of a get-it-done than a perfectionist, I used to be a perfectionist but now I’m more about getting it done and you can tell from my Good Excuse Goals book that it’s about getting the product out and then iterating from there, and getting it at least 80-90% right but not trying to get it 100% right and so. I recognize the consequences of moving in that way. But for me, even with mistakes and errors along my journey, my life has continued to impact other people’s lives. Whereas if I was trying to make things perfect, I still may be in cubby hole somewhere trying to make things perfect before I show it to the world, and my 80-90% right things have been out in the world and people have found them valuable and been inspired by them. And of course I need to close the gap over time but that’s the process for iteration for me.

Lulu Chen on How Reflecting Helps You Plan for the Future

In Chapter 3 of 16 in her 2012 Capture Your Flag interview, art director Lulu Chen answers "What Role Has Reflection Played in Shaping Your Personal Growth?"  Reflecting helps Chen appreciate what she has today.  It helps make better career plans, especially as she has grown into her 30s. 

Lulu Chen is a photo art director working in retail e-commerce in New York City.  Previously, Chen worked as a freelance stylist for leading fashion catalogs and magazines.  She earned a BFA in design and art history from the University of Michigan.

Transcript: 

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

Lulu Chen: I think it’s given me perspective just reflecting back on previous jobs and like life experiences and relationships. It’s—I don’t know. It makes me appreciate what I really have today, and it gives me perspective on what’s really important and what my priorities are. 
I think when I was younger I just kept working so hard but I didn’t necessarily think about the direction, you just think, “Oh, you just work really hard. You just keep doing this, and good things happen,” which generally I—you know, I try to be positive and hope that that’s still true, but sometimes I think you also have to strategize directionally, you know, sort of—kind of plan it out a little bit, and I’ve gotten better at that too as I’ve gotten older.

I think sometimes speaking to some of my friends, my peers, and having them kind of compliment me or point things out, that’s when I reflect back, and I really appreciate it, you know. It’s very hard for me to take compliments sometimes and I also—Yeah, I just forget, you know? I forget to stop and just think about things and, you know—just, you know, keep going.

Hattie Elliot on Why Travel to Distant and Unfamiliar Places

In Chapter 3 of 19 in her 2012 Capture Your Flag interview, female entrepreneur Hattie Grace Elliot answers "What Have You Found Most Rewarding About Traveling to New Places?"  Elliot notes how she find motivation to travel by her curiosity and interest in learning about family dynamics and social dynamics of different cultures.  Additionally it teaches her to value her liberty, freedom, and security she has as a United States citizen.  Hattie Grace Elliot is the founder and CEO of The Grace List, a social networking company that creates destination events and experiences to forge lasting personal and professional connections across its young professional members. Elliot graduated from the University of Cape Town in South Africa, where she studied economics, philosophy, and politics.

Transcript: 

Erik Michielsen: What have you found most rewarding about traveling to new places?

Hattie Elliot: Wowsers… I’m just a curious person. I love to experience the different cultures, and everything that comes along with that, the tastes and smells. And, you know, the different relationships people have with their careers, with their family, like family structure, and the way they treat their elders and their children, and the way elders treat their children, and the way that, you know, they—that they—their expectations on different, everything from homosexuality to marriage to political affiliation. I find all that stuff really fascinating because I think—especially in a place like the States, it’s very easy to become content and think that, you know, it’s our way or the highway. You drink the Jesus juice. 

And, you know, when you step outside of that box, I think in many instances, you—it gives you a new perspective and you’re able to realize that there’s other ways to think about things and other cultures that have really wonderful qualities that are really valuable, and that we can really deduce a lot of value from and really benefit from here, and personally, you know, things that we can take lessons from. And it also—on the other end, really makes you realize in many circumstances how lucky we are for certain freedoms we have, especially for me, I lived in South Africa for so many years and I love that country, but, you know, I really appreciate now more than ever how much freedom I have to travel, to speak my mind, that I’m safe, that I don’t have to lock my car door and worry about that every single time I step into my car, or walk into my apartment. 

So I think it just—it’s good for everybody, it’s—it gives you a better perspective on the world that it’s something that challenges you to—to just, like, any of these things to really, you know, reevaluate the way that you think about life in the world, and your home, and your friends and your family, and your everyday life, your career, all aspects.

Hattie Elliot on How Family Relationships Change With Age

In Chapter 7 of 19 in her 2012 Capture Your Flag interview, female entrepreneur Hattie Grace Elliot answers "How Are Your Family Relationships Changing as You Get Older?"  Elliot shares how as you get older, you have a choice on how much you want your family involved in your life.  She notes family relationships are rarely normal and Elliot talks about not only accepting different types of family but also viewing close friendships as family.  Hattie Grace Elliot is the founder and CEO of The Grace List, a social networking company that creates destination events and experiences to forge lasting personal and professional connections across its young professional members. Elliot graduated from the University of Cape Town in South Africa, where she studied economics, philosophy, and politics.

Transcript: 

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

Hattie Elliot: Well, I’ve always been really close with my family. When you’re younger, you know, you’re stuck at home and you kind of are born into whatever situation you’re born into, you don’t have much of a choice. But as you get older, you can really choose to a capacity, you really want your family involved in your life, and I really, really value my family. And I also feel like your friends, especially as you get older in a place like New York, also become kind of your surrogate family as well. I’m fortunate that I come—my mom’s from a big wonderful Midwestern family. My dad’s from a super dysfunctional small New York family. So it’s kind of a comedy there is the two. 

But I’m very close to my family, to both sides and to my parents. And I continue to stay close, but what I also really love is, through the years, my close friends, whether I’ve known them from kindergarten or even the last two years, have really also become my family. And part of, you know, my family here in the city, but also part of my extended family. Because I really think family is what you make of it. We don’t—I feel very fortunate for the family I was born in to but not everyone has that, but what you do have as an adult is the ability to create and craft a life for yourself and the family for yourself that makes you happy, that gives you pleasure, that’s your own. And that doesn’t necessarily have to be biological. It’s what you make of it. And so I think that’s been really wonderful how my friends—my close friends have, you know, become part of that, have become part of my family.

Finding Daily Inspiration Living in the City - Conrad Doucette

In Chapter 5 of 19 in his 2012 Capture Your Flag interview, musician Conrad Doucette answers "How Do You Make the Most of Living in the City?"  Doucette speaks to the daily interaction of coming into contact with artistic, creative and passionate people.  He shares what he enjoyed about getting out of the big city and traveling out of town to Woodstock, New York, where he found musical inspiration.  He realizes how he enjoys both city life and rural life but at his core the city life comes down to daily inspiration that can't be beat. 

Conrad Doucette is a Brooklyn musician and the drummer for Takka Takka, which released its 3rd studio album, AM Landscapes, in late 2012.  He has performed with Bob Weir of the Grateful Dead, The National, Alina Simone, and many other leading acts.  When not performing music, Doucette is the communications and brand director at music licensing and publishing startup Jingle Punks.  Doucette earned a BA in History from the University of Michigan.

Matt Ruby on Learning the Realities of Working in Comedy

In Chapter 7 of 19 in his 2012 Capture Your Flag interview, standup comedian Matt Ruby answers "How Are Your Comedy Career Aspirations Changing as You Gain Experience?"  As Ruby gains experience performing comedy, he gets more exposure to what life looks like working in comedy.  Experience allows him to look beyond the glamorized life of a working standup comedian.  He learns the costs and benefits of the standup lifestyle and begins finding new options - writing, directing, producing - that emerge as he builds experience. 

Matt Ruby is a standup comedian and comedy writer based in New York City.  He produces a video comic strip at Vooza.com, co-produces the weekly show "Hot Soup", co-hosts the monthly show "We're All Friends Here", and writes a comedy blog "Sandpaper Suit".  Ruby graduated from Northwestern University. 

Garren Katz on How to Talk About a Career Change Decision

In Chapter 3 of 15 in his 2012 Capture Your Flag interview, business and personal coach Garren Katz answers "How Did You Set Expectations With Others and Yourself Making a Career Change?"  Katz notes how he was uncertain how to talk about his experiences and intentions going through the process.  Over time, Katz gets more clear on his journey and goals and in turn is better able to answer questions about why he did what he did. 

Garren Katz is a business and personal coach based in State College, PA and advises his national client base on small business management, entrepreneurship, relationships, and personal finances.  He is also an active angel investor in several business ventures.  He earned his BA from Western Michigan University. 

Stacie Bloom: When to Step Back and Think About the Big Picture

In Chapter 8 of 18 in her 2012 Capture Your Flag interview, Neuroscience Institute Executive Director Stacie Grossman Bloom answers "When Are You at Your Best?"  Bloom notes how she benefits from taking a step back from the minutiae of daily live to get a strategic, big picture perspective and make decisions.  While she enjoys performing under pressure she notes the importance of gathering different insights to make the decision. She shares the experience of putting together the Neuroscience Institute for NYU Langone Medical Center. 

Stacie Grossman Bloom is Executive Director for the Neuroscience Institute at the NYU Langone Medical Center.  Previously, she was VP and Scientific Director at the New York Academy of Sciences (NYAS) and, before that, held editorial roles at the Journal of Clinical Investigation and Nature Medicine.  She earned her BA in chemistry and psychology from the University of Delaware, her PhD in Neurobiology and Cell Biology at Georgetown University and did post-doctoral training in Paul Greengard's Nobel Laboratory of Molecular & Cellular Neuroscience at Rockefeller University. 

Transcript: 

Erik Michielsen:  When are you at your best? 

Stacie Grossman Bloom:  I think I’m at my best when I’m under pressure. I think I’m at my best when I have the opportunity to think strategically and take a step back and look at the full picture. I think you know it’s very easy in any job to get very wrapped up in the day-to-day minutiae and all of the little details, it’s not so often that you have the opportunity to just take a deep breath, take a step back, assess the overall picture and make very strategic and important decisions. And I think those are the times when I’m at my best. 

Erik Michielsen:  How have you come to realize that over time? 

Stacie Grossman Bloom:  You know, I think when I started this job as executive director of the NYU Neuroscience Institute, there wasn’t a lot going on at the very, very beginning. We had to lay out all these plans and that was the time that I was thinking most big picture strategically, and then as it was rolling out we were hiring people, I was putting together the administrative infrastructure, we started recruiting the faculty and life became more about, you know, how do we on board this person? Where are the fire exits? You know, I have to go through this checklist for human resources and train all of these people? How do I get them on payroll? What are their scientific areas of interest? How do I transfer their grants over? And I realized, wow, I’m gonna get really wrapped up in these daily details, at least once a week, I need to stop, and think back at why are we here? What’s our vision? What’s our mission? How are we accomplishing it? What are the steps that we’re making? What are our major accomplishments? What are our goals? And allow myself the opportunity to think that way and give myself the time to work like that.

Using Design Passion to Make the World Better - Ross Floate

In Chapter 13 of 20 in his 2012 interview, branding and design strategist Ross Floate answers "What is the Source of Your Passion for Design?"  Floate defines design as more of a problem solving-based than an aesthetics-based discipline.  After establishing his career, Floate finds his work is less about the technical elements of design and more about problem solving as it relates to communication and process efficiency that creates .  Ross Floate is a principal at Melbourne, Australia-based Floate Design Partners.  Experienced in branding, design and both online and offline publishing, Floate and his team provide marketing services to clients seeking to better communicate business and culture goals via image, messaging, and story. He is a graduate of RMIT University.

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.

Jon Kolko on How to Turn a Collection of Ideas into a Book

In Chapter 7 of 21 in his 2012 Capture Your Flag interview, design educator Jon Kolko answers "How Do You Take Collections of Ideas and Turn them Into Books?"  Kolko shares both his practical and theoretical approaches.  Practically, he simply writes and takes notes consistently and finds the notes and writings progressively congeal into a theme that then may then become a book project which then goes into the standard editing process.  Theoretically,  Kolko finds he fights himself making the decision to green light a book project and finds it happens around the 35,000 or 40,000 word mark. 

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: How do you take collections of ideas and turn them into books?

Jon Kolko: The process is pretty simple. There's probably like a theoretical answer as well as a practical answer. The practical is a little easier but my process is typically to just write; to write with no directive, no outline, no goal in mind over a process of about nine months to a year, and I write when I'm at conferences, and I write when I'm in class, and I write when I'm on an airplane. The pro tip here is the more time you spend on an airplane, the more time you have to write. And so, there is sort of a weird relationship with being in extreme physical agony on an airplane, on an aircraft and being massively productive but whatever. And then at some point, the thoughts of all of these different conferences and conversations and writing start to congeal into a theme, and usually sort of in backwards looking. It's sort of like a retrospective. It makes sense, like of course it led to this book theme. But there's never any of that sort of central plan. I've set out to write a book about a certain topic like four or five times and I've never written that book. And so it's much more of an organic process. And then once that clicks and you're like, “Okay, cool. The next book is called Wicked Problems.” Then I deal with standard editing process and outline, here's the different points I want to hit and then revise it and tear it down and write it again, kind stuff. But before that point, it really is all over the place. I'm not even sure that I'm cognizant that I'm doing it when I'm doing it. And so, like on my laptop, I have all my nice little folders and stuff, then on my desktop I’ll have little notepad snippets of just random stuff, you know 500 words, 1,000 words. At some point it all starts to make sense. The tools for this suck. There's got to be a better way to structure that in a way that can start to draw the parallels between disparate ideas more closely. But anyway, that’s the practical way of how you set out and write a book. How I set out and write a book.

The theoretical way, there are points in the process where you're like, “I don’t know if I should write this book. I don’t know if I have this book inside of me.” I've had that over and over and over and it's right around 35,000 words usually, which is kind of weird. A book is 45 to 90,000 words depending on how big it is but right around 35,000 something kick in and you’re like… it's that same old voice, right? It's like you don’t what you're talking about or you're not good enough, or this book will never work, nobody wants to read this. You could squelch that voice, right? You can shut it up. It's weird how consistently that voice shows up and it ran right around at the same point in the process.

Jon Kolko on How an Editor Improves the Book Writing Process

In Chapter 8 of 21 in his 2012 Capture Your Flag interview, design educator Jon Kolko answers "How Did You Learn to Work More Closely with Editors to Refine Your Writing?"  Kolko, who has written three books, meets an editor, Ronni, working on a book with the publisher Oxford.  His editor helps carry his voice when telling his story about design and do so in a positive way. 

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: How did you learn to work more closely with editors to refine your writing?

Jon Kolko: So I have a great editor. I first encountered her.  Her name Ronnie and I first encountered her writing with Oxford. My second book was with Oxford and then I was like, “I'm never working with publishers again!” and the one piece of that process that I retained was hiring a professional editor. And so we were joking about this before. I submit my manuscript to Ronnie and it comes back and literally 50 percent of it is redlined out, like cut, cut, cut, cut, cut. 

In many ways, the first time I experienced that, I was extremely taken aback. It was like “Woah, wait a second, what's going on here?” But in fact, it turns out that having that sort of objective perspective is of huge importance. 

I don’t actually think I'm a writer. I think that I'm a fairly okay person at putting together a book. But I'm not a writer. I'm not a writer in a way that I think like somebody like Steven Johnson is a writer. But because I have I think a different story to tell about design and I'm an okay writer, there is something special that comes out of that but because of that, I think an editor plays a much stronger role in my process. 

Typically, an editor doesn’t give you a voice and they try not to take away your voice. I don’t think my editor gives me a voice or takes away my voice. But anything that she helps structure, what are overly argumentative reasonings into something that’s much more absorbable by someone who just isn’t in the mood to get in an argument. I feel as an academic, like I need to defend the things that I'm saying, and I think one of the big points I learned from an editor is these are your points. You don’t need to defend them. Yeah, you need an academic trail and sure you need to cite your sources but go into it assuming that your reader agrees with you rather than assuming your reader is there to disagree with you. And the book will be much more positive and strong and she’s exactly right.

Jon Kolko on How to Design Culturally Relevant Social Solutions

In Chapter 16 of 21 in his 2012 Capture Your Flag interview, design educator Jon Kolko answers "How Have You Learned More Effectively Across Cultures?"  Kolko notes how design work is culture-dependent.  He notes how impact-based design is local and often constrained by the cultural environment.  This often limits scalability yet allows students to better focus their solution design for the communities it will serve. 

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 have you learned to work more effectively across different cultures?

Jon Kolko: Design work is explicitly tied to culture and in a super nuanced way. So, a design solution that works in this particular culture may or not work in a different culture and I don’t necessarily mean country or geographic boundary. It can be culture as defined by style, as designed by fashion, anywhere there are shared values. And so, when you're dealing with design for impact, it's really, really local and micro-driven, which is directly at odds with most impact investing and a lot of the places where you will find big money like the Bill and Melinda Gates Foundation who are looking to fund scalable solutions, solutions that aren’t going to affect 500, or 1,000, or 10,000, or even 100,000 people, that are going to affect 10 million people, 100 million people, a billion people. And I don’t claim to know if that’s a good or a bad process for them. I don’t know anything about their inner workings but for where my students are, which is nowhere near that in terms of impact, their solutions can’t, by definition, can't scale outside of a certain locale without changing.

It's not to say they can't change, but it's not a cookie cutter approach and traditionally design has been all about cookie cutter approaches. That is what design for manufacturing is about. It's about taking a single part and mass producing it exactly the same a hundred million times with no defects, shipping it all over the world. You can see where that breaks down in a really, really obtuse and dumb way with adapters on PCs that the same PC, the manufacturer has to make six or seven different ends to plug the thing in, in different countries. That has nothing to do with culture, it has everything to with these Legacy electric grids but that’s the equivalent of how prepared designers are to deal with that issue. It's like that’s all they know. Well, we got to localize it by changing the language and by using a different cord. No, no, no, it's so much deeper than that. The homeless in Belo Horizonte and the homeless in Austin, it's a different world. And to say somehow, “Yeah, I conducted a thousand hours of research with homeless in Austin and therefore my solution transfers to the middle of Brazil,” is just ridiculous. And so, I don’t know how my design work has changed as a result of that but my philosophy toward it is certainly crystallized around this idea of local design decisions being okay, that we don’t have to design for scale en-mass right away.

Jon Kolko on Teaching Venture Capitalist Thinking to Creative Students

In Chapter 17 of 21 in his 2012 Capture Your Flag interview, design educator Jon Kolko answers "How Has Working at a Startup Incubator Taught You to Better Teach Entrepreneurship?"  Kolko shares how his experience taught him the language of business and entrepreneurship and how to talk about products and services from a venture capitalist perspective.  For example, Kolko notes venture capitalists look not only at how a product might sell, but also the product intellectual property value. 

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 has working at a startup incubator taught you to better teach entrepreneurship?

Jon Kolko: It's definitely led me to understand the vocabulary around VCs and financing and how that game works around funding. It is a game and those involved in it will actually gleefully describe it is a game. And so, I think working at sort of the heart of that helps me understand both what that mentality is like and how to leverage it if you want to or how to completely avoid it if you don’t like it.

It is literally a different language and I don’t just mean in terms of vocabulary and jargon. Yeah, there's a ton of jargon and that takes a little getting used to but it's also just a very different way of talking about products and services.

And I’ll give you a very quick example. When a designer creates something new, irrespective of social entrepreneurship or anything else, they think of the value of that thing to a user. And typically, a good VC, will when they look at something new, will think of the IP value of that beyond the simple investment. Meaning yeah, that’s great. I obviously have to get my 10X return over three to five years. And then how can we continue to leverage the intellectual property that’s inherent in this invention well beyond me actually owning -- you know, having a full stake in this company because that will allow me to sort of tweak up that valuation. The notion of an invention having monetary value outside of its sales price and outside of the value for a user is 100 percent missing in the world of design, for better or worse, and I don’t really care to argue the value or non-value of IP right now. But it's just that it doesn’t cross any designer’s mind I've ever worked with in my life. And it's like the first thing that most good VCs will think about.

And so as an example then, if you're trying to teach a student how to present their work during a pitch, one of the things they need to understand is that the person looking at their thing is not thinking about how much is it going to sell for on the shelves of Best Buy, right? There's this second market of IP that they're considering which is totally in a third plane. That designers are like, “I don’t even know what words you're saying.” And that’s just an example. There’s tons of those. There’s tons of different ways of thinking about stuff.

Ask a designer what derivatives trading means. And it's not just that they don’t know because they're inexperienced. They don’t know because their brain doesn’t work that way. It's the same way when you ask somebody who’s in financial services to draw a teapot. They’ll say they can't but it's literally like their brain will not allow them yet to draw that teapot. And I think the closer, the sooner students realize that, the sooner they can decide if they want to overcome that hump or not.