Insights From The Great Lakes

This post originally appeared in TECH Cocktail.

I attended the Great Lakes Entrepreneur Bash which was a panel event in Chicago that brought together successful entrepreneurs highlighted in Bob Jordan’s new book How They Did It: Billion Dollar Insights from the Heart of America. The stellar panelists included:

  • Bill Deville: Co-founder & CEO of Health Carousel, previously co-founder Health Personnel Options
  • Jim Dolan: CEO of The Dolan Company, previously was EVP of the Jordan Group Inc.
  • Tim Krauskopf: Principal at Round Lake Designs LLC, co-founder of Spyglass whose version of Mosaic became Microsoft IE
  • Chris Moffitt: Co-founded Rubicon Technology and previously co-founded Diamond Management and Technology Consultants and Technology Solutions Company
  • Vince Pettinelli: Founder of PeopleServe which was acquired by ResCare
  • Michael Polsky: Founder & CEO of Invenergy, previously founder of SkyGen Energy
  • Mark Tebbe: Co-founder & lead director of, previously founder of Lante Corporation
  • Robert Jordan: Author and owner of two companies, RedFlash and interimCEOinterimCFO

The vision for the event was to provide the audience with the “secret sauce” of going from a solo startup founder to thousands of employees and millions in profit. As only an hour-long event, it couldn’t fully deliver on its promise, but there were some fascinating peeks into the Chicago-land tech scene and insights from its successful entrepreneurs.

1. The only way to do it is to do it your own way. From exit “numbers” to building for the long run, recurring revenue to living for the next deal and public vs. private companies, every panelist had their own unique take on the different entrepreneurial angles. Michael Polsky summed it up best when he said, “Everybody will do it their own way, you really can’t do it any other way.”

2. Love what you do, be good at it and have fun with it. If not, get out quickly. The passion and conviction leapt out from every single entrepreneur on stage. It was clear as daylight that they loved what they did. And if they weren’t having fun they didn’t hesitate to sell like Mark Tebbe with Lante Corporation. Mark then went on to co-founder and stressed the importance of “doing what’s important to you and doing it well.” Jim Dolan waxed poetic about “the magic of inventing a future that’s more fun than yesterday.”

3. The only thing you should count on is persistence. The media generally paints out a tidy story for successful entrepreneurs that show them headed to great things the moment they start out on their own. The reality couldn’t be further away from it. More than one panelist talked about their weakest moments – Jim Dolan mentioned going into bankruptcy twice and Mark Tebbe jokingly said that he still hadn’t recovered from financial mishaps. The only thing they all agreed on unanimously was resilience. Chris Moffitt said “when there’s a tragedy, stand up, dust yourself and move on.” And move on they eventually did to bigger and brighter things. Jim Dolan hearteningly pointed out that if you do pick yourself back up, you’ll find that the people who invested in you will be willing to back you again.

4. Entrepreneurship requires a higher risk profile. The key message that all the panelists hammered home was that if you’re brave, courageous and willing to take chances, albeit calculated, then the world is yours for the taking. Chris Moffitt said that entrepreneurs should have the appetite to shake up the business even if and especially if the opportunity was within a billion dollar market. He also mentioned that things may not work out exactly how you imagine but if you’re willing to take a chance, then you can find a way to make it happen.

5. Entrepreneurs love it so much they end up being serial entrepreneurs. Bob Jordan, who moderated asked what the panelists did when they had financial market fluctuations and Chris Moffit readily quipped, “Start another company.” The fun of making a startup work seems so addictive that all the speakers went on to found multiple companies.

Other fun and insightful quotes from the event include:

  • “Making a bad sale is like building a dream home, taking your time to decorate it and then selling it. The buyer moves in and says you can keep living there but asks you to move to the basement. Then they proceed to undo all the things that made the house special in the first place.” Chris Moffitt
  • “If you celebrate your ignorance, you’ll surround yourself with people who are smarter than you are.” Vince Pettinelli
  • “If you can find a way to make money while you & your team are sleeping, that’s a great day!” Mark Tebbe
  • “Dissect your mistakes, analyze them but definitely don’t bury them.” Jim Dolan
  • “Do I wish my company had sold for more? Yeah, but I also wish I was taller and many other things.” Mark Tebbe

10 Insights From SocialDevCamp Chicago

This post originally appeared in TECH Cocktail.

SocialDevCamp Chicago took place this past weekend and had so many poignant moments and key takeaways that it took a while to digest. From high profile keynotes by representatives from GrouponGoogleCheezburger Network, talks on the business and technology sides of the social web and lively, moderated unconference discussions to a weekend long hackathon – the event certainly had something for everyone. This post hones in on the most interesting takeaways for entrepreneurs, developers and web enthusiasts. Lists of trends or tips were very popular with the presenters and so in true SocialDevCamp style, here my top 10 insights from the conference:

  1. Being social is not an add-on but mission-critical. When the conference title has “social” in it, you know it’s a pretty important theme. Groupon CEO, Andrew Mason said that the company’s unparalleled growth was merely a product of its times where the social nature of the web makes companies grow faster than ever before. Social proofing with one’s network serves to test concepts and ideas and highlight for us what’s important. The “curated by friends” model is taking word-of-mouth to a whole different level. Community is breathing life into any web presence. And so whether it is augmented reality, having online-offline tie-ins, crowdsourcing deals or enriching the experiences for brand advocates, social and its myriad online manifestations are hot, hot, hot.
  2. Environment has environmentalists, women have feminists & so the web needs webinists. Chris Messina, the Open Web advocate at Google made a thoroughly entertaining and compelling argument for maintaining the integrity of the social web as it is today. The central tenets of his speech were what he termed “POP computing” and generativity, inspired by Josh Zitterman’sThe Future of the Internet & How to Stop it. The death of URLs, lean-back devices where freedom is traded in for usability, app stores with a curated non-transparent model and instant personalization are some of the things that comprise the “POP computing” phenomenon – the move to a clean and frighteningly sterile Internet. Generativity includes being flexible, adaptable, providing easy access and making it easily transferable especially to non-experts with the goal being to federate social ties more effectively. It’s easy to think of the future of the Internet as far removed from our own purview. But Messina left the audience with the powerful message that maintaining freedom, choice and innovation on an open web is ultimately our responsibility either as developers using OpenID or OAuth technologies or laymen taking the time to understand the nuances of net neutrality,
  3. Go work for Groupon – they’re funny, smart and apparently have some cash to spare. It was quite the Groupon love fest at SDC with Mason’s lunch keynote and the product team shedding some light on the Groupon way of development. Mason quipped that Groupon is representative of consumers and hence can “talk to ourselves in ways that doesn’t make us want to throw up.” When asked about his company culture, he said that he “doesn’t want to be the kind of company with passive aggressive signs on the refrigerator asking people to get their moldy stuff out” and was not afraid to “sound the stupidest…and [hence] more interesting.” For engineers, joining a company like Groupon rather than starting something on their own might be a great option, Mason said, because they probably wouldn’t see problems of a huge scale in a startup. So if you’re a polyglot excited about solving problems, being around smart people and singing to loyal customers, look up Groupon…they want you.
  4. Please KISS (Keep It Simple Stupid). Simplicity is elegant and effective and that was repeated through multiple sessions. Mason said that you really just have one and a half seconds for your users to get the value proposition and his product team, Suneel Gupta and Shinji Kuwayama echoed the same sentiment. Ben Huh of I Can Has Cheezburger? fame pointed out that while human nature has a tendency to admire complexity it rewards simplicity and that admiration and actual revenue come from two very different places. He asked the audience to focus only on what users would do if they had 40 seconds on your site.
  5. Mobile does not equate to being an extension of the web. Computer usage is plateauing while our mobile phones continue to become intricately fused into our lives, changing social behavior one habit at a time. While the mobile industry might be rewriting social norms, make sure your mobile product is not explicitly changing behaviors. The mobile platform is definitely its own entity and it makes no sense to think of it as a mere extension or adaptation of the online experience. Also, as an added benefit, thinking of a mobile experience/app forces you to prioritize features.
  6. Don’t quit playing games with your users’ hearts. Game mechanics are definitely here to stay. Users like their achievements, badges, awards earned for engaging with your product/service and the more gaming elements they interact with, the more addictive it becomes. An obvious big picture trend is the tie-in of gaming with location and loyalty programs. So, for the health of your product, don’t quit playing games.
  7. Enable all the incurable builders. The 36-hour long weekend hackathon produced some great work but even beyond the developers that participated in the challenge, the atmosphere was one aimed at enabling developers and entrepreneurs. Code sprints and other challenges initially attracted hackers by dangling prizes, but towards the end, people got a rush from being part of a team that produced something. Channeling this could benefit less tech-savvy, non-profits and help increase the technical pool as well.
  8. Features don’t cut it but experiences sure do. The Groupon product guys stressed the importance of honing in on the customer experience – keep asking what customers want, need and feel when they use your product. Mason quoted a study that said people who focus on experiences rather than products have happier lives. Long-term success stems from an emotional attachment being created with your user through engaging experiences.
  9. Move over lean, MPH (Mr. Potato Head) methodology is here. Ben Huh uses the MPH strategy when growing the Cheezburger network which has a portfolio of sites like LOL Cats and Fail Blog among others. If a significant component of your site/product is lost, it will be ugly but no one dies. Some of the key tenets of the funny yet brilliant MPH philosophy:
    • Partner with businesses that have proven structural independence like Gmail or WordPress.
    • Make it easy to try before you buy and to get in and, easier still, to get out. If users can’t get out of something, they won’t get into it in the first place.
    • Prove before you spend anything.
    • If you spend time building something, it should be a competitive advantage. Outsource all the irrelevant stuff.
    • Ask if you can you plug in/out for a better, cheaper or faster solution.
    • Minimize the cost of failure to almost nothing because then risk becomes palatable and that ultimately ups the chances of success.
  10. Oh ye of little faith, the Chicago tech scene is definitely alive and growing. Having interesting (grown-up) startups like 37signals and Groupon in the area definitely helps create a talent pool of people who can then deploy their own business and tech prowess in startups thus fuelling the entrepreneurial ecosystem like in the Valley. An interesting upcoming startup is Nowspots, a real-time advertising technology provider for local publishers created by the Brad Flora (Windy Citizen) who won the 2010 Knight News Challenge.

7 Reasons to Start a Company While in School

Rockstar career trajectories aren’t about playing it safe. Luckily if you’re in school, starting a business might be the smartest risk-free career move you could make.

While in graduate school at Northwestern, I was a student by day and the co-founder of a social gift recommendation startup,Present Bee by night.

Drawing from my experiences, here are the top 7 reasons for starting a company while you’re still in school:

  1. Access to important and influential people. Colleges are a hotbed of potential advisors. Professors in technology, marketing, law, communication, accounting and management collectively hold an incredible wealth of knowledge. More importantly, they actually enjoy helping out motivated students wanting to start companies. Not to mention that it is part of the reason they went into academia in the first place! You’ll constantly be amazed at how willing they are to tap into their expertise and deep networks to help put you and your startup on the right path.
  2. Resources, resources, resources. Free WiFi, superior computer labs, heavily discounted student software, copy and fax machines, scanners, printers, meeting rooms, conference facilities, amazing library material that you’ll have to give up your first born to afford when you leave school…need I say more? Universities are some of the most technologically connected places and almost any resource you’d need to start a business is available right in front of you at a fraction of what it costs out in the real world. You’re paying for these resources in tuition and student fees anyway, so why not take full advantage of it?
  3. Huge market research/customer/employee base you can lure with pizza. Your friends, friends of friends and even their friends all want to help you. Pick their brains on the products and services they like, get them to test your product, give you invaluable feedback and even get them to become loyal customers. Sometimes all you’d have to offer them in return is free pizza or muffins. Also, if you’re looking for help with your startup, there’s no better place to be than on a college campus. Colleges are filled with bright young people who are eager to learn & gain new experiences through [poorly-paid or mostly unpaid] internships that help them fill their resume. Look around you in your classes -– your co-founder or first employee might be sitting right next to you.
  4. Student loans are not as expensive as having a family and a mortgage. Now is the time to take financial risks with potentially large payoffs. Even if your startup fails, which it probably will, you’re young and you can move on more quickly from being broke than when you have to support kids, a spouse and recurring payments on your house. Plus ironically, having a track record of building something and managing a team in your own startup makes you more attractive to other employers should you decide not to go the startup route.
  5. Time. School has flexible timing -– you can pick your class schedule of choice every semester/quarter. You can stack all classes in two days or have them all in the evening if you want, which would then give you a lot of free time to start and run a business. Going out into the real world after graduation means your time suddenly becomes very restricted. You’re expected to spend 40 hours (or more in most cases) rooted in your office seat and will only be able to work on your startup in your spare time, which may not be much.
  6. Don’t let schooling interfere with your education. Yes, Mark Twain said that and you should definitely listen to him. Schools teach you a lot of interesting things but there’s also a host of topics that they don’t even begin to cover. Startups can definitely help you fill that gap. Some valuable lessons I’ve learned through Startup 101 –- how to get people (other than your mother) to use your product, how to work 20 hour days with people in one room and not kill each other, how to build a realistic financial model that isn’t limited to looking pretty in Excel and many other gems. Also, if you’re unsure whether you’d like to run your own company after graduation, the best way to find out is to start one while you’re in school.
  7. Entrepreneurship is sexy. When you’re asked to introduce yourself, the line “I started a company” never gets old. Enough said.

To close, let me quote Marc Andreessen, the founder of Netscape, investor, startup coach and all-round extraordinaire:

“Start your own company. If your startup fails, try another one. If that one fails, get back into a high-growth company to reset your resume and get more skills and experiences. Then start another company. Repeat as necessary until you change the world.”

Also check out a classic talk from Paul Graham, the founder of Y Combinator, on Why to Not Not Start a Startup. I’d like to hear from you student (and non-student) entrepreneurs out there –- what’s the most interesting reason you’ve started a company?