[quote style=”boxed”]I break things into short-term, medium-term, and long-term projects. I make sure the short-term issues are covered and allocated, spend some time managing medium-term projects, and spend a little time on long-term projects. Essentially, I work with our startups to get traction, plan long-term events, and raise capital. I like to automate routine processes so they can easily scale, so I spend time each week working on automation. I also review monthly goals each day to make sure I’m on track.[/quote]
Michael Goldstein is a serial entrepreneur with 15 years experience focused on e-commerce, online content and subscription businesses. Michael has founded five businesses and sold three, including DealPal to XL Marketing in 2010 and Magazine-of-the-Month to Magazines.com in 2004.
Michael’s passion is for growing start-ups and he has been involved with multiple start-up businesses as an advisor & mentor. Start-up involvement includes:
OrderGroove, a business idea Michael worked with a recent GW graduate to formulate and launch. OrderGroove is experiencing rapid growth and recently raised its second round of funding.
NextGame, a mobile app that enables users to find meet-up sporting events and serves as a centralized database of all types of sporting events.
What are you working on right now?
We are planning a large event in Washington, D.C., to connect big companies with startups. SwitchPitch is a reverse pitch event where large companies pitch tech needs to an audience of startups. When we looked at the D.C. ecosystem, we saw big companies with money to spend looking for innovation, but they didn’t have meaningful connections to the growing startup community. We felt there was an opportunity to connect these two groups.
The large companies benefit by directly meeting innovative startups ready to work on projects, and the startups benefit by efficiently networking with a large group of business development contacts at a single event. Startups are able to forge relationships with companies that will be impressive to future clients and investors. Hopefully, the relationships will even lead to acquisitions.
Where did the idea for Exhilarator (formerly Endeavor DC) come from?
I’ve been an entrepreneur since I was a little kid, and I have both grown and sold my own businesses. Five years ago, I met a very smart young entrepreneur while guest lecturing at George Washington University. We kept in touch, and when Greg decided he wanted to launch his own business, we brainstormed ideas and came up with a subscription management business for ecommerce merchants. I incubated the business and helped get him started.
Greg moved the company, OrderGroove, to New York and raised several rounds of funding — most recently, a $6.7 million B round from top-tier investors. The business model is phenomenal, and Greg is amazing with strategy and execution. The experience of mentoring him, working closely with him throughout the growth of his company, and staying involved today as an advisor has been incredibly positive and rewarding. I started Exhilarator to help make more OrderGrooves.
What does your typical day look like?
I break things into short-term, medium-term, and long-term projects. I make sure the short-term issues are covered and allocated, spend some time managing medium-term projects, and spend a little time on long-term projects. Essentially, I work with our startups to get traction, plan long-term events, and raise capital. I like to automate routine processes so they can easily scale, so I spend time each week working on automation. I also review monthly goals each day to make sure I’m on track.
How do you bring ideas to life?
First, we begin with the end in mind: What does this look like 18 months out? What about three years out? Once the long-term vision is established, we work backwards. Where do we need to be in six months? Then, where do we need to be one year from now? That takes us back to the immediate plan of getting things going in a direction that will take us toward our long-term goals.
We spend a lot of time using whiteboards and online tools to map out the details of ideas. We use wireframes and mockups to get a feel for how it will look. At that point, we start bringing in other resources for architecture, development, and design. Establishing the vision we want to convey to others is critical, and distilling that idea to a few sentences or words is even more so. We stay laser-focused on the core value propositions; we’re constantly evaluating value creation.
One way I evaluate value creation is by thinking about ideal customers and their commitment to getting a new product or service. Would the ideal customer wait in line for five minutes if that’s what it took to get the product or service? If downloading an app took five minutes, would customers stick it out or abort?
What’s one trend that really excites you?
Organizing and bringing new pools of data online is exciting for me. Specifically, I’m interested in making sense of things that haven’t been available before, such as government data, and combining that data with existing data in new ways — it creates a big opportunity. People use the term “big data” a lot, and this idea is partially that. However, rather than just capturing a lot of data about things that are happening around us, I am interested in unlocking data that exists but isn’t available.
What was the worst job you ever had, and what did you learn from it?
I had a job in college handling billing collections from unpaid customers for a customized news service delivered via fax. I would call customers and explain to them why they owed us money — we’d delivered the service. They would say they never read the faxes and shouldn’t have to pay. I learned that value creation is in the eyes of the beholder. If the value is there, people will happily pay. If there is no perceived value, people get upset.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
I love the concept that Steve Jobs popularized in his Stanford commencement speech address: “Stay hungry. Stay foolish.“Stay hungry. Stay foolish.”” To me, these two qualities or desires are at odds. Foolishness is doing what feels good and what you inherently know you should be doing — but you can’t justify why. Hunger is what you need to do to survive. I find the juxtaposition between these seemingly-at-odds desires fascinating.
Many young entrepreneurs are heavy on the foolishness — in a good, world-changing way, but they are also light on the hunger. However, once people get established, have kids, etc., it is easy to become hungry and lose your foolishness. I try to stay balanced between the two and strongly encourage others to do the same.
What is one business idea that you’re willing to give away to our readers?
Develop an in-venue app that could monetize unused seats at sporting events and concerts by letting people upgrade to better seats once they’re seated — I’d call it Move on Down. People trying to sell tickets on StubHub or other online marketplaces would have the option to put their unsold seats into a pool of in-venue, upgradable seats. The app would take a lot of deals from venue owners and ticket holders, but it’s a doable and amazing idea. Some have tried it, but no one has done it successfully.
Tell us a secret.
Finding a few people to serve as mentors or advisors who make you feel like anything is possible will change your perspective on what you can accomplish.
What are your three favorite online tools and what do you love about them?
MindMeister: A mind-mapping app for web and mobile that lets you create cloud-based mind maps and access them from any device.
LeanLaunchLab: A great business canvas creation tool that allows for hypothesis testing and quick iterations for fast-growing startups.
Yesware: A great Gmail plugin for sales people, this lets you track email opens and easily create template emails for routine correspondence.
What is the one book that you recommend our community should read and why?
Walter Isaacson’s “Steve Jobs” is a must-read — even if you think you know all the stories.
What’s on your playlist?
I’m listening to Beastie Boys and electronic dance music.
If you weren’t working on Exhilarator, what would you be doing?
I would be rolling out another startup or taking SwitchPitch to other cities and verticals.
Three people we should follow on Twitter and why?
Steve Case — He’s a business legend, and he’s funny.
MIT Tech Review — This offers an interesting perspective on tech from the mecca of technology.
Fred Wilson —This guy knows scalable tech and thinks big.
When was the last time you laughed out loud? What caused it?
I laugh out loud a lot. Today, I had a phone call scheduled with a guy who had a very unfortunate first name that’s also an inappropriate word in an office environment. In our open office, I had to say, “Hey, Dush, great talking to you!”
Who is your hero?
I’m not sure I have heroes. There are people I admire. My father made me believe that anything is possible. I have a few mentors who have been incredibly loyal to me and look out for my best interests. I suppose that Steve Jobs is really the closest thing to my hero.
Tell me about a time you failed and what did you learn?
When my last company, DealPal, was sold to XL Marketing, I transitioned the business and then wanted to launch a new startup with XL Marketing. I pitched the concept of a national daily deal site with ecommerce-related deals every day. The site, CountOff, launched in mid-2011, but the customer acquisition costs were prohibitively expensive. It was clear that the business could not exist as a consumer-facing daily deal site, but we were good at sourcing the deals using our ecommerce relationships.
We decided to pivot the business and put together a syndicate of other daily deal sites; we listed our offers, and other sites could pick up the offers and sell them. That angle worked, and we were able to source a lot of deals. The lesson learned: Leverage your assets and use them to create value.
What would you have done differently in your personal life?
There have been some business decisions that impacted my personal life in big ways. A lawsuit was an incredibly negative force on our family and could have either been avoided or settled quickly — had I not let ego get in the way. I knew I was right and wouldn’t back down, even though the impact on my family was significant. Unfortunately, the expression “When you’ve got them by the balls, their hearts and minds will follow” applied to our hearts and minds.