The Captain Of You

I feel like I’m a passenger of my own life.

I’m not afraid of going on welfare. I’m afraid of being ordinary.

As I heard him say the things I saw my life flash before my eyes. I recalled the decisions I’ve made, the places I’ve traveled to, the friendships I’ve made, the speeches I’ve heard.

But most importantly…

The things I’ve done.

Right or wrong, good or bad life is all about the choices we make and the choices we follow through with.

It’s about doing.

It’s about being the driver and captain of our own life and not being a passenger that’s merely along for the ride.

The irony here is that what holds us back to start, becomes the thing that drives us forward in the end. It’s what rips us out of apathy and tells us that something is wrong.

That thing is called fear.

Being afraid to fail leads us down a path of passiveness. And as we walk down that path we begin to realize just how bleak the path is.

Most of us have seen it before.

It’s a straight line and the roads are smooth from all of those that went before. The speed limit signs of society tell you to that you’re a million miles and decades away from your goal.

Your goal.

You forgot what that was because you were busy thinking about the next pit stop as you stare at the clock of life counting down the seconds and days until you reach a checkpoint.

Marriage. Kids. Buying a house. Paying off a mortgage. College tuition. Switching jobs.

Each pit stop you look back and wonder if you got on the right path.

Each pit stop you look forward and wonder if you can get off.

Where would that exit take me? Am I even capable of getting off?

You realize that the other path, the path of uncertainty and maybe even failure, is a lot less scary than this path of passiveness of ordinary.

You wonder what if you just got on that windy, uncertain road to begin with? And then regret starts to settle in. What if I did those things I was afraid of doing? What if I didn’t settle and do what was expected of me? What if I followed my dreams and put myself out of my comfort zone?

I read a quote somewhere once that said most people overestimate the cost of doing something and underestimate the cost of doing nothing.

Truth.

That person is a smart guy.

And right or wrong, the smartest thing we can do as people is to live life to the fullest. To be the captains of our own lives and to embrace fear head on.

The best thing we can do is to do.

Something..

Something that is extraordinary, scary and defines who you are and who you were meant to be.

It’s not too late.

It’s never too late to look fear head on and say it’s my turn to drive. It’s my time and I got it from here.

And in that moment, you realize you can do anything and that you are in control. You’re the driver again and the captain of your own life.

The captain of you.

How These Founders Built A $1 Million+ Business And Acquired A Competitor All While Bootstrapped

This post originally appeared on Forbes.com.

These days, it seems rare to meet entrepreneurs who have opted to bypass the route of raising venture capital in favor of a building a business that sustains itself through revenue. Josh Goldstein and Chris Muir, cofounders of an NYC-based hiring startup that’s quietly amassed a customer list with some of the best-known technology companies in New York and San Francisco, including companies like Kickstarter, Warby Parker, and Etsy, have done just that. Underdog.io took to its blog today to announce that it had acquired Sourcing.io, another company in the recruiting space, for an undisclosed sum.

I had the chance to catch up with Josh and Chris about bootstrapping their business, financing an acquisition out of revenue, and how they see themselves within a broader recruiting industry that’s rife with venture dollars.

Dan Reich: How did Underdog.io come about?

Josh Goldstein and Chris Muir: We started Underdog.io as a side project back in April 2014. At the time we were working on a different business – enterprise software for real estate property managers – but we weren’t close to making any money with it and started brainstorming some other products that would help us pay the bills. Underdog.io was one of those ideas, and probably the one that we felt the strongest about. After getting some early traction with it, we decided to go all in.

Reich: You both have experience at venture-backed startups. Did you guys plan to build a bootstrapped business?

Goldstein and Muir: We’ve never set any hard and fast rules about fundraising. The only rule that we had when we started Underdog.io  – and this was probably a result of both of us having worked at startups with no revenue – was to build a product that people would pay for on day 1. This was super important to us…much more important than raising tons of money or getting a write-up in TechCrunch.

Reich: Where did the idea to acquire Sourcing.io come from?

Goldstein and Muir: Both of us have been big fans of Alex MacCaw (the founder of Sourcing.io) for a while, in particular his blog and his writing about the state of recruiting in SF. As part of building Underdog.io, we tried out a number of sourcing products, including Sourcing.io. We loved the interface and some of the social and team features that Alex was building. Fast forward a few months and we jumped at the chance to meet with Alex when we found out that he was looking to move on and focus on another business.

Reich: Now that you’ve made this acquisition, what are your plans?

Goldstein and Muir: We’ve got lots of work to do to integrate our two products, onboard some new customers, and make sure that our existing customers understand where we’re headed. After that, it will be business as usual for us, which means staying focused on giving candidates the best experience possible and giving companies a cheaper and easier way to hire great teammates. The recruiting technology space is full of companies with big war chests and even bigger financial expectations. One advantage of bootstrapping is being able to stay focused on what matters to you, which is a luxury that we’ll take advantage of for as long as possible.

Reich: What’s one piece of advice that you’d give others that are looking to bootstrap a business?

Goldstein and Muir: Prepare yourself for a slow grind. Bootstrapping is neither harder nor easier than raising money, but it’s definitely slower. Almost every roadmap you have – from product development to hiring – will be extended because you have fewer resources than you need and, more than likely, fewer resources than other companies in your industry. Stay focused and try to use that slowness to your advantage in some way.

When R2D2 and TARS Show Up For Work – My New Company, Troops

This post originally appeared on Forbes.com.

I’ve been thinking about R2D2 a lot lately and it’s not because I’m a nerd or a big Star Wars fans. Although on some days I’m probably both. I’ve also been thinking about the other sci-fi movie robots out there like TARS from Interstellar, Samantha from HER, or even Arnold from The Terminator.

I think Jeff Bezos and Elon Musk have been thinking a lot about this, too.

Once upon a time artificially intelligent machines, talking robots and self driving cars were just some figments of imagination but now we have Siri, Amazon Echo and Tesla’s driverless cars.

And these are just the pre-school version of what is yet to come. You can be sure these technology juggernauts like Apple, Facebook, Tesla and Google are cooking up some next level, world changing solutions. I mean, Google just created an entire holding company called Alphabet to do precisely that.

Our society has finally crossed a threshold with technology, and there is a shift underway.

Invisible apps, zero UI, artificial intelligence, messaging-as-software. These are all phrases I’ve heard over the past few months that are meant to convey that shift which is: We’re at a moment in time where software can adapt to humans whereas before humans were the ones adapting to software.

Microsoft calls it “Productivity Future Vision.” I call it, “just getting stuff done.”

The software, computing power, hardware, interoperability of platforms, and APIs are all there for this shift to finally happen and for highly complex systems to be built and deployed at scale.

I saw a tweet the other day that said API’s were the unsung hero of technology. There is certainly some truth to that. They allow us to move beyond stand alone solutions to a world where solutions can work with other another.

And to date, those stand alone solutions, at least in terms of software have mostly been about drop down menus, check boxes, field and forms, and some mediocre UI and UX. It’s been about making screens look pretty. Making buttons click so that you can turn to yet another pretty page.

But the next 10 years will be about machine learning, artificial intelligence, natural language processing and technology that is contextually aware to human beings and their preferences. It will happen through interfaces that are intuitive and commonplace to human behavior.

Ben Evans says messaging is the software and not the other way around.

I agree.

I’m personally interested to see how this plays out in an enterprise environment and so I recently started a company with some amazing people to put these thoughts to paper and ideas to bits and code.

Someone once told me that we spend a third of our lives sleeping, a third working and a third watching TV. And it seems like an incredible time to try to make that “working third” a little better for everyone and to do so with entirely new engineering and software development concepts.

And the new company?

It’s called Troops.

How These 20-Year-Olds Raised $13M And Built A Massive Food Tech Company

This post originally appeared on Forbes.com

Being a young, first time entrepreneur is hard. Without a stunning success story or years of applicable experience, a new founder can face significant challenges starting and growing a company. A study by the University of California indicated that the average venture backed founder is 38 years old with 16 years of work experience. That’s quite a gap when it seems today that every new startup founder is in their early 20s.

What challenges differentiate a veteran entrepreneur and a newcomer’s experiences? What are strategies a first time business owner can employ to maximize the chances of success?

Eat Street's Office in Madison, WI
Eat Street’s Office in Madison, WI

Eric Martell started EatStreet, the largest independent food ordering company in the United States, when he was 20 years old with two classmates at the University of Wisconsin. EatStreet has raised $13 million and powers the online ordering of 15,000 restaurants nationwide. The startup, founded in 2010, exists in a cohort of foodtech and delivery companies that have some impressive deal flow: Instacart raised $220 million at a $1 billion valuation, Postmates has raised $138 million.

I recently chatted with Eric about starting a business in college and about the explosive growth of the food and delivery tech sectors.

Dan Reich: Speak to the challenges of starting a company at 20 years old.

Eric Martell: Early on, and to this day, we’ve had to convince others to take a risk on us, because we’re young and don’t have any pre-EatStreet experience running a tech company. In 2010, we had to convince the restaurants to take a chance on us. Matt was walking into every restaurant in Madison, WI with a simple pitch that our service would bring the restaurants more orders from new diners. Restaurants were wary of the entire idea, because if we took an order online and didn’t properly ensure that the restaurant received the order and could fulfill it, the diners would blame the restaurant for the poor experience. Additionally, we accepted payments online, which meant that we had to pay the restaurant every week, so they had to trust us with their money. Matt looked young for a 20 year old, and he heard more than once that the restaurant “just didn’t feel comfortable doing business with a kid.” Matt was able to sign up five restaurants when we launched February 1, 2010. With some results under our belt, we were able to expand that list to over 100 Madison restaurants within a year.

Additionally, in order to process online payments, we needed the trust of a credit card processor. We applied for six processors before getting approved… there was a lot of inherent risk to accepting online payments and transferring out the payments to restaurants on a weekly basis. It took over two months of searching before someone took the risk on us.

If it weren’t for those five restaurants and the credit card processor taking a risk on us, EatStreet would not exist.

Dan Reich: Do you still face challenges similar to these?

Eric Martell:  Although the nature of the challenges has changed over the years, we still face obstacles from being first time entrepreneurs. We’ve raised over $13 million from venture capitalists, and every single one of them has taken a risk in betting on our drive. We also form strategic partnerships with companies like Yelp, Google, Single Platform, and Hotel Communications Network. These businesses need justification to take risks on a company like ours. I’m glad to say that we’ve always been able to put up results, and the company is the strongest it’s ever been.

Dan Reich:  Do you think the current trajectory of food and delivery business funding and acquisitions will continue?

Eric Martell: We stand by what we’re seeing. GrubHub IPO’d a little over a year ago, and has consistently held its value as a multibillion dollar company. Over in Europe, DeliveryHero has raised over $1.5 billion, and Just-Eat also had a very strong IPO. With even Amazon and Uber eyeing the food delivery space, we’re happy to be where we are, with strong relationships with thousands of restaurants.

Dan Reich: Do you have any advice for first time entrepreneurs facing challenges regarding their experience levels?

Eric Martell: Persistence and results. Matt went to over 100 restaurants and only signed up five for our business’ launch. We could have called it quits after five credit card processor rejections. Our investment pitch historically has had less than a fifty percent success rate. Accept the failure as inevitable, and push forward. We’ve had restaurants that initially refused to sign up with us tell us today that when they finally did sign up with us, the additional orders we drove saved their business from going under.

Results might not always be present, but they speak louder than the best sales pitch. Focus on the aspects of your business you have control over, and grow like crazy. We didn’t raise a dollar until we had over $1 million in food sales, and that first million was the product of thousands of hours of promotion and hard work. It’s much easier to convince someone to believe in your vision if you have a track record of growth and hard work to back it up.

My Unhappy Customer Wanted to Kill Me

This post originally appeared on Forbes.com

When I was in high school, I learned two important lessons about business and life.

First, if it’s too good to be true it probably is and second, know who your business partners are. Unfortunately, it was only after receiving death threats from an anonymous Russian, that I came to understand these valuable principles.

About five months earlier my friend and I were sitting in the back room of history class. As a 10th grader, the back room is prime time real estate. It’s where you can get most of your note passing, whispering, and sleeping done. We had been talking about different ways we can make money. This was a hot topic because just a few weeks earlier I was making some spare change by selling bouncy balls to my friends. I’d buy them wholesale on eBayand then sell them for $0.25 to $1.00 per ball depending on the size and color. It was my first lesson in wholesale economics and my friend took notice.

bouncyballs

I sold these like hot cakes in high school.

The teacher continued on with the lesson and my friend leaned over, “I know a guy that sells urban clothing at wholesale prices. We should take a drive down there and see what kind of clothes we can buy. We could even resell them to our friends.” There wasn’t really much to think about. I already knew the answer. “Done” I said. “Let’s go after school.” I should of however asked, “how do you know this guy?” I would learn later that the wholesaler was involved with scams before.

Failure #1.

After a brief drive we arrived at some worn down residential home. We walked inside and immediately noticed that the interior was far from residential. It looked more like a warehouse. There were folding tables set up everywhere and the entire space was filled with piles upon piles of brand new clothes.

Jeans, shirts, shorts, blouses, skirts, you name it. It was all there. We sat down with the owner and peppered him with questions.

“Where did this stuff come from?”

“What kind of business is this?”

“Who are these other people in the warehouse?”

All of his answers seemed very legitimate and before we knew it, we were developing our business plan. We would pay someone to build us an e-commerce website, we would do the marketing, sales and advertising, and he would do our fulfillment and drop shipping right from the warehouse.

And that’s exactly what we did.

Within a month we had a fully functioning website and a full time client services representative taking and processing credit card orders. Each morning I would set up our Google and Yahoo ad campaigns and then my mom, aka client representative, would handle all client email correspondences and orders throughout the day. Slowly but surely the orders came in. First New York, then California, and soon enough, we were taking orders from all over the world. Including Russia. But as the orders and sales grew, so did the complaints.

“What did you send me? I want my money back.”

“Theses clothes have been worn. Is this a joke?”

We thought it was a joke, so we took another trip down to see our wholesaler. “What is going on?” And so his responses began. “We just had some issues with our shipment company. It’s being resolved now, and we’ll be able to replace and take care of those bad orders.” He continued with more of the same and again, the answers all seemed legitimate. In hindsight, my BS detector should have been ringing a whole lot louder, but what did I know? I was just some bouncy ball businessman.

We went through a few more rounds of bad orders and even worse complaints until we got the very descriptive email that said people were going to come after us. And so with a hit on my back and a dysfunctional business, we shut down the operation and returned whatever funds we could to the very unhappy customers.

I learned two very important lessons that day.

  1. If it’s too good to be true, it probably is.
  2. Know who your business partners are.

The wholesaler was eventually arrested, and I eventually bought more bouncy balls.

South Beach Wine And Food Festival Beginnings

This post originally appeared on Forbes.com.

If you’ve ever done sales before you know how important customer service is. At the heart of any sale, there is mostly always good old fashion communication and relationship building. That is why I find it fascinating to look at how some of the best people in the hospitality business do what they do and how they think about all facets of an experience or of a relationship.

Take Lee Schrager as an example.

Fourteen years ago, Lee attended the food and wine classic to represent his company, Southern Wine and Spirits. After a wonderful experience, he decided to try to create an event that benefited his brands in a place that he felt would be more conducive to a larger and more influential group of people. He realized that to win people over he would need warm weather and a closer location to NYC.

Shortly thereafter the South Beach Wine & Food Festival was born.

Today, more than 60,000 people attend the events, and Lee is able to attract big names like John Legend, Chrissy Teigen and others.

I was able to chat with Lee to learn about three things that he felt contributed to the successful execution of this event. Here is what he said:

Leverage your unfair advantage. Lee was very quick to admit that part of his success with the event stems from the fact that he works for a large and successful organization, Southern Wine and Spirits. Having the resources of a large organization gives him a tremendous platform to get things in place however, this is just a part of the puzzle.

Engage with tastemaker and influential folks. In the first year of the event, Lee had no track record to speak of when it came to producing such large-scale events. So he reached out to his network and engaged with friends who become early adopters which in his case, were people like Emeril Lagasse, Rachel Ray, Bobby Flay and Giada DeLaurentiis, all highly respectful folks in the food industry. Couple this with the amplification of social media and the popular shows on the Food Network, and building an engaging audience was not too difficult for Lee.

Create great products, programing and listen to your customers. Lee and his team are very conscientious of different demographics, price points and customer feedback. As a result, they recently revamped the festival’s signature event – the Grand Tasting Village – to offer a brand new layout and timing based on festival goer feedback. They also added more late night events with cocktail themes, instead of only adding more of their traditional daytime events, and intimate dinners with chefs ranging from international superstars to local culinary talents.

Lastly, everything Lee does is done with a mission in mind and in this case, it’s charity. To date, Lee and his festival have raised over $20 million for the Chaplin School of Hospitality & Tourism Management at Florida International University.  The New York City Wine & Food Festival is hosted by and benefits the Food Bank For New York City and Share Our Strength’s No Kid Hungry campaign and 100% of the Festival’s net proceeds go toward helping these community based organizations fight hunger.

That’s not a bad mission to have, and with right skills and groundwork, it’s easy to see how an event like this can become and remain a success.

Nice job, Lee.

A Student – Learning, Living at the Intersection of Business + Technology + Innovation + Culture.