You don’t have to have all the answers — focus on asking great questions.

 

Marc Gorlin is the CEO and founder of Roadie, the first “on the way” delivery service that puts unused capacity in passenger vehicles to work by connecting senders with drivers already going that way. Marc has been a successful serial entrepreneur for more than 20 years and actively speaks on technology, innovation, and venture funding.

Where did the idea for Roadie come from?

The idea for Roadie struck me one day when my remodeling project stalled out. I ordered tile from a manufacturer, but it was smashed to bits when it reached my doorstep. There was a warehouse a few hours away that had a couple boxes of tile, but I had no practical way of getting the tile that day except for making the five-hour round-trip drive myself. I knew there had to be someone already making that trip who would be more than willing to throw my tile in his or her trunk for $20. From that problem, Roadie was born.

What does your typical day look like, and how do you make it productive?

If I wanted a typical day, I’d be an accountant. Every day looks different for me, but that’s a huge part of what makes building a company so exciting.

How do you bring ideas to life?

When you start something — no matter how small — you need to accomplish something real every day. Sometimes that means picking one thing and constantly building upon it. Consistent movement and progress separate startup success stories from well-intentioned failures in those early, fragile times.

In business and in life, decisions will get you stuck in the mud faster than anything else. There are a million things you need to figure out when you start a business, and there is simply never enough time to put the required amount of thought into every single choice. You often do more damage waiting than making a wrong decision and fixing problems down the road. Perfect is the enemy of done, so make an educated decision and move on.

What’s one trend that really excites you?

From retailers to airlines, everyone is thinking about delivery. That obviously makes us really excited. At Roadie, we see a future beyond inefficient, inflexible, and asset-intensive logistics models. Instead, our communities can better use existing resources to enable unprecedented efficiency, flexibility, and sustainability to address the pressing transportation challenges of our modern age.

What is one habit of yours that makes you more productive as an entrepreneur?

We have this monumental goal to change the world of logistics, but this overarching aim comes down to day-to-day tactics, meetings, and emails. When you’ve got that much to do, it’s easy to be busy and hard to be effective. I would be lost without my to-do list; it keeps me focused on what needs to get done that day or that week, and it helps me ensure nothing falls through the cracks.

What advice would you give your younger self?

Predictions or answers are less important than asking the right questions. Those questions — and the courage to raise your hand and ask those questions — will ignite your imagination and ultimately become the center of your career.

Any of us can make predictions about the future or try for the right answers. But more than anything, stay curious to see how it all shakes out. Follow your natural curiosity. Ask great questions. Raise your hand. Don’t waste time trying to look smarter than you are. You don’t have to have all the answers — focus on asking great questions.

Tell us something that’s true that almost nobody agrees with you on?

I make a point of meeting every potential Roadie hire in his or her final interview, no matter which team or role. It drives my team crazy and takes up my time, but it’s worth it. Culture builds community, and it’s the people who make Roadie such an incredible place to work — they’re driven and passionate, and they truly care for one another and what we’re building. One bad hire can torpedo the entire spirit of a team, and that’s not a risk I’m willing to take.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Entrepreneurs never have enough time and always have too much work to do. It’s sometimes hard to even pull your head up to see whether the work you’re doing is as important as you think it is.

I always have 19 plates spinning, but I try to slow things down from time to time and do something I wouldn’t normally have the time to do. When we first announced Roadie, I was inundated with more than 500 emails a day. I heard a customer service rep talking to a potential Roadie who was very uncomfortable giving us his driver’s license and insurance information. He had a lot of questions and asked whether he could speak with me directly because I was the guy he had been seeing on TV. I heard the rep say that I probably wouldn’t be able to talk to him about the issue.

When he hung up, I asked the rep for the man’s number and called him directly. I made him feel comfortable that there were people he could get a hold of because he’s doing us the service of trying us out. Could I have talked to everyone who called? No way. Impossible. But I could do it for one.

I try to continually remind my team — and show them through my actions — that no matter how busy you get or how many plates you’re spinning, you can always do for one.

What is one strategy that has helped you grow your business?

When you’re getting the job, don’t think you’re just getting the job — you’re getting the keys to the whole damn building. It’s not enough to connect with your boss or your immediate team. You need to make connections with people on the other side of the office.

Talk to people in the break room. Find out who’s in charge of various departments and introduce yourself. Offer to help. Buy someone a cup of coffee. Always look for new and better sources that can expose you to different aspects of the business. Every minute you spend investing in people instead of checking your email will pay dividends for the rest of your career.

Back in the early days of Kabbage, the guy who funded our Series A investment round was someone who I had never met before. I only met him because I knew someone who knew someone who knew someone who then introduced us to him. Fast-forward a few years later, and he also led the Series A round for Roadie. You can’t plan for that.

Chances are that the most exciting and meaningful connections you’ll make in life won’t come from your immediate circle. Whether it’s a spouse or a business partner, sparks happen when you go a few degrees outside your comfort zone. We got funded because I followed up with someone four people removed who eventually introduced me to the right guy. I got into the mix, and I got lucky. One thing I know for certain? The harder I work to meet people, the luckier I seem to get.

What is one failure you had as an entrepreneur, and how did you overcome it?

I previously co-founded a company named Kabbage, which helps small businesses gain access to much-needed capital online. When we started raising money for Kabbage, the first round of financing was $1.5 million and took us more than 18 months to complete.

While funding for any new business is hard, we faced a unique challenge because the market for financial services was in shambles. We had nothing but an idea and relied on statistics and industry trends when pitching. Most days, we pitched to blank stares across the table. People weren’t connecting with our idea, which led to slow funding.

We discovered that we were not telling a good story that resonated with anyone on a personal level. A friend introduced me to a storyteller working in the startup space. She told us to stop pitching and start telling a story, so we threw out our boring PowerPoint deck crammed with text and stats that nobody could process.

We started leading with a story about Bill, a small business owner who couldn’t get a fair shake from Rich, a stereotypical big banker who only saw Bill as a credit score. We told it with cartoons, and we told it with heart. Once the audience cared about Bill, we were able to show how many other “Bills” were out in the world.

Creating a story that resonated literally made the difference in more than $250 million in funding and more than $4 billion we were able to lend to small business owners. It’s an investment in time and money that most entrepreneurs don’t see value in, but it’s been invaluable to me. No matter what you’re pitching, lead with something personal and human. Make people care, and be a storyteller.

What is the best $100 you recently spent?

Buying eight large pizzas for a group of Atlanta Roadie drivers. We frequently ask drivers to come into the Roadie office to share their experiences with the app, meet our team, and give suggestions for new product features. Meeting our community of drivers, hearing their stories, and listening to how they think Roadie can be better is worth the $100 investment every time.

What is one piece of software or a web service that helps you be productive?

Highfive. You might not have thought that videoconferencing would make my list of best productivity apps, but it helps me stay connected to my team when I’m on the go. I still send a lot of emails, but face-to-face communication moves the needle faster.

What is the one book that you recommend our community should read?

“The Hard Thing About Hard Things” by Ben Horowitz. It gives real-world solutions and advice to problems businesses face every day.

What is your favorite quote?

“The woodpeckers inside the boat can do more damage than the storm outside.” All the competitors, outside business forces, and economic downturns combined can’t do the damage of a few toxic team members.

That’s why culture and team are my single biggest focus. A candidate might be great at marketing or sales, but he or she won’t make the cut at Roadie if he or she is too self-absorbed to empty the dishwasher.

Key Learnings:

  • Do for one. No matter how busy you get, you can always take the time to help one person out.
  • Perfect is the enemy of done. Make decisions and move on. You’ll learn not to get sucked into the vortex of making things harder or bigger than they need to be.
  • Read “The Hard Thing About Hard Things” by Ben Horowitz. It gives real-world solutions and advice to problems businesses face every day.
  • Your team is everything. Invest the time necessary to build a great culture and community.
  • Be a storyteller. Lead with something personal and human, and find a way to make people care.

Connect:

https://www.roadie.com/

Marc Gorlin on LinkedIn: https://www.linkedin.com/in/marcgorlin

Roadie on LinkedIn: https://www.linkedin.com/company/roadie-inc

Roadie on Twitter: https://twitter.com/Roadie

Roadie on Facebook: https://www.facebook.com/roadie/