The first time Greg Waldorf pitched business to a potential client, he was only 13. Starting with an Atari 400 computer, he had learned to program and started working with businesses in the Los Angeles area. When clients selected him to write software, his parents had to sign the contracts.
That was 35 years ago. Waldorf has led multiple tech startups since then. His current mission is to help people who are not unlike his teenage self: entrepreneurs, self-starters, and those working in the burgeoning freelance movement. His company, Invoice2go, enables “gig economy” workers and small businesses to bill their clients on the spot and get paid using their mobile phones. In his words: “Look more professional, save time, get paid faster.”
Invoice2go was founded in Australia in 2002 by a small-business owner who was annoyed by the complexity of existing accounting software. Waldorf took over as CEO in 2014 with the goal of turning the company into a global software powerhouse — on mobile devices. Today the company serves more than 200,000 customers worldwide. Waldorf, who earned his MBA from Stanford Graduate School of Business in 1994, was formerly the CEO of eHarmony, the online dating website, and he has been a board member and advisor at companies large and small, including 11 years at Trulia and Zillow. He also serves on the boards of Grovo, VTS, VivaReal, and ProPublica.
Who are your primary customers?
The biggest bucket is home services: anyone doing something around the home, like electrical, construction, plumbing. The next category is freelancers, such as writers or designers. The third type are highly mobile workers: mobile DJ, dog walker, makeup artist.
What do you think is the future of work?
We are in an unstoppable trend in which more people are working in more flexible work environments. That includes independent, part-time workers in the gig economy. Technology can help them operate in a way that used to be associated only with larger businesses or people with tech skills. Software can make up for that gap.
What is the biggest misconception about this group of workers?
A lot of people think that part-time, gig-economy workers are unable to get full-time work. But 94% of Invoice2go customers say they have no interest in stopping their side gig to go back to full-time work.
Why is that?
The ability to control your own destiny is the biggest thing.
Are there other forces for this change, beyond just wanting to exercise their free will?
Technology. I took a Lyft ride last week from a guy who takes that route home from his full-time job, so if he takes a fare, it pays for his commute. It used to be harder to think about how you could make money for two hours on your own schedule. They are looking to use their time more wisely in a more satisfying and more lucrative way. The notion of working for a single employer for the bulk of your adult life is not an expectation most people have anymore.
How do you think the U.S. election will impact your business?
A majority of our customers are not in the U.S. Globally, our customers want a reduction in regulation and bureaucracy. My hope is that governments at all levels — federal and local — continue to do things to help small businesses focus on growing, hiring, and succeeding. We think it’s hard here, but it’s even harder elsewhere. In the U.S., we don’t think much about opening a business bank account, but in other countries it can be complicated and expensive. Then there are the fees and the time it takes to register a new entity. Most of our customers are focused on improving cash flow and being more efficient with their time, so the biggest thing you can do for them is get out of the way.
How does Invoice2go help with that?
We lower the barrier to getting started. When you start a new business, the first thing you need to do is find a customer; the second thing is to get paid. Our customers can be up and running in five minutes, sending invoices and accepting card payments. Small businesses sometimes forget to invoice for work they’ve done. With our mobile app, they can invoice as soon as the work is complete, on the spot. We also make it possible to accept a credit card payment with no fixed monthly fees and no need for a bank or a terminal.
Is mobile your main competitive lever against the QuickBooks of the world?
It’s speed and simplicity. We give you the benefit of mobile and cloud software without having to set up financial accounting systems. Most small businesses don’t think about or understand or want to set up a balance sheet. They want to keep it simple.
Do you remember when your love of business or technology began?
I started working in tech when I was 13. It was the early 1980s. I was fortunate to be able to get an Atari 400 computer. It had 8K of RAM. It gave me a path at a really young age to do something unusual. I presented to CEOs at executive off-sites. When you’re a teenager, that is awesome. The typical teenage experience is an angst-filled fishbowl of peer pressure, but this gave me access to people who were older and who gave me affirmation that I was doing something well.
Who “discovered” you and helped you see what was possible?
My first big client was an investment real estate firm in Southern California. The CFO hired me to write software to power the front end of their business. Looking back on it, the guy took a huge chance on me. When you’re a kid, you don’t have a sentimental sense about things — you just want to get it done and break it down. That’s why so much innovation comes from young people.
Everything great in my professional life, I would attribute to being involved with tech. I’ve learned about how technology can powerfully affect people and business for the better. With eHarmony, I had the opportunity to help people find love. Invoice2go makes a big difference in customers’ lives by helping them have more control of their schedule and get paid faster and look more professional.
You are a serial entrepreneur. What still surprises you?
People-related issues come to you in endlessly new sets of circumstances. I’ve built what I think of as my own personal best practices: Be straightforward, be transparent, don’t be overly clever in the way you try to deliver feedback, and make sure people know you care. But new people issues always come to you.
What is the same?
I just assume that business is going to be hard. That doesn’t mean it won’t be fun, but I wake up every single day thinking things will be challenging.
How do you keep that from paralyzing you?
What we are doing is important. We are supporting hundreds of thousands of small businesses. I have a responsibility to my colleagues and investors to make this a success. I find a huge amount of satisfaction in helping other people to be successful in their roles.
Is selling to consumers different or the same as selling to small businesses?
They are both pretty hard to reach because there are a lot of them. But when you’re successful, they tell a lot of friends. It’s not about having a big salesforce; you have to reach customers digitally.
What is the best business book you have read?
One I’m fond of right now is called Monetizing Innovation. It explains that you have to develop your products from the ground up to be something your customers want to pay for.