If you take the origin stories of three of the most successful real estate entrepreneurs at the moment — the minds that brought us the real estate search portals Zillow and Trulia and the fast-growing brokerage and new franchisor Realty One Group — starting a successful real estate business starts with passion and ends with a lot of lessons learned.

In advance of Real Estate Connect San Francisco, which takes place Wednesday through Friday at the Hilton Union Square, Inman News reached out to three real estate entrepreneur heavyweights for their take on the entrepreneurial journey: Rich Barton, co-founder and executive chairman of Zillow Inc. (which, as of Tuesday afternoon, had a market cap of $2.08 billion); Pete Flint, co-founder and CEO of Trulia, (market cap $1.07 billion); and Kuba Jewgieniew, founder and CEO of 7-year-old Realty One Group, which according to Real Trends rankings is now the seventh-largest brokerage in the U.S. and one of the fastest-growing real estate firms in the country.

Rich Barton, co-founder and executive chairman at Zillow

Rich Barton

Rich Barton

What’s surprised you the most in the success you’ve seen as an entrepreneur?

It doesn’t seem like starting a business should be all that hard at the wide-eyed outset. Get a partner, raise some money, hire a team, ship a product …  it’ll all work out. Mike Tyson famously said, ‘Everyone has a plan till they get punched in the mouth.’ Growing a new business is the hardest thing I’ve ever done, and I wouldn’t have had it any other way.

If you had to do it all over again, which basic elements of the way you operated would you change or do differently?

Leading, recruiting, organizing and retaining people is the most important job of the entrepreneur. You’re a full-time evangelist, which means you’re always selling the big dream to someone.

Something I’ve learned over the years, however, is that some people just don’t fit for whatever reason, and trying to convince them otherwise or patiently waiting and hoping things will change for the better is wasted time and a drain on the organization. When it’s not right, don’t dilly-dally. Do what needs to be done so that everyone and the company can keep moving forward.

To be a successful entrepreneur …

You need to be an iconoclast, someone who can channel all the negative energy from the disbelief of others into a positive, disruptive force.

Pete Flint, co-founder and CEO at Trulia

Pete Flint

Pete Flint

What’s surprised you the most in the success you’ve seen as an entrepreneur?

The biggest surprise for me was the massive impact the right advisers and mentors can have for a company. At Trulia we have benefited from the insight of many different people, whether it was people from the venture capital firms that funded the company or the people who continue to serve on our industry advisory board to this day.

Getting the right advisers, people who will actually challenge your thinking and provide valuable feedback, can have a multiplier effect on the growth and success of your business.

If you had to do it all over again, which basic elements of the way you operated would you change or do differently?

One of the things we did right in the early days of the company was investing in the advisory board, attending conferences, and engaging with our counterparts throughout the industry.

Looking back, I think we could have invested more time and effort, perhaps hired more industry veterans, and put more people out in the field to make sure that our business and our intentions were clearly understood.

To be a successful entrepreneur …

Remember you don’t have all the answers and stay focused on your goal. Unforeseen challenges are inevitable, but if you can keep these two things in mind you’ll be better equipped to weather the inevitable storms that will come your way.


  • Dream big, but start small: You can’t do it all at once, and little victories along the way begin to accumulate.
  • Surround yourself with talent: This is easier said than done, but imperative to your success.
  • Innovation is a mindset: Specific good habits can create an environment that fosters innovation.
  • Culture starts from day one: Be deliberate about creating a great company culture and hire accordingly.
  •  Challenge yourself and your team every day: Self-discipline is a great way to accelerate improvement for yourself and your team.

Anything else you’d like to add?

Starting a company is one of the hardest things most people will ever do, so your business better be based on something that you are passionate about. There’s really no end to the demands of an entrepreneur. But what I’ve come to learn is that it’s a privilege to have the ability to choose the people that you will work with every day. That might be one of my favorite parts about my experience at Trulia.

Kuba Jewgieniew, founder and CEO of Realty One Group


Kuba Jewgieniew

I continue to be underwhelmed with how people accept being average and are unwilling to make the effort to improve — to be better! They don’t desire to advance (in business and/or life). I think part of it is that there is too much comfort in America, and it’s a challenge to shake up complacency.

If you had to do it all over again, which basic elements of the way you operated would you change or do differently?

We are learning that not everyone can keep up with the pace of our growth. Therefore we have improved our stringent qualification process to be certain there is alignment and that expectations are clear from day one on both sides. Most importantly, we focus on “believers” and those who fit our dynamic and diversified culture.

To be a successful entrepreneur …

Pursue your passion(s) relentlessly. Strive to be the best and don’t expect less than the best from anyone you associate with.

Pete Flint will be on the panel “The Industry Destiny: Imagine Your Industry in 2018” on Wednesday, July 10, at 3:45 p.m. Kuba Jewgieniew is not on the program but he’ll be at Connect. Have any entrepreneurial insights to share? Leave your comments below.

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