Spencer Rascoff

Startups are hard. Hang in there, everybody.

Startups are hard. Hang in there, everybody.

As a kid, I watched a lot of entrepreneurship and that was inspiring to me and helped encourage me and my path to entrepreneurship.

As a kid, I watched a lot of entrepreneurship and that was inspiring to me and helped encourage me and my path to entrepreneurship.

Two of my companies, Hotwire, which had a crisis two years in, and then Zillow that had a crisis two years in with the financial crisis. My next company, Picasso, also had this crisis, which was the pandemic. Founders of startups who are listening to this, if you want a simple, safe, stable job, go do something else. That is not what startups are.

Two of my companies, Hotwire, which had a crisis two years in, and then Zillow that had a crisis two years in with the financial crisis. My next company, Picasso, also had this crisis, which was the pandemic. Founders of startups who are listening to this, if you want a simple, safe, stable job, go do something else. That is not what startups are.

Being provocative helps drive virality, and that's certainly one of the ways that Zillow grew.

Being provocative helps drive virality, and that's certainly one of the ways that Zillow grew.

I was always interested in entrepreneurship and business. I was the kid that would bake cookies and sell them on my street, that would get tracing paper and trace artwork because I wasn't a good artist, but I could trace things and sell those tracings to my parents' friends. So I was always hustling and trying to create businesses and make money. And I saw a lot of entrepreneurship all around me.

I was always interested in entrepreneurship and business. I was the kid that would bake cookies and sell them on my street, that would get tracing paper and trace artwork because I wasn't a good artist, but I could trace things and sell those tracings to my parents' friends. So I was always hustling and trying to create businesses and make money. And I saw a lot of entrepreneurship all around me.

My grandfather was a really successful entrepreneur in the apparel space. He had started a clothing company. My dad was a very successful entrepreneur. He started out as an accountant, and then he became, through a lot of hard work and also some good luck, ended up starting a business management company and tour production company that...

My grandfather was a really successful entrepreneur in the apparel space. He had started a clothing company. My dad was a very successful entrepreneur. He started out as an accountant, and then he became, through a lot of hard work and also some good luck, ended up starting a business management company and tour production company that...

had clients like the Rolling Stones and U2, David Bowie, Paul Simon, Pink Floyd, Leonard Skinner, and many, many others. And so I watched him pivot his career many times as the technologies of the music industry changed. So when platforms shifted from eight tracks to, I guess, records to eight tracks to tapes to CDs to streaming that had profound implications on how his business had to evolve.

had clients like the Rolling Stones and U2, David Bowie, Paul Simon, Pink Floyd, Leonard Skinner, and many, many others. And so I watched him pivot his career many times as the technologies of the music industry changed. So when platforms shifted from eight tracks to, I guess, records to eight tracks to tapes to CDs to streaming that had profound implications on how his business had to evolve.

As the concert industry changed, he moved more into touring and helped pioneer many aspects of the touring industry that we take for granted today, like the 360 tours where producers and promoters buy tours outright from the acts and flip the story on who works for whom and sell broad sponsorships for these international tours, et cetera.

As the concert industry changed, he moved more into touring and helped pioneer many aspects of the touring industry that we take for granted today, like the 360 tours where producers and promoters buy tours outright from the acts and flip the story on who works for whom and sell broad sponsorships for these international tours, et cetera.

So as a kid, I watched a lot of entrepreneurship and that was inspiring to me and helped encourage me and my path to entrepreneurship.

So as a kid, I watched a lot of entrepreneurship and that was inspiring to me and helped encourage me and my path to entrepreneurship.

I've always worked hard. I worked hard when I was a kid. One of my most formative experiences early on was playing chess. And I was basically, well, not quite a professional chess player, but I was a very competitive, serious chess player as a kid, I think, at college. Age 12, I was the fourth best chess player in the country.

I've always worked hard. I worked hard when I was a kid. One of my most formative experiences early on was playing chess. And I was basically, well, not quite a professional chess player, but I was a very competitive, serious chess player as a kid, I think, at college. Age 12, I was the fourth best chess player in the country.