Big Ideas
- Prior to launching Shutterstock, Jon had worked on ten different companies and Shutterstock was the byproduct of these ten companies. Being flexible and open to making hard pivots is a muscle that Jon says entrepreneurs need to continuously strengthen.
“I know for a fact, if there’s an idea I have, it’s going to pivot into something else so give that that’s a fact it comes down to the people that are going to operate the ideas and people that are going to drive those businesses forward”
- When Shutterstock was launched, Jon had the classic entrepreneur ‘chicken and egg’ problem. Before photographers would be interested in using Shutterstock he needed to find users, and users would not be interested until there were photos on the website. Taking matters into his own hands, Jon went out and took the first 30,000 photos for the website himself.
“Back then we were ahead of our game I think because I personally and the people in the room with me personally felt the pain of each step so that we could reduce that friction for the actual customers”
- Jon now resides in Miami, which he believes is the up and coming tech city. He works with new entrepreneurs and helps to build Miami companies with his investing company, Pareto Holdings.
“Being in a new place and having lots of new ideas and meeting new entrepreneurs and trying to match them with ideas, fund them and get them to a successful place, it’s been really fun and I want to continue to do that”
0:13 Jon’s Morning & Night Routines
For his morning habits, Jon starts his day with coffee and tries to get in some road cycling as often as he can. At night, Jon tries to get 8-10 hours of sleep.
“I know a lot of people that try to sacrifice sleep to get more stuff done, I think that’s a bad strategy. I’ve always been a big fan of those 8 hours”
1:25 Context Switching
He’s gotten used to context switching since he started his first companies in college. From being involved in many companies throughout the years Jon has recognized the patterns between them.
“I think it’s really important to build that muscle, it can be painful but it can be built”
3:37 Investing Framework
When it comes to investing he looks primarily at the person behind the company.
“Often the idea doesn’t matter as much because most of the time the first idea the entrepreneur come up with is going to be different than the one that is actually a success”
When it comes to early entrepreneurs, Jon says they need to have flexibility, which he learned from his companies prior to launching Shutterstock.
“Shutterstock was the byproduct of ten different completely different businesses”
6:07 Early Entrepreneurship
When asked what kept him excited as an entrepreneur, Jon says it was the fact that he knew he was getting better and better each time.
He explains the ten companies prior to Shutterstock all had a software background but they all were ultimately failures.
“If you look at entrepreneurs and study where they started from and how they got to where they are, often it’s a very twisty, windy, crazy path”
7:50 Hard Pivots
While working with other entrepreneurs, Jon says that some are much better at accepting the hard pivots than others.
“The people that kind of learn from it, and then take what they learned, test a new idea, and go back out into the world and do it again, each time they get stronger and stronger and you can see it”
8:48 Idea Generation & Sourcing Entrepreneurs
From creating ten separate companies prior to Shutterstock, it’s clear Jon has a knack for idea generation. He says this process has changed throughout the years but it’s currently a spreadsheet with a list of ideas and people that can execute on those ideas.
This list of people is a variety of people Jon has worked with on Shutterstock, other entrepreneurs he has guided, and even just people on LinkedIn that he comes across and feels as though their background would fit the company idea he has.
When it comes to people he has worked with on his own companies, Jon says some are interested and some are not, it all comes down to their entrepreneurial sensibility and the pace of working they prefer.
“I remember thinking back to people that would get frustrated being in a larger company and those are the people that have that entrepreneurial mindset. Those are the people that I reach back out to that I’ve worked with in my past that are interested in these types of environments”
12:26 Sink or Swim
Jon says that the only way to be an entrepreneur is to know it’s either sink or swim.
“I can provide advice, I can provide guidance, I can provide experience, but they are the Chief Executive Officer of that idea.”
If the entrepreneurs that Jon works with makes a decision that he disagrees with, he lets them because he knows it’s their role as the leader of that idea.
“There could be something that I don’t realize myself, they are deep in that idea, they are going through emotions of being in the weeds on that idea”
14:20 Rising Tech in Miami
Jon has always been a contrarian when it comes to creating companies in the tech industry. From building tech businesses in New York City when all tech success was in Silicon Valley and now residing in Miami, Jon has a knack for knowing the up and coming tech hotspots.
“This is a process, it takes time, it’s not going to happen overnight like I said and it didn’t happen overnight in New York, but I think Miami will be a great place in the future where there will be plenty of tech companies here”
16:47 Long Term Thinking
Jon says he learned the hard way that things are not going to happen quickly.
“If you want to build something super big it’s not going to happen in one year, it’s not going to happen in two years, and those first few years are going to be painful and it’s going to feel like you’re not making a lot of progress”
In the beginning of his career, Jon says he was thinking in shorter time frames.
“There’s two time frames you are working on. You’re trying to get every single thing that possibly can get done that hour, that day, that week, that month, in like really short quick sprints, but you have to think of the long term and what you’re building at the end of the day”
19:56 Changing the Business Template
Jon says that when he was in New York sourcing people to join his team for Shutterstock, it was before New York had the ‘crazy instant check ecosystem’ that it has today. Instead of focusing on raising capital, Jon says in the beginning stages of Shutterstock they were just focusing on product-market fit and the ins and outs of the business model.
Jon names Miami, Austin, and Chicago as business friendly cities that are open to new ideas of how businesses are done.
“I hope instead of just adapting to the template, we have other places we can form something new here”
23:06 Working In All Roles
Jon says that instead of hiring the people he thought he needed during the early stages of Shutterstock, he did the jobs himself.
“I think that’s a really important lost skill in entrepreneurship, is jumping into something you’re not good at and just doing it”
During the first month of Shutterstock, Jon worked the roles of customer service, the photographer, the programmer, the voice of the customer, and those
“When you can raise money so fast and just hire a customer service person that worked at a competitor of your own business, they’re going to do it like they did it at your competitor, they’re not going to do it the way you think you can do it better because you actually felt the pain and did it yourself”
25:00 Becoming His Own Client
Jon explains how when starting Shutterstock he had the chicken and egg problem that any business has, he didn’t have content creators or customers.
“What I did was I was the first content creator. I went out and I shot 30,000 stock photos and tried to put myself in the shoes of what it means to be a stock photographer.”
Jon says that by going through the motions himself, they built the most efficient upload engine of any of the photography sites out there for commercially model released photography.
“Back then we were ahead of our game I think because I personally and the people in the room with me personally felt the pain of each step so that we could reduce that friction for the actual customers”
29:52 Network Effects
Subscriptions, marketplaces, and going through the effects of each step in the customer interaction process are some of the main ways Jon says he created a network effect.
Jon references the never ending reciprocal system of block chain, Bitcoin, and Twitter.
“These are super important pieces of the future that are network effects”
While the world has gone back and forth on block chain ideas, Jon believes the decentralized system conversation is coming back.
34:35 Jon’s Current Projects
Jon spends half his time on Shutterstock as Executive Chairman and the other half on incubating businesses.
“When you think about how the world is changed with Covid, the way people work, the way people live, I’m focused on a lot of those big changes”
Among these big changes, Telemedicine is one of the projects Jon is working on.
“People have gotten much more used to the remote aspect of everything and so these are kind of these big changes that I’m looking at for the future of businesses”
36:57 Seeking Help
Jon says there isn’t a specific group of people that he would consider mentors but that he has people throughout his career that were very helpful for him.
“I’ve always been someone that asks a lot of questions and that’s how I’ll continue to operate”
37:50 Risk
When it comes to risk, Jon used the strategy of ‘multiple irons in the fire’.
“I know for a fact, if there’s an idea I have, it’s going to pivot into something else so give that that’s a fact it comes down to the people that are going to operate the ideas and people that are going to drive those businesses forward”
Jon says it comes down to fewer entrepreneurs than ideas and so the entrepreneurs need to constantly iterate and be able to pivot.
“It’s about distributing the risk with a single entrepreneur that can handle multiple ideas”
39:00 Entropy of People Management
When it comes to the different stages of his businesses, Jon says it changes at every stage.
- Less than 10 people → “Okay, I can manage this”
- 25 people → “You know everybody’s names still, you can kind of manage that”
- 100 people → “There’s probably someone coming in and someone leaving every month”
- 250 people → “You don’t know everybody’s name, and someone is coming in and someone is leaving every week”
Jon says he got to about a thousand people, but looking back thinks he should’ve stopped at six or seven hundred people.
“You need to feel it out because no one knows when that timeline ends and they’re like my skill set has run its course”
42:16 Guiding New Entrepreneurs
Now Jon focuses on evaluating the entrepreneurs that he works with and providing guidance for them. John asks them, “what do you think you’re good at and what do you think you’re not good at.” He says that this question is often the hardest thing for entrepreneurs to come to terms with.
“The trick of being an entrepreneur is to really start to understand kind of where your own personal limits are”
When working as the CEO, Jon says you have to consider who you will hire to fill the roles that you are not good at.
“The trick is to make sure you haven’t gone too far and actually caused the company to go backwards before you hire for things you need to hire for”
45:00 The Importance of Self-Curiosity
When it comes to what the entrepreneurs ask Jon, he says they probably don’t question what they’re good at and what they’re not good at enough.
“They don’t often ask me or themselves what they’re good at and what they’re not good at, I’m finding at least. That’s a question that as an entrepreneur you have to constantly be curious about”
46:05 Get In The Weeds
Jon says he is always trying to get people to ‘go into the weeds’ on specific pieces. For example, since startups are limited by cash, Jon recommends that instead of hiring for roles, take on each role even if you don’t have the experience in that piece of the business model.
“If you just hand it off, you can have some blind spots that could be success or failure for your business”
48:00 Entrepreneurial Regrets
Jon says it’s not worth looking back and thinking of moments that him and his team spent too much time on one thing.
“This is the hardest part of being an entrepreneur is kind of challenging yourself and what you’re good at and what you’re not good at. Being okay with doing the things you’re not good at for a limited amount of time to learn exactly what you need to learn about those things and then finding the right time to hand those things off”
49:15 Taking Shutterstock Public
Shutterstock was growing and had predictable revenue and Jon says going public was the right decision in 2012 and continues to be.
“You build a lot of that quarterly discipline that is really important for a company to be the best it can be and you also get to use the public company structure to be efficient”
Despite the positive effects of taking a company public, Jon says that being public is hard.
“At the end of the day I think it makes you a stronger more resilient company and my experience with Shutterstock showed that”
51:31 Memorable Days at Shutterstock
At Shutterstock, Jon says going public and ringing the bell and watching the first shares trade was among some of the most memorable and joyful days. Some others he lists are when they got to 10 million of annual revenue, then 100 million dollars of annual revenue, and paying out 1 billion dollars to their contributors.
“These were goals that seemed really hard in the beginning but are amazing when you get to them”
52:52 Daily Drive
Jon says that the second he tries to relax he gets the ‘entrepreneurial itch’ back.
“I don’t think it’s going away so I stopped resisting at this point”
Jon says that coming down to Miami is an exciting opportunity as a new territory for him and new tech companies.
“Being in a new place and having lots of new ideas and meeting new entrepreneurs and trying to match them with ideas, fund them and get them to a successful place, it’s been really fun and I want to continue to do that”
53:50 Unrelenting Grind
Although Jon says he was working 24/7 in the early days of Shutterstock, he doesn’t think it is necessary to be as imbalanced as he was in order to be successful when starting a company.
“It all comes down to personality at the end of the day, but in the beginning it was a constant grind to make sure I really optimized every minute of every day to make the company the best it could be and get ahead of my competition”
54:43 Calling All Entrepreneurs
Jon says that if you want to be an entrepreneur in a certain area or you have a great idea for a new company, you can reach out to him or Pareto Holdings website and social accounts.
“I’m constantly looking for ideas and entrepreneurs and willing to fund”
56:06 Jon’s Dream Interview
“When it comes to his passion for that product and what that company has turned into, that would be an amazing person to talk to”
Connect with Jon