Isaac Oates is the Founder and CEO of Justworks, a cloud-based platform that helps entrepreneurs and businesses grow with confidence by giving them access to big-company benefits, automated payroll, HR tools, and compliance support — all in one easy-to-use technology platform. Isaac comes from a unique tech background, having worked at Amazon, Etsy, and Yahoo! while serving as an intelligence officer in the National Guard and Army Reserve for 12 years. Isaac founded his first startup Adtuitive back in 2008, which Etsy later acquired, and experienced the frustration of endless paperwork, exorbitant costs, and hours spent on the administrative side of running a business, which led him to the idea behind Justworks in 2012.
Entrepreneurial Role Models:
When business started difficulties overcame:
“where it got really really hard was about nine months in, we had built a product, albeit a basic one, and we had a couple of customers but not very many, and we were running out of money. And getting more money at that point was extraordinarily difficult because my track record before Just Works didn’t really matter anymore, and my track record at Just Works wasn’t looking that good because we hadn’t proven a lot of the important things I think investors wanted to see. So that was unbelievably challenging. We almost ran out of money, we were probably about six weeks from running out and it was really scary, personally was really challenging to get up every morning and to stay motivated. Although like I mentioned before I was unwilling to fail and so I got up every morning anyway, and amazingly so did my team. And we got up every day and we all did everything we could think of to kind of move things forward. Eventually I found an investor who was willing to invest in then things just kind of started rolling from there and really it has been like an amazing story ever since. But those first kind of 18 months were incredibly challenging”…[Listen for More]
Favourite Books:
Understanding Michael Porter: The Essential Guide to Competition and Strategy Book by Joan MagrettaFavourite Quote:
“Plans Are Worthless, But Planning Is Everything” President Dwight D. Eisenhower
Recommended Online Resources:
AVC – Fred Wilson is a VC. He writes something every day. This is his diary, his sandbox, his therapist, and more than anything it is his bar where he gets to be the bartender. AVC is a place where everyone is welcome and the conversation is civil and lively.
Best Advice to Other Entrepreneurs:
“believe in yourself. Keep taking steps one at a time and believe in yourself”…[Listen for More]
More About Isaac Oates:
Neil’s Quote at the Beginning:
“A successful man is one who can lay a firm foundation with the bricks others have thrown at him.” David Brinkley
Other Quotes From the Chat with Isaac Oates:
- “I wrote down beforehand why the business should exist”
- “it really is a journey and I have learnt so much over the past six years about myself, about leadership, about business and I think it is that curve and just climbing up it ”
- “I think self-awareness and self-mastery are probably the two key ingredients in success in I think success in all parts of life”
- “I think great leaders, they know themselves, and they know where they want to go and how to take people with them”
- “I think about things on kind of a life-cycle. Everything you can think of has a birth and eventually a death and everything falls apart eventually”
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