Most people were probably just stepping into entry-level jobs that they didn’t love, trying to figure out their career and how to navigate the landscape of their new roles and industries.

Right now Josh Kayser is 30 years old, and the CEO of, an online startup that is now in its 7th year of growth and record-breaking revenue from the surety insurance space, a billion dollar space you’ve probably never heard of.

Like myself, Josh was only 23 when he started his company. is comprised of a team of mostly millennials, and his executive team is all 30 or younger, and they are still crushing their competition in the surety insurance space. When Josh was 23 he pitched strategic partnerships to boardrooms full of executives twice his age, negotiated the terms he wanted, and began to build his empire in the surety space.

Yes, there are many young entrepreneurs that decide to go against the grain and take the less traveled road of employer vs. employee, but Josh and his story are still unique.

Josh was thoughtful and methodical about choosing the kind of business he wanted to start.  Unlike many young college grads who launched companies for bragging rights or get-rich-quick dreams, Josh identified an opportunity to modernized an industry that hadn’t yet been modernized by new technology or processes.

Instead of trying to reinvent the wheel, Josh just sought to make that wheel much better.

After learning more about Josh’s founder journey, I wanted to know more about how he actually did all of these things at such a young age during a down economy.

There are the 3 character traits that Josh says best served him throughout his 7 years building this business from nothing, which especially gave him an advantage over his competition:

Tip #1: Be Bullish

Startup founders have to be hard headed and able to handle hearing ‘no’ over and over, but also not comfortable accepting it as the answer. If you’re the type of person who is shaken by rejection or criticism, you shouldn’t start a business, especially a disruptive one that defies the status quo.

Change is scary for most, and there will always be critics and naysayers. You have to bear down, power through, and buck when you’re getting pushed against a wall. You have to teach yourself to see beyond the pushback and reluctance and instead, focus on your mission to be an agent of change and forward movement.

If you can anticipate that this is just part of the process, you’ll be able to handle it much better.

Tip #2: Question Authority

We are taught all throughout childhood to respect and subscribe to authority.

Our parents, teachers, professors, bosses and those our senior know what’s best, right?

At some point, you reach a point where you’re no longer a child, and you learn you have to question what you’ve been taught or you’ll go through life being a sheep who just blindly follows what others say.

While demonstrating respect to authority can be good for business, you shouldn’t be afraid of questioning it either.

If you think you can do something better and can show results, jump on that opportunity immediately. Don’t be afraid to learn new things, and roll up your sleeves and get dirty to figure out how things work, or how you can make them better or more efficient.

With that attitude, you can become an expert and master at whatever you’re doing.

Tip #3: Avoid Self-doubt

Founders don’t have enough time to waste it on questioning themselves with self-doubt.

If every business owner mulled around on important strategic decisions until they felt 100% confident before executing, every business would die.

You need to make decisions efficiently if you want your company to be successful. While it’s great when you have facts and research to back up your decisions, you shouldn’t be afraid to quickly pull the trigger and get things done.

You might not always make the right decision the first time, but you can also fix things later.

Don’t be afraid to fail, and if you do, fail fast and forward.


The opinions expressed here by columnists are their own, not those of


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