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13 Reasons Why Bootcamp is Worth it

Interested in Bootcamp, but not sure if you should do it? Here are 13 reasons why the CEO Bootcamp is worth it.

Jerry was inspired to co-create the CEO Bootcamp to address recurrent problems and challenges he saw faced by his clients- some of the most recognizable startup CEOs and founding teams. (Jason Calacanis & Jerry sat down to talk about the most common themes in one of the most popular TWiST episodes: 6 Biggest Mistakes Founders Make.) Since 2013, the Bootcamps have had a big impact in the lives & companies of the CEOs who have had the courage and curiosity to join us.

If you’re like many CEOs who have contemplated coming to a CEO Bootcamp, you might be wrestling with a few questions and trying to justify the cost.

I asked Bart Lorang, CEO of FullContact, what he would say to any CEO on the fence about coming to bootcamp because of the following questions you might be asking yourself:

Q. Is it the right time?

BL: The sooner the better.  If you screw up your job as CEO, you might not have a company.  So best to get started early.

Q. Are we too early/young of a company?

BL: If you’re early, it will have an even more dramatic impact. If the bootcamp can improve your overall value of your business 10% per year, I’d rather have that 10% earlier so that the value compounds.  I wish I would have attended a CEO bootcamp in 2011.

Q. How do I justify the cost?

BL: As Brad Feld said – “it’s worth an infinite amount” – but I look at it more pragmatically: if your company is valued at $2M, will the $10K investment in yourself improve the performance of the business and increase the value of the company by more than $10K or 0.5%? The answer is YES – the actual number is likely much, much higher. It’s a no-brainer.

Q. How do I convince my co-founder/board/investors/employees/spouse?

BL: CEOs need the proper training as well. The fact that you have to ask your board/co-founder/investors/etc. permission demonstrates to me EXACTLY why you need to attend the CEO bootcamp. You are the CEO, right?

If you need more reasons, and some good reading, I’ve included more great articles below so you can rest assured that the topics covered at Bootcamp impact your company’s bottom line.

And your heart might thank you, too.

The topics covered at the CEO Bootcamp impact your company’s bottom line. See for yourself:

Overcoming Impostor Syndrome

“[People who suffer from impostor syndrome] are not the only ones who pay a price,” she continues. “The cost to their companies in terms of unrealized human potential can be enormous. … When qualified workers fear risks, get caught in the ‘expert trap’ and are prone to perfectionism and procrastination, there’s a leak in the corporation’s human resources pool.” – Via Forbes

Cofounder Relationships That Work

“A common reason for startup fatalities, particularly in the early days, is some sort of conflict between co-founders. One of the main reasons for co-founder conflict is that many aspects of the relationships were either ill-defined or misunderstood. To minimize the chance of this, it’s critical that you and your co-founders come to agreement on some key issues.” – Via David Cohen

YOUR happiness is incredibly valuable to your company.

“Happier people are more successful, more creative, energetic, resilient,” says Crabtree. “They work better together. They absorb more information. They have more tools in their tool belt to help them handle whatever life throws them. They are healthier, they live longer — and they show up at work more often.” via FirstRoundReview

Your Mom loves you, but everyone else is going to quit if you act like an asshole.

“Authors Marcus Buckingham and Curt Coffman said in their book, First Break All the Rules: What The Worlds’ Greatest Managers Do Differently, that people don’t leave jobs, they leave managers. If employees don’t get along with their managers, don’t like them or don’t respect them, they will leave a company despite a high salary or great benefits. A bad manager is a big factor in employee performance. A good manager, no matter the salary, will inspire loyalty.” via Forbes

A CEOs self-awareness can make or break a company.

“Without self-awareness, you cannot understand your strengths and weakness, your “super powers” versus your “kryptonite.” It is self-awareness that allows the best business-builders to walk the tightrope of leadership: projecting conviction while simultaneously remaining humble enough to be open to new ideas and opposing opinions. The conviction (and yes, often ego) that founders and CEOs need for their vision makes them less than optimally wired for embracing vulnerabilities or leading with humility. All this makes self-awareness that much more essential.” via Harvard Business Review

Effective leadership doesn’t just happen naturally, it takes intention and practice.

“[Many new leaders] know how things should be done, and subsequently provide too much direction and not enough positive feedback, thereby affecting people’s status. They often don’t provide clear expectations, impacting certainty. They micro manage, impacting autonomy. They want to maintain a professional distance, impacting relatedness. And, they may impact fairness by not being transparent enough. When the opposite happens and you meet someone who makes you feel better about yourself, provides clear expectations, lets you make decisions, trusts you and is fair, you will probably work harder for them as you feel intrinsically rewarded by the relationship itself. Spending time around a leader like this activates an approach response and opens up people’s thinking, allowing others to see information they wouldn’t see in an avoid state.” via NeuroLeadershipJournal

 Your time is your most precious resource.

“Knowing when it is the right time to start handing things off and hiring is an art not a science. It has something to do with the availability of resources. And it has something to do with the scale of the organization. When the CEO is still scheduling her own meetings when there are over fifty employees, something is wrong.” via

Quality. Not quantity.

“In fact every hour you put in over 40 hours a week is making you less productive, both in the short and long term. Studies have found that the “sweet spot” for optimum productivity is 40 hours a week.” via Lifehacker

Being CEO is hard. Really hard. But you’re not the only one who struggles. And there is support.

“Be open about your feelings–don’t mask your emotions, even at the office, suggests Brad Feld. When you are willing to be emotionally honest, he says, you can connect more deeply with the people around you. “When you deny yourself and you deny what you’re about, people can see through that,” says Feld. “Willingness to be vulnerable is very powerful for a leader.”” via Inc.


Embracing Leadership as a Reluctant CEO This essay is written by one of our first alums from our CEO Bootcamp, Sooinn Lee, CEO of LocoMotive Labs. Last fall, Sooinn also spoke at TEDxBayArea Women in a…



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