Serial Entrepreneur Mike O’Brien: Keep Away From People Who Belittle Your Dreams

December 25, 2011

10:00 am

Mike O’Brien is one of those serial entrepreneurs that come up with new ideas – and execute them – constantly.  He is currently CEO of San Diego-based, a proactive career management tool that gives job seekers access to hundreds of thousands of recruiters.  He was a co-founder and served as CEO of, which now funds more than $45 million in student loans each month.  While there, he also created,, and

It’s always fun to delve into the background and motivations of someone who seems to never run out of viable ideas.  I was especially interested in how his latest venture was different from and LinkedIn – and he offered plenty of advice to other entrepreneurs who are just starting out.

Tech Cocktail (TC): Your career was built around education and financial aid.  Where did you come up with the idea for Climber – and why the switch to job searching?  Just a natural progression?

Mike O’Brien (MO):  My whole career has been a natural progression, actually,  My first business out of college was screen printing – my brother and I were partners – mostly for colleges and universities – and we did so well with online marketing that our clients started asking us if we could build them websites for their events.

So, we did, and we also started collecting domain names.  That led to – we just identifited the need and understood how to market it to consumers.  Then the leap to helping job seekers was almost inevitable.

TC: The online job search space is pretty crowded.  What sets Climber apart?

MO: There weren’t a lot of innovation in the job search space – most of the focus was on companies, not job seekers.  We wanted to give working professionals a place to say hey, this is what I want to do with my life.

Climber is not passive, and that is one of our major value propositions.  For example, LinkedIn SEO’s your name and background, but we SEO your skills to make it easy for recruiters – and anyone using Google – to find you for a specific job.

We also have a CRM system for job seekers – everything is tracked, so know which jobs you looked at, which jobs you applied to, you get reminders for interviews, etc. – and a recruiter directory.  The directory lets you click on a company name, and you’ll find the recruiters for that company so you can connect with them directly.  But, you don’t get the name of the recruiter – it is anonymized like Craigslist.

TC: Any interesting job or employment trends you’ve noticed as the economy sputters along?

MO: The numbers just came out – there is an 8.6% unemployment rate.  But what we’ve seen is that the people that log in to Climber and send an average of 5 resumes a day get a job twice as fast as those who don’t use the system regularly.  You get in, do the work, you get a job – it’s as simple as that.

TC: Tell me about some of your other ventures.

MO: My brother and I have a real estate holding company that focuses on commercial property, and I sit on the board of, which teaches doctors how to talk to patients.

I have found that I always want to do something I have no knowledge base in – I went from t-shirts into finance and then into careers.  I like to get into something new – you have fresh eyes and can bring new ideas to the space.

TC: What advice do you have for entrepreneurs just starting out?

MO: Start with an end in mind.  Understand your end goals and work backwards – otherwise your venture could end up feeling like it’s a job.  You can’t just decide this is what you want to do and you’re gonna be a millionaire.  Do the inverse.  I always said, hey, this is where I want to be, and these are the steps I need to take.  I need to do x to get the profit share I want, here are the margins I need, etc.

Be excited about the newness of it – overcome inertia and segment your friends.  It’s tough to be an entrepreneur – you will hear over and over again that your idea won’t be successful – so spend time with people who are supportive and share your passion.  Mark Twain cautioned, “Keep away from people who try to belittle your ambitions. Small people always do that, but the really great make you feel that you, too, can become great.”

TC: So, what’s next?

MO: Well, it doesn’t launch until April 1, but it is a company that basically marries the march madness concept with wine.  I love wine and want to learn more about it, so this is a way for me – and 10,000 other people – to do that in a really fun way.

[I got some additional information from Mike about this new company, and I will be covering it when it launches – so stay tuned!]

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Monika Jansen is a writer and editor who is happiest pounding out blog posts, newsletters, website content, and other materials. Follow her at: @monikacjansen