Get All Access for $5/mo

I Wanted to Visit San Francisco on Someone Else's Dime. I Ended Up With the Perfect Job. Here's what I learned from interviewing for a job I didn't really want -- but I got the gig, and it launched my career.

By Carol Roth

Opinions expressed by Entrepreneur contributors are their own.

Robert Alexander | Getty Images

While I have written quite a bit about my first job as an investment banking analyst, not many people know about the story behind how I got that job. Here's my story and some important lessons learned from the job that I didn't really want for the right reasons.

When I was in college, I took on quite a bit of debt. My father had taught me early on that debt was purely a financing tool, so I knew that I needed to get the best job that I could to pay down that debt quickly. That led me to a few options, including management consulting and investment banking. Because I wasn't someone who liked to go deep into one subject (I was a bit more "A.D.D."-prone), I chose investment banking.

Related: So, You Want to Be a What?

I submitted my resume on campus to the best investment banks around at the time, as well as some of the well-known and regarded boutique i-banks. One thing that I learned as I was going through this process is that if you made it past the first rounds of interviews, the companies would bring you out -- at their expense -- to their offices for a final round interview.

Then, my light bulb moment happened.

I had never been to San Francisco. My blue-collar family didn't really take many vacations, and I really wanted to see the city. So, I figured that if I could get an interview in San Francisco, I could check it out on somebody else's dime (before you "outrage" on the ethics of this, keep reading).

I submitted my resume to a boutique in San Francisco called Montgomery Securities, who selected me for an interview on campus. My plan was set into action until I had an issue come up.

I had a scheduling conflict on the same day that my investment banking interview was scheduled for. I was so determined to get that free trip that I had the nerve to call up the recruiter and explain that I had to miss my investment banking interview to -- and I am not making this up -- compete in a beauty pageant (Miss Illinois -- that's a story for another day, so just roll with me here).

As you might imagine, the recruiter was highly confused, as "investment banking" and "beauty pageant" aren't often uttered in the same sentence. I asked if there was an alternative way I could interview -- perhaps meeting a banker on the East Coast on another date. After much pleading (and perhaps some amusement over the thought of a pageant contestant turned investment banker), the recruiter ended up telling me that he'd consider and to call him back in a few days.

Related: 5 Ways Varied Job Experience Helps Your Career

I repeated the cycle of calling, pleading and being told to call back. After about 17 times, the recruiter said, "You are the most persistent *#@!*&$#% I have ever met. Fine, you can meet a banker in New York City."

After asking him if the firm could reimburse my train ticket to New York (I really had no shame), I locked in my interview.

The interview was a huge success and ultimately, I got my free trip to San Francisco.

Since the firm had been generous enough to do this, I took the interview process seriously, even though I really wasn't considering a West Coast relocation, especially when so much of investment banking was concentrated on the East Coast.

But something happened. While I didn't love the city that much (just being honest), I adored the firm and the people I met. They were young, aggressive and many were former athletes. It was a meritocracy, meaning, they cared more about performance than age, title or politics. And, at the end of my "free" trip, I realized that this presented an amazing opportunity for me to start my career.

I turned down some of the bigger-name investment banks and accepted my offer to work at Montgomery Securities in February of 1995 (with a July start date). It was the best decision that I could have made, giving me a ton of experience, working with fabulous and talented individuals and providing a platform for me to succeed.

I share this story, because it presents some time-tested learning opportunities.

1. If you really want something, be relentless.

While my motivation wasn't originally pure, I really wanted that trip to San Francisco. Being willing to follow up over and over again got me both what I wanted -- and also what I needed!

2. Always give your best.

You never know who might be watching your work or behavior and what that might lead to. I could have not taken the interview opportunity seriously, because I thought I wasn't interested. I would have seriously missed out on a tremendous platform had I not showed up with 100 percent -- even though it wasn't my intended goal.

3. Keep an open mind.

The path to what you want to have happen isn't always linear. As other opportunities present themselves along the way, don't ignore or dismiss them just because it's not the path that you expected. If you don't have an open mind, you just might miss out on something life-changing!

Related: Meet the Startup That Wants to Bring 'Sanity' to the Job Hunt

4. Do what is right for you.

While many of my classmates suggested that I pass on the offer from Montgomery and instead take an offer from a bulge-bracket firm or other more "prestigious" firm, I knew that I would thrive in a meritocracy. I did -- and I advanced much more rapidly than I likely would have at a "fancier" company.

Carol Roth

Entrepreneur, TV host and small business expert

Carol Roth is the creator of the Future File™ legacy planning system, a “recovering” investment banker, business advisor, entrepreneur and best-selling author. She is also a reality TV show judge, media contributor and host of Microsoft’s Office Small Business Academy. A small business expert, Roth has worked with companies of all sizes on everything from strategy to content creation and marketing to raising capital. She’s been a public company director and invests in mid-stage companies, as well.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business Solutions

The One Microsoft Design Tool Business Owners Shouldn't Miss

For a limited time, you can get a lifetime license for just $20.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Devices

Holiday Savings: Get a MacBook Air for $250

At this price, get one as a gift and one for yourself.

Franchise

5 Founders Who Transformed Franchising — And the Powerful Lessons Behind Their Success

Each of these franchise founders faced setbacks that could have ended their dreams. But they pushed through, creating brands that today feel like a part of our daily lives.

Starting a Business

Your Firsthand Experiences Shape the Way You Run Your Business — Here's How Mine Shaped Me

Growing up in a family-owned Chinese restaurant instilled in me the entrepreneurial spirit that now drives my tech venture. From handling customer complaints to managing staff, these early experiences shaped my approach to business and leadership.