by Brian DeChesare Comments (9)

How to Break into the Finance Industry by Creating Your Own Brokerage Job

Brokerage to Finance

What should you do if you graduate with a not-so-great GPA in a relatively small market?

Most people would say, “Give up” or “Apply to a Master’s in Finance or MBA program and turn yourself around there.”

But there is another option: Create your own job.

And then leverage that experience to break into the finance industry.

Our interviewee today did just that and used his experience as an independent broker in Canada to win offers in infrastructure private equity and real estate.

I was intrigued when I heard his story, and he was nice enough to share everything:

Breaking into Finance through the Side Door

Q: Can you summarize your story?

A: Sure. My parents were immigrants who made most of their money in real estate, so I had always been interested in investing.

I attended a top university in Canada and studied accounting at first.

But I didn’t like it, and I found my audit internship at a Big 4 firm boring, so I quickly switched to finance and started trading stocks.

I did a few finance internships and eventually worked at a royalty financing provider – a firm that provides capital in exchange for a percentage of revenue rather than interest – and gained experience working on debt deals there.

Many of the deals were small ($200K to $5 million), and many interns at the firm cold called companies all day to source transactions.

I sourced several deals there and realized I could do it independently and earn more if I received commissions from each deal rather than a fixed hourly rate.

So, I operated as an “independent broker” for around a year, closed several smaller deals, and then leveraged that experience to win offers in infrastructure private equity and real estate development.

Q: That story sounds too good to be true.

First off, don’t you need a wide network to run a brokerage business? How did you develop that as a student/intern?

A: I met many lenders in my time at the royalty finance company; there are many “crown corporation” lenders here that fund companies that are too small for institutional investors.

The main challenge was finding clients, i.e. companies that wanted to borrow money.

I cold called to win most of the deals, and I found contact information using three strategies:

  1. I searched for companies with some refinancing risk (e.g., those with a debt maturity in a few months and insufficient cash to pay for it).
  2. I contacted companies that pitched themselves on shows like Shark Tank and Dragons’ Den – they didn’t necessarily want to use traditional debt, but they were sometimes open to royalty financing that charged a percentage of revenue.
  3. I reached out to boutique investment banks, introduced myself, and offered to pass along bigger deals (anything above $10 million) to them. In exchange, they referred smaller deals to me.

Q: But why did any of these borrower companies take you seriously?

You were young and barely had any industry experience.

A: When I cold called firms, I initially said, “I’m calling on behalf of [Royalty Financing Company Name], an established lender, and I wanted to discuss your company’s financing needs.”

My previous company was fine with that as long as I referred larger deals back to them.

I found out later that borrowers didn’t want to hear that because it sounded like I worked exclusively with my former company.

So, I modified it and started saying, “I’ve worked with lenders such as [A, B, and C] to provide financing to companies such as [X, Y, and Z].”

If you’re polished on the phone, you won’t necessarily reveal your age; they knew I wasn’t 60, but most people assumed I was in my early-to-mid 30s.

If they asked about my marital status or if I had kids, I always had answers ready.

I met the key people in-person only at the end of each deal – and no one wanted to lose a transaction at that point because I looked “too young.”

Q: But even if you made yourself appear older, why did these companies pick you over an established boutique bank or another broker?

A: I charged no consulting fee, no retainer, and no upfront fees. I just collected a standard percentage on the back-end if we closed the deal.

Also, I didn’t demand exclusivity, so the companies were free to reach out to other brokers as well. Whoever closed the deal first would earn the commissions.

I could offer those terms because I didn’t “need” to earn a certain amount: I did the job mostly to gain a network and leverage the experience for future roles.

Q: It seems like that structure would create a lot of risk for you, though.

Didn’t you have to do a huge amount of work for each deal?

A: Yes, it was difficult to juggle this effort with school and other internships for almost a year.

The deals I worked on took anywhere from several months to nearly a year to close. And these were very small deals – hundreds of thousands to the low millions.

I did a lot of legwork, but I saved myself time in a few ways:

  • I was careful with client selection and quickly de-prioritized any company that seemed “iffy” or not worth the time/effort. The fact that I didn’t charge upfront fees or request exclusivity gave me the flexibility to do this.
  • I never created a pro-forma model, CIM, or other documents until lenders requested that information from the client. Many lenders in this lower-middle-market space had very specific requests, so there was no point to creating generic documents.

Q: OK. But then you stopped this effort after about a year and moved on.

A: Yes. I had always intended to leverage the experience to win a job offer elsewhere (private equity, real estate, or subordinated/mezzanine lending).

I did earn commissions from a few closed deals, but the income was unpredictable, and the effective hourly rate wasn’t great.

Also, I wanted to buy a property at around this time, and it was very difficult to get a loan as a “self-employed” person.

Leveraging Your Own Brokerage Business

Q: And how well did your plan work? Was this experience useful?

A: The brokerage experience helped me win future real estate and lending roles and even an infrastructure private equity role.

But I’m not sure if the skill set was the main benefit – the network might have been more helpful.

For example, I once won a job because the firm was a common counter-party with a lender I had worked with, and the lender recommended me.

Q: Would you recommend this strategy for other fields? Or does it only work for roles that involve debt in some way?

A: I don’t think it’s super-helpful if your goal is a private equity mega-fund or pension fund.

But the skill set and network could be valuable in real estate, lending, and smaller PE funds where you have to source deals.

I also received a lot of interest from investment banks after I began listing this experience on my resume, but I really did not want to do banking.

Running this type of brokerage business is similar to working at a search fund: You get good experience, but it’s either unpaid or in the “you won’t make money for a long time” category.

But the advantage is that you can learn more about the entire capital structure; at a search fund, by contrast, you learn less about financing and more about operations.

Q: OK. Would this strategy be useful to students who are at good schools but who lack solid grades or work experience?

A: Potentially, yes. If you’re in that position, I would say: “Don’t focus 100% on the bulge-bracket investment banking to private equity path.”

Yes, everyone is obsessed with PE, but even with best academic credentials and work experience, you have a very low chance of getting into the mega-funds.

And if you don’t have top credentials, well, good luck.

But if you’re willing to go through the side door, there are tons of interesting opportunities in lending, real estate, and infrastructure.

Q: Great. Any last tips or advice?

A: Learn to love the grind.

Many students say they’re “networking,” but in my experience, few take it seriously and do it consistently.

Throughout undergrad, I did 3-5 coffee meetings per week and connected with alumni like that.

Finance here is a small community, but that can also make networking more effective: Everyone will refer opportunities to you since they’ll know you’re looking.

Q: Thanks for your time.

A: My pleasure.

M&I - Brian

About the Author

Brian DeChesare is the Founder of Mergers & Inquisitions and Breaking Into Wall Street. In his spare time, he enjoys memorizing obscure Excel functions, editing resumes, obsessing over TV shows, traveling like a drug dealer, and defeating Sauron.

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  1. Avatar
    Zec Cepeida-Conner

    Hi Brian,

    Working to start my own brokerage presently and was hoping you could put me in contact with your interviewee, or at least give me their name so I can try and contact them. Hoping for some insight and potentially some guidance as I work to get my business off the ground.

    1. This interview is from a few years ago – I can reach out to the interviewee, but I haven’t been in touch in a long time, so no guarantee he will respond. If you reply to one of the newsletters here with an email reminder, I’ll be more likely to follow-up with him.

  2. I followed a similar if less calculated plan to land an acquisitions director position at a small real estate private equity fund. Networking and specifically learning to confidently reach out and make new connections is key. Learning to manage both sides of a deal through to completion was also valuable experience. By the time I was interviewing I spoke the language fluently and could do the numbers in my head so the lack of a big name school wasn’t an objection.

    1. Nice, glad to hear it!

  3. I have a career question. Would it be weird to do two part time internships? Currenlty a colelge student

    1. It’s fine, it’s pretty common actually.

  4. Good article.

    I just moved to the US and the create your own job opportunity is an angle I’m considering, but for Real Estate; specifically Multifamily properties. But rather than parley this for IB/PE etc. roles, I want to do my own deals and stand on that for B-School.


    Please and thank you.

    1. I think it’s viable, but the issue will be getting a work visa/permit to do that. I’m not certain how the laws work when you are self-employed rather than working at a mid-to-large company. But yes, real estate to IB or other finance roles or business school is viable.

      1. Thanks!

        I have the requisite permit.

        Your articles continue to inspire and educate.

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