Q&A: Director / Management at Tech Startup and Media Unicorn

Hi everyone

I've benefitted a ton from WSO over the years and would love to give back -- thought this would be a great starting point.  Have had a very untraditional career path but traversed through very traditional types of roles. My current role is as untraditional as it gets and that gives me access to all different types of people, problems, strategies, and roles.  Throughout it all I made it my main goal to differentiate myself, which is one of the most important skills in my opinion.

-Current Director at a tech start-up and media unicorn (current focus is on relatively large capital raises, growth through M&A, strategy, and operations)

-Works directly with C-suite across all facets of both businesses (worked way up from intern in <2 years)

-Co-founded and operated SPAC for 1 year, target focus in the media and technology space

-Started and leads a real estate development company with operations across the eastern seaboard

-Founded and leads a private investment company that extends small bridge loans, venture debt, and invests in public and private equity

-Spent two summers as SA at Morgan Stanley (ER and M&A)

-Economics and Political Science B.A. from Non-Target Liberal Arts School

Ask away!!


Want to work with me? Check my profile here

WSO Elite Modeling Package

  • 6 courses to mastery: Excel, Financial Statement, LBO, M&A, Valuation and DCF
  • Elite instructors from top BB investment banks and private equity megafunds
  • Includes Company DB + Video Library Access (1 year)

Comments (7)

May 11, 2022 - 9:50am
BobTheBaker, what's your opinion? Comment below:

Hello, I'm also a director at a startup. I'm sure I'll have many questions. Can you provide more detail on your career progression? How did you navigate securing equity? What is your current comp? Where do you see your career going next? What's your day to day typically like?


Most Helpful
May 11, 2022 - 12:19pm
techfin5, what's your opinion? Comment below:

Great -- ask away.

Career progression was SA at BB --> sales support at startup --> finance dept for cap raise at startup --> SPAC management --> back to multiple startups in more broad role.  Have leaped quickly thus far and have done so by being thorough, quick, and deliberate with my work.  More importantly, impressing people that you work with on a day to day and being enjoyable to work with.

Securing equity is all sales.  Sell yourself.  I believe that everyone at a startup should have equity and you should not be hesitant to ask.  Can provide more detail here on how the conversation should flow given your current equity situation (have 0 versus minimal).

Comp is comparable to IB assoc but more is salary versus bonus.

At some companies I work for, I was fortunate enough to get in at early points.  Would love to stay around and grow with these companies.  But, could also be interested in the startup life and being a staple for certain needs that startups have.

Day to day is usually at desk around 7am to settle in, catch up on emails from night before, plan out the day, and use 7-8 as time to check in with people i work closest with.  8-10 is usually meetings (team meetings and touch bases with folks that I have P1 projects in process with). Usually lock in from 10-1 to do my own work, reading, strategy organization etc.  Afternoons are when we have team syncs, larger meetings.  A lot of the stuff I do is project management and serving as proxy for CEO on everything.  Also use the strategy side of my brain to plan the business into the future and develop shot term goals that enable us to reach those heights.

May 11, 2022 - 4:17pm
2rigged2fail, what's your opinion? Comment below:

Would be great to hear about the SPAC, investment and real estate businesses you founded. What size are/were they and how did you attract capital with relatively little experience? What assets do you look at and own? thanks

  • 1
May 12, 2022 - 8:50am
techfin5, what's your opinion? Comment below:

Thanks for the Q.  Will first start with the capital part of your question -- I had a pretty good base of capital underneath me.  Most of this was savings from past jobs that had been conservatively invested in the market or accumulated in 'don't touch' accounts.  Even to today, I usually get a paycheck in and wire out to numerous don't touch accounts -- you have pay yourself first.  The best thing in the world is letting these accounts accumulate then being able to deploy.

After doing this for a few years, I had a nice chunk of money.  Looked at my situation (was in college) and said what is unique here -- realize something that I had that most didn't was time.  Post-college its all about making money in reasonable amounts of time, but I had 4 years of school and boozing --> might as well use that time productively by laying tracks for the investments to mature over time.

The first thing I bought was a piece of swamp land in Florida where it took me almost 2 years to get permitting, etc in order to build a house on the property.  Houses in certain parts of Florida are like buying cars: go to the show room, pick out what you want, pay the builder to build that for you (called spec homes).  Did that and turned a pretty nice profit in it so kept reinvesting in the business.  This business continued to grow through that reinvestment and that enabled me to grow into other types of business ventures in the real estate space.  Now, we tend to look for houses or parcels in zones that would warrants 6-12 unit apartment buildings with minimal variances and approvals -- this enables us to move quickly.

When covid hit, two things happened -- there was excessive printing of money and business were trying to give themselves enough of a cash cushion to make it through -- these two realities created opportunity.  The printing of money had the biggest effect --> it brought down rates so money was cheaper for my RE business and, in a completely untraditional thought process, it would most likely diminish the long term returns in accessible investments (oversimplified and not completely defendable --> more people investing, less to go around).  Because of this, if money was to be made, needed access and ability to invest in less accessible ventures that are not tied to underlying accessible investments.  By accessible, I mean 'who can invest in these' --> can joe blogs down the way get his money in here, if yes, its accessible.  This led me to start my investment co.  Started by extending small bridge loans and then it grew into convertible financings and that just took us into an entirely different mindset where we no longer were focused on niche parts of the market but more focused on unaccessible investments.

These businesses along with my day job and small, tight alumni base at my school gave me access to people and opportunities.  This is how I entered the SPAC world --> through connections.  My day job focus area, finance knowledge, maturity, and tenacity to outwork anyone and everyone opened this door.  It was an amazing experience, made some amazing connections which have helped propel me forwards.  

All of this is great stuff, but I would be shallow minded not to mention luck.  Half of it is luck.  But I believe that luck follows the worker.

Thanks for the Q -- welcoming all follow ups.

Learn More

300+ video lessons across 6 modeling courses taught by elite practitioners at the top investment banks and private equity funds -- Excel Modeling -- Financial Statement Modeling -- M&A Modeling -- LBO Modeling -- DCF and Valuation Modeling -- ALL INCLUDED + 2 Huge Bonuses.

Learn more
May 12, 2022 - 9:43am
techfin5, what's your opinion? Comment below:

Quo tempora aut qui ab in neque et. Ipsa neque eos saepe at quae facere sapiente. Aut at laudantium ipsa ut. Sit delectus quo veritatis iure repellat quisquam. Aperiam consequatur delectus voluptatum veniam.

Voluptatem reprehenderit aut sed ullam architecto. Molestiae dolorum laborum tenetur libero. Aliquam veniam quam beatae voluptatem.

Start Discussion

Career Advancement Opportunities

June 2022 Investment Banking

  • Jefferies & Company (▲03) 99.6%
  • Lincoln International (= =) 99.2%
  • RBC Capital Markets (▲07) 98.8%
  • Houlihan Lokey (▲07) 98.4%
  • Bank of America Merrill Lynch (▲01) 98.0%

Overall Employee Satisfaction

June 2022 Investment Banking

  • Lincoln International (▲06) 99.6%
  • Jefferies & Company (▲11) 99.2%
  • Greenhill (▲07) 98.8%
  • Rothschild (= =) 98.3%
  • Evercore (= =) 97.9%

Professional Growth Opportunities

June 2022 Investment Banking

  • Jefferies & Company (▲04) 99.6%
  • Lincoln International (▲04) 99.2%
  • RBC Capital Markets (▲09) 98.8%
  • Houlihan Lokey (▲07) 98.4%
  • William Blair (▽01) 98.0%

Total Avg Compensation

June 2022 Investment Banking

  • Director/MD (9) $661
  • Vice President (37) $394
  • Associates (188) $246
  • 2nd Year Analyst (115) $162
  • 3rd+ Year Analyst (17) $156
  • 1st Year Analyst (363) $149
  • Intern/Summer Associate (75) $147
  • Intern/Summer Analyst (286) $91