Episode 9: Restaurants, Archangels, & Digital Marketing in the Magic Quadrant with Elaine Cheng, InSITE DC (Georgetown JD 2018)

*You can skip ahead & Listen to the FULL interview RIGHT HERE!

Elaine Cheng

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Startups & Companies mentioned:

  • Sprout LA — “restaurant collaboration for unique dining in Los Angeles”
  • TrackMaven — “marketing analytics software”
  • Contactually — “web-based CRM to maximize network ROI”
  • Nordstrom — “shoes, clothing, jewelry, makeup, dresses”
  • Salesforce — “the customer success platform to grow your business”
  • Wilson Sonsini — law firm specializing in “technology, life sciences, & global enterprise”
  • FiscalNote — “legislative & regulatory analytics”
  • Startup Health — “entrepreneurs transforming healthcare”
  • SpaceX — “making life multi-planetary”
  • PlateIQ — “restaurant accounting made easy”
  • Partender — “bar software inventory in 15 minutes”
  • Active Protective— “hip protection for older adults”

InSITE Fellows, Alumni, & other folks mentioned:

Books, Resources, & Websites mentioned:


GUEST: Elaine Cheng, InSITE DC (Georgetown JD 2018)

[1:45] Meet Elaine, AKA Tiffanie on the West Coast #BestCoast

At 12 years old, I was already asking my dad if I could work as his office manager. When I worked for the Disneyland Resort, I was the youngest out of 600 hires (17 years old). In high school, I started a cupcake company and ran a subscription. In college, I convinced a culinary agent to hire me, and working at Sprout LA was one of the best experiences I’ve ever had.

[8:15] Intro. How did you first hear about InSITE?

Walking around the student fair in my first week on campus at Georgetown Law School, I saw a Venture Lawyers club right beside the InSITE banner. The guy at the table wasn’t even a JD, he was an MBA, Jordan Edelman. [We’ve had him on the podcast before! check out that interview here.]

But he was charismatic & totally sold me on the group in < 20 seconds.

[11:00] Impression. What was your 1st impression based on the application process?

I was hesitant to apply because the 1st year of law school is notoriously difficult. (Remember, we heard about this in Episode #3 with Beth Brandt!) So I submitted an hour before the deadline, had a great conversation with Pat Arunanondchai, and everything was smooth sailing from there...

Well, I mean I got accepted, but was still hesitant to commit, so the president Erin Rider (also a JD candidate) called me up and “strong-armed me into it”, said it was the best decision I would make.

[13:30] Jumping into work. Describe your FIRST semester consulting assignment.

TrackMaven is a SaaS platform that aggregates your online digital footprint and assesses performance versus competitors, tracking Big Data for companies like Nordstrom. On that project I got to work with Emily Teitelbaum, Adam Faircloth, and Michael Kelly. We came up with an internal marketing initiative to measure web impressions, bounce rates, market positioning, all that stuff.

Marketing is a soft spot for me.

[16:55] Pressing on. Describe your 2nd semester consulting project.

When I worked with Contactually, it was more outbound. They’re a new player compared to Salesforce, so we were trying to position them within Gartner’s magic quadrant: Leader, Challenger, Niche, or Visionary?

[19:15] Special Projects. What do you have planned for this semester?

By getting involved with a lot of the NYC InSITE Fellows this past year, I learned about the New York Angels. They’re led by ‘archangel’ David Rose, author of Gust and 3rd generation venture capitalist — now he’s my boss.

He talks fast, you can learn a lot in just a 4-hour meeting with these VCs.

[23:00] Events. What is your favorite event you’ve been to with InSITE?

On the Bay Area Trek [which we discussed in Episode #8 with Kelsea], I visited the law firm Wilson Sonsini which works with a lot of startups and actually took Google public.

Kelsea & Elaine side-by-side outside NerdWallet

I met a guy and started talking with him about working in WSGR’s SoMa office; he had worked as a VC before, and now was doing that type of work but within a law firm. So this summer I worked in their BizDev group.

Sometimes it takes 3:1 response ratio, 3 months of constantly checking in, to land your sweet summer internship… my parents call it stubbornness.

[28:00] Expect the unexpected. What was the most unexpected thing you learned about startup culture?

Have you seen the HBO show Silicon Valley? It’s not really like that at all.

I’ve been most surprised that it’s actually NEVER the same in any startup. As companies grow in DC, a lot of them relocate near Dupont Circle (just like one I visited recently called FiscalNote: open floor plan, glass-walled rooms named after clients, complete with beanbags and ping-pong tables).

[29:30] Investing. What was the most important thing you learned about investing this past year?

I was sitting at Verve cafe this morning in downtown L.A. and overheard a guy mention stocks. We struck up a conversation; turns out he was a hedge fund manager, plotting to make money off startups staying private longer:

“Speculation is off the charts… That’s what makes it exciting.”

[34:00] Angel Investing. Off the top of your head, what 3 companies would you angel-invest in right now?

  1. Startup Health — “entrepreneurs transforming healthcare”, by Unity Stoakes & Steven Krein (They run a video podcast I highly recommend.)
  2. SpaceX — “making life multi-planetary”. I love Elon Musk. A little bit of paranoia, a lot of genius. The Wall Street Journal reported that he tried applying to the Department of Defense for an open proposal, but only Boeing & Lockheed Martin were allowed to participate in the bid — he responded by suing the DOD on anti-trust allegations for open access, and then WON the contract from them on merit. “The squeaky wheel gets the grease… sometimes you just have to sue the company that you want to make your client.”
  3. PlateIQ — invoice accounting for restaurants and hospitality groups. Handling taxes is time-intensive and tedious, ripe for automation. When I was at Sprout, we worked with groups innovating front-of-house services (example: customer preferences for red vs white wine), but very few groups are building solutions like this for back-of-house. [Another startup example: Partender, “bar inventory in 15 min”, founded by my college mentor Nik Kundra — he was in 2016 Forbes 30 under 30, Food & Drink.]

[44:45] Advice. What is ONE piece of advice you’d like to give to current InSITE Fellows?

You really get what you make out of it.

I’m the new President of Georgetown Law Ventures (which is why I’m not on the executive board of InSITE this year) and we host VCs for discussions, as well as The Institute of Privacy & Technology and other initiatives.

[51:30] Shout-outs.

  • Jacob Wittman — the other InSITE DC Fellow who is a JD candidate.
  • As mentioned previously, Jordan Edelman & Erin Rider for recruiting me.


*starting at [52:30]

  • Whose face first comes to mind when you hear the word Entrepreneur? My dad, who started as a doctor and practiced for two years before pivoting into real estate.
  • What single daily HABIT is most key to your success? I wake up early enough to meditate ~20 min. and work out 10–45 min. every day because “Health is Wealth”. And keep reading, stay hungry.
Jim Rohn: “Either you run the day, or the day runs you.”

Patrick Lencioni: featured in Forbes Magazine, highlighting 3 characteristics that ultimately help employees succeed Hungry, Humble, Smart

Job advert for Evan Baehr’s startup, Able Lending
  • What book do you recommend to friends most often? The Startup Checklist by David S. Rose — get started on these 25 steps ASAP
  • What is the coolest startup technology you’ve seen recently? Active Protective’s airbag technology — “hip protection for older adults”
  • If you could swap lives with any person for a week, who would it be? Emma Watson. Hugely admire + respect her activism. (Check out her viral speech promoting the #HeForShe campaign at the United Nations.) Fun fact: she files her money into offshore accounts, as evidenced by the recent leak called Panama Papers.
  • What has been your biggest career failure in life? Going to law school instead of starting my own business.
  • Do you have an inspirational quote you like to remember in difficult times? I go through a quarter-life crisis SEVERAL TIMES A DAY.” → Recently my dad told me: “When the door isn’t open, jump through the window — I never give up… and the window might be closed, but it’s probably not locked.”

Outro: Rihanna’s B*tch Better Have My Money — “it brings out my inner twerk fiend”

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