Second in Command Podcast – Episode 514
Andrew Eisbrouch – Scaling Secrets Fortune 500 Execs Don’t Want You to Know
Date: September 30, 2025
Host: Savannah Brewer (for Cameron Herold)
Guest: Andrew Eisbrouch, COO & General Counsel of Abrams Media
Episode Overview
This episode of "Second in Command" dives deep with Andrew Eisbrouch, whose journey spans from intern to COO and General Counsel at Abrams Media, culminating in the launch, scale, and exit of Law & Crime—a media company specializing in legal and true crime content. Andrew unpacks the lessons learned from building multi-platform brands, managing rapid growth, and transitioning from an operator to an owner. The conversation touches on bootstrapping, building resilient teams, navigating acquisitions, entering new industries, and fostering effective company culture as organizations scale.
Key Discussion Points & Insights
1. Abrams Media: The Portfolio & Evolution
[02:53 – 04:07]
- Overview: Founded by Dan Abrams (noted TV news legal correspondent). Abrams Media manages multiple digital brands:
- Mediaite.com: News and politics.
- Law & Crime: TV network, production, social media—true crime and live trial coverage.
- Bottle Raiders: Spirits (alcoholic and non-alcoholic) reviews, media, and events.
Quote:
“We have a news and politics site called mediaite.com ... a TV network and production company and social media business called [Law] Crime ... our newest project is a media company that focuses on the world of liquor and non alk ... constantly evolving those properties and launching more too.”
— Andrew Eisbrouch [03:10]
2. Career Path: From Intern to COO & Owner
[04:16 – 07:36]
- Connected with Dan Abrams for advice; took internship while in law school.
- Juggled drafting contracts and litigation as a law student.
- Balanced law classes with real-world business problem-solving.
Quote:
“Most of my ... more of my time [was] on that job rather than studying. ... professors would call on me and I’d just say pass ... the whole point of this is to get a job that I want to do well on.”
— Andrew Eisbrouch [05:43]
3. Value of Legal Background in Business
[09:20 – 11:00]
- Used legal training to speed up business processes—negotiating terms and contracting directly.
- Finds more fulfillment building and owning projects than serving as outside counsel.
Quote:
“I find being the client ... building something more fulfilling than ... working on the clock ... for another client.”
— Andrew Eisbrouch [10:45]
4. The Law & Crime Growth Story
[11:12 – 16:11]
- Joined as the first Law & Crime employee—literally started with names and competitive research.
- Pivoted from a legal website to live streaming murder trials—a market gap at the start of the OTT era.
- Bootstrapped the TV studio (initially worked out of a closet), then attracted strategic investment from A+E.
- Unplanned revenue growth came from selling production/content to major networks (Netflix, Max, A+E).
- Achieved viral growth during the Johnny Depp trial, becoming the #1 true crime channel on YouTube.
Quote 1:
“We were like, if we’re launching a TV network, we can plant our flag on all these platforms before it’s too late ... built out a very cheap version ... our studio was out of a closet.”
— Andrew Eisbrouch [13:11]
Quote 2:
“Our YouTube channel blew up during the Johnny Depp trial, because we were the number one place that was live streaming it ... the whole world was tuning into that trial.”
— Andrew Eisbrouch [14:38]
5. Exit & Life After Acquisition
[16:11 – 18:27]
- Sold to Jellysmack (global creator economy firm) for a reported nine-figure sum.
- Stayed on for a year post-acquisition, then shifted focus to Bottle Raiders (spirits/media/events).
6. Bootstrapping & Multi-Platform Strategy
[16:31 – 22:34]
- Always favored operating efficiently, bootstrapping before seeking outside capital.
- Believes in showing traction and proof of concept to improve leverage in negotiations/fundraising.
- Operated multiple business units (TV, web, production, social media) simultaneously so succeeding in one could fuel the others.
Quote:
“We were always of the profitability and bootstrapping mindset ... we’d be able to get ... a better evaluation if we showed them a product that had traction rather than just an idea ... so we launched ... very, very cheaply ... out of a closet.”
— Andrew Eisbrouch [16:33]
7. Adapting to Market Signals & New Industries (Bottle Raiders)
[19:50 – 22:34]
- Pursues businesses of personal interest and consumer passion (news, legal, spirits).
- Grounds new ventures in lessons from prior success: multi-platform approach, short-term revenue streams (e.g., events), hiring experts to offset personal knowledge gaps.
Quote:
“We really only pick businesses that we’re personally interested in ... But you have to see where the market’s going ... That’s what happened with Law & Crime and what we’re trying to do with Bottle Raiders.”
— Andrew Eisbrouch [22:57]
8. Transitioning from COO to Owner & Visionary
[27:34 – 31:16]
- Motivated by the "gambling side" of entrepreneurship.
- Sought a bigger stake in risk, equity, and vision after the acquisition.
- Bigger challenge: being the final decision-maker and articulating vision to motivate teams.
Quote:
“There’s a higher degree of pressure ... when you are the person that needs to make those final decisions ... you need to articulate the vision to people ... getting people excited about it ... that has to be even more of a focus than it was in the past.”
— Andrew Eisbrouch [29:41]
9. Communication, Managing Remote Teams & Clarity of Vision
[32:33 – 34:33]
- Noted contrast between in-person and remote team communication.
- Over-communicates priorities and initiatives in a remote setting—monthly all-hands, weekly team meetings.
- Uses Slack and standard remote tools for team cohesion.
Quote:
“If you’re in the office ... you know where we’re going ... when the team is all over ... they need to hear more ... you need to give them more context.”
— Andrew Eisbrouch [33:32]
10. Hiring for Culture & Skill You Don't Have
[35:49 – 39:20]
- Early-stage: prioritizes hunger, personality, and fit over direct experience—looks for a “record of achievement” and strong culture fit.
- Growth stage: hires more specialists/experts (e.g., CTO, industry experts).
- Relies on clear, measurable team goals and also observes team dynamics to avoid culture “toxicity.”
Quote:
“Personality is the number one ... I can tell if the person’s hungry, if they’re a hustler ... that has worked better for us than hiring someone more senior ... but the personality ... is not exactly what we’re looking for.”
— Andrew Eisbrouch [36:33]
11. Managing Performance and Accepting Imperfection
[39:20 – 41:13]
- Accepts that as you delegate, most hires won’t do things exactly your way but you must accept 85–90% to scale.
- Quotes about “80% done is better than 100% incomplete.”
12. Culture: Interest-Driven & Quick to Correct
[41:13 – 44:42]
- Ensures employees are actual fans/consumers of the product/vertical.
- If a hire feels wrong, prefers quick, decisive action (“gut is usually right”).
- Mistakes are OK—misfit in core values/personality aren’t.
Quote:
“You need to be like the audience/customer ... If you have a gut feeling that someone’s not going to work out, probably better to end it quicker than to drag it on.”
— Andrew Eisbrouch [41:17 and 42:11]
Notable Quotes & Memorable Moments
-
On bootstrapping and multi-platform strategy:
“We start like multi platform and multi like revenue from the beginning... one of them was going to take off, but we weren’t sure what... once one takes off, it fuels the others and reverses into it.” [19:50] -
On moving from operator to owner:
“It’s the gambling side of entrepreneurship ... put our chips back on the table ... take more ownership over, you know, over the business, both in terms of vision, financial risk, etc.” [27:34] -
On culture and hiring:
“If you have a gut feeling that someone’s not going to work out, probably better to end it quicker than to drag it on. Your gut is usually right.” [42:11]
Important Timestamps
- 00:00 — Finding audiences through multi-platform strategy
- 02:53 — Introduction to Abrams Media’s brands & markets
- 04:27 — Andrew’s non-traditional path: law student to intern to exec
- 11:12 — Launch and growth of Law & Crime; pivot to TV/network/production
- 13:11 — Bootstrapping with a “studio out of a closet”
- 14:38 — Viral growth during Johnny Depp trial (YouTube and social)
- 16:31 — Mindset around fundraising versus bootstrapping
- 19:50 — Multi-platform and revenue diversification as a media strategy
- 22:57 — Applying lessons from media to Bottle Raiders
- 27:34 — Motivation and process of moving from operator to owner
- 32:33 — Adapting leadership/vision sharing to remote teams
- 35:49 — Hiring priorities: culture fit, attitude, and managing what you don’t know
- 39:20 — Accepting 85–90% execution for scalability
- 41:13 — Ensuring team shared passion for the business
- 42:11 — Quick action on mis-hires—trusting your gut
- 45:00 — What’s next: launching the Drinks with Benefits non-alcoholic festival and partnering with ex-cable news figures for new media brands
Final Thoughts & Andrew’s Upcoming Focus
[45:00 – 46:11]
- Personally: Embracing fatherhood (newborn son)
- Professionally: Excited for Drinks with Benefits (NYC, September 27th), expanding Bottle Raiders’ events and media, launching/operating independent ventures for TV personalities (Alison Camerata, Jessica Yellen).
Connect With Andrew
- LinkedIn: Andrew Eisbrouch — Open for questions and expanding network! [46:37]
This episode is a masterclass in scaling, operator-to-owner transitions, and the realities of building media and consumer businesses from the ground up—with sharp, candid insights and pragmatic advice for COOs and founders alike.