ContextTV
HOW CAN WE BE HELPFUL?
YOUR VALUATION. OUR TERMS.
How Can We Be Helpful? | Episode 01
EPISODE 01 • 01 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 02 / 25
WatchMojo
Academic - fair use parallel
Confidentiality & engagement
Civic project and initiative
Purpose-driven
Rooted in Principles
Populism “give us the land” rhetoric was not gonna work (nor my style)
Really don’t want or seek anything.
Bottom line:
Yes, the People’s Wishes > Your Corporate Desire/Preference.
Free market.
Democracy.
Capitalism.
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 02 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
THE ULTIMATE QUESTION A FOUNDER ASKS
Why and when does an entrepreneur determine who do they invite to join their partnership? Last week’s Amnesia video…
And, what is their business worth—to conclude a transaction. Demand and supply…
EPISODE 01 • 02 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
2020 Transaction with Star Mountain Capital
Sold 25% of WatchMojo at a $90M Valuation.
$20M equity + debt (not really my preference… but debt gave investors certain Covenants, Rights, Vetoes).
Largely Secondary (vs Treasury).
Repaid full debt portion in 18 months. Very strong borrowing capacity & credit.
My original $250,000 equity investment achieved a 360× return on capital and a 52% IRR over 14 years. Even including all early capital (250K equity + $500K debt), the return was 120× with a 39% IRR — top-decile performance in private markets.
Never discussed it until…
EPISODE 01 • 02 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
FreeIran & The Peanut Project
EPISODE 01 • 02 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
Investor in Private Companies: Granicus Group “ABC”
EPISODE 01 • 02 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
Investor in Public Companies: Granicus Group “XYZ”
EPISODE 01 • 02 / 25
WatchMojo
Takeaway: I myself shift from capital appreciation to capital preservation…
Quebec Inc. parallel.
Meanwhile, index investing (all-time)
ContextTV
HOW CAN WE BE HELPFUL?
Granicus Group Long Term Vision
EPISODE 01 • 02 / 25
WatchMojo
ABC: Private investments | XYZ: Public Equity Portfolio |
Consulting, Analysis, Research: Peanut Project case study. | M&A Advisory (basically ran CIBC process, Oaklins less so) |
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 02 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 02 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
WHY TAKE OUTSIDE CAPITAL?
Early on? Seed. Growth. Survival.
In year 15?
Validation. Liquidity. Crystalize Capital Gains.�Governance. Succession planning.
Strategic help? (Are investors strategic or tactical?)
Every benefit has a corresponding obligation.
EPISODE 02 • 05 / 26
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
Why Star Mountain Capital?
EPISODE 01 • 02 / 25
WatchMojo
Founder Tony Chen
Ultimately, investors invest in People.
Products change.
Markets change.
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 03 / 25
WatchMojo
“Ash, these are crazy creative and really difficult to execute properly!”
“AI SLOP”
Cue violin music, but:
You want to partner with people who care about their reputation, as that shows that they will do the right thing (Principles) and not let Profit get in the way of your entrepreneurial Purpose or adversely affect your People and kill your Product.
Don’t Trust the Barbarians!
In any case, they’re open for business!
“We are Growing and Hiring! Please see the list of opportunities on our Careers Page.
Investing in the Growth Engine of America ® – Star Mountain provides: (i) Strategic Debt & Equity Capital to private businesses that have at least $15 million of revenue and under $50 million of EBITDA and (ii) Liquidity Solutions to investors and fund managers (“Secondaries”) including purchasing LP interests and direct investments in lower middle-market private credit and private equity funds in addition to providing fund managers with NAV loans.”
ContextTV
HOW CAN WE BE HELPFUL?
FROM CONCEPT TO REALITY
Capital is a means to an end.
The business plan is a roadmap, not a blueprint.
It’s not a question of “if” things go off the rails, but “when.”
EPISODE 01 • 03 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
THE CAPITAL LADDER
Savings → Debt → Angels → VC → Growth Capital → Private Equity
Every rung changes the bargain.
Mortgage vs Credit Card to buy your home.
EPISODE 01 • 04 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 04 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
THE CELL-MATE TEST
“Investors are your cellmate. Choose wisely.”
Capital is temporary.
Partnerships can outlive the honeymoon.
EPISODE 01 • 05 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
VICE’S CAUTIONARY TALE
Greed vs Fear.
Enterprise value ≠ equity value ≠ share price ≠ liquidation preferences.
And none guarantees a buyer. In fact, they scare them away.
EPISODE 01 • 06 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
BUZZFEED MEDIA DARLING
EPISODE 01 • 06 / 25
WatchMojo
Hundreds of millions in VC, PE & Strategic Funding
IPO’d via SPAC at $1.5B
Sold for a fraction.
Not controlling the outcome with MLB expansion…
Not controlling multiple contraction, AI, etc.
Not all that bad, but sure: “underwhelming.”
ContextTV
HOW CAN WE BE HELPFUL?
THE 3 VALUATIONS
Founder: long-term strategic potential. Expos? AceMojo?
Investor: risk-adjusted recovery.
Buyer: what can close today.
EPISODE 01 • 08 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
YOUR VALUATION. OUR TERMS.
Driven more by FEAR: Thank lawd I didn’t emulate Vice!
No liquidation preferences, No Puts, etc.
Seniority, liquidation preferences, redemption provisions and vetoes alter the waterfall.
A minority position can have major rights (eg. Vice Media).
EPISODE 01 • 09 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
A VALUATION IS A SNAPSHOT
Multiples compress.
Performance changes.
Buyers: A game of musical chairs.
The past does not guarantee the future.
EPISODE 01 • 10 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
P&L in the early, lean years
EPISODE 01 • 06 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
Jack of All Trades, Master of None - WatchMojo
EPISODE 01 • 06 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
Jack of All Trades, Master of None - OpenToWork.tv
EPISODE 01 • 06 / 25
WatchMojo
I used to worry we were late, but WatchMojo was early.
Similarly with MLB expansion, on Nov 29 2025, I thought it was a done deal, but again, very early.
WatchMojo experienced explosive, hockey stick growth curve from 2012 to 2016, then hit a wall, then found growth again.
Skipped VCs and went straight to Corp Dev (M&A)
Our valuation took off, and I largely handled M&A.
Main point: valuation can turn on a dime.
The main point is to stay in the game.
During summer 2026… people wondered “what happened to the Peanut Project?”
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 07 / 25
WatchMojo
ACE MOJO / EXPOS MEDIA
AceMojo allows us to skate to where the puck is headed.
It allows Expos to tap into Non-Basebal Revenues… but…
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 24 / 25
WatchMojo
Mr Dolan and Mr Dimon are illustrative profiles, not confirmed or implied investors.
Likewise, the immersive venue is a concept, and any savings from AceMojo-owned IP would depend on production costs, rights and programming economics.
ContextTV
HOW CAN WE BE HELPFUL?
EPISODE 01 • 24 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
NATURE OF PRIVATE EQUITY
Analyze a business with a history of revenues & earnings.
Develop an Investment thesis.
Establish Valuation (demand and supply)�Negotiate Terms.
Similar to how some investors prefer EXISTING teams and not EXPANSION teams (no revenue to value).
EPISODE 01 • 24 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
NATURE OF MEDIA
By launching The Lineup, are other sports media & sports business media more or less likely to cover The Peanut Project?
EPISODE 01 • 24 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
2022-2024: FROM TAILWINDS to HEADWINDS
Inorganic opportunities.
Core business.
Recognizing divergence in strategy and mismatch in philosophy…
Any regrets? Two.
EPISODE 01 • 10 / 25
WatchMojo
“TURBO”
(2021-2022)
ContextTV
HOW CAN WE BE HELPFUL?
A BIRD IN HAND
In 2024: Proposed a buyout. Gracious exit.
Fear vs Greed.
No transaction.
EPISODE 01 • 11 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
THE TIME-HORIZON COLLISION
The fund needs realization.
The company needs reinvestment.
The founder needs continuity.
Who bears the mismatch?
EPISODE 01 • 17 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
THE PROCESS… PROCESS
Interest is not intent.
An IOI is not an LOI.
An LOI is not committed financing.
A signed deal is not a closed deal.
EPISODE 01 • 14 / 25
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
WHAT DOES “HELPFUL” MEAN?
Advice? Introductions? Patient capital?
An orderly exit? Simply getting out of the way?
Define it before signing.
EPISODE 02 • 18 / 26
WatchMojo
ContextTV
HOW CAN WE BE HELPFUL?
THE FOUNDER’S PRIORITIES
Protect the Team.
Protect the Treasury.
Protect your Reputation.
Protect your Company.
EPISODE 01 • 20 / 25
WatchMojo
AKA
It’s ok to be selfish
(if you are unselfish/selfless.
If you were self-serving, I’d advise the opposite).
ContextTV
HOW CAN WE BE HELPFUL?
NEXT: Ep 2. MISSIONARIES & MERCENARIES
EPISODE 01 • 25 / 25
Control of your own destiny.
The story remains to be written.
Just watch.
WatchMojo