Issue No. 40Week ending Sunday, October 4, 2026485 episodes · 2075 articles
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Private equity

Ryan Milligan on Private equity

9 quotes from 1 episode on Private Equity Funcast, each with a timestamped link to the source.

9 quotes1 episode

The short version

Ryan Milligan states that private equity compensation structures often contain hidden risks for operators. Securing LLC profits interests prevents executives from writing personal checks to exercise traditional stock options.

Most interesting insights

Refusal to share distribution waterfall models during hiring indicates a sponsor intentionally conceals potential downside economics from incoming managers.

“I just think it's about somebody hesitating to share information. If somebody I've heard people have been told, 'We don't share the waterfall.' But that's I don't know. I'd say, 'Well, then let me talk to your boss in that situation.'”

Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 37:22 ↗

From Spotting Red Flags in PE Equity Grids and Rollovers

Sponsors introduce tension near a sale by waiting until the last minute to demand executives roll 30% of proceeds into a new buyout.

“On the sale where this also gets tense is private equity firm is selling and they they wait too long toward the end to say, 'Oh, by the way, another private equity firm is buying and they need you to roll 30%,'”

Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 40:17 ↗

From Spotting Red Flags in PE Equity Grids and Rollovers

Operators typically receive flat equity percentage quotes that only apply to the residual common equity pool.

“So what's probably going to happen is you're going to get quoted a percentage…”

Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 7:12 ↗

From Why a 1% Equity Pool Slice Yields Far Less Than Expected

Top talking points

  1. LLC profits interests provide upside without upfront cash

    Getting profits interests through an LLC structure is the most tax-advantaged path for a manager. This setup grants equity upside in a sale without demanding out-of-pocket capital.

    “So wherever possible we use what are called profits interests…”

    Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 8:11 ↗

    From Why Profits Interests Beat Stock Options in PE Equity Pools

    “Those are the most tax advantaged situations for a manager. Getting profits interest as part of an LLC structure is probably what you want.”

    Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 8:27 ↗

    From Why Profits Interests Beat Stock Options in PE Equity Pools

  2. Traditional stock options force executives to write personal checks

    To start the clock on long-term capital gains treatment, stock options carry a strike price. Operators actually write personal checks to take possession of the shares.

    “The issue with stock options is it actually requires you so there'll be a strike price and you you'll have to exercise your stock options.”

    Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 9:00 ↗

    From Why Profits Interests Beat Stock Options in PE Equity Pools

    “A lot of times with stock options to take possession of the stock option to start what you call start the clock on capital gains treatment people actually have to write a check.”

    Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 9:08 ↗

    From Why Profits Interests Beat Stock Options in PE Equity Pools

  3. Internal deal terms undergo verification from outside industry peers

    Private equity sponsors know the exact answers to valuation mechanics. Executives cross-check internal equity illustration grids by taking the information to external investment bankers and other operators.

    “On my side of the table, I know the answers to all these questions…”

    Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 42:21 ↗

    From Spotting Red Flags in PE Equity Grids and Rollovers

    “Once you have that information then call your investment banking friends, call other executives, call other private equity firms and bounce it off them for a sanity check.”

    Ryan Milligan, Private Equity Funcast · September 2026 · Watch at 17:50 ↗

    From How to Stress-Test a PE Management Equity Grid

Key takeaways from these write-ups

Why a 1% Equity Pool Slice Yields Far Less Than Expected

  • Quoted management equity percentages (typically 0.25% to 2%) apply only to the residual common equity pool, never to total enterprise value.
  • Senior debt takes the first dollar of exit proceeds, followed by the sponsor's preferred equity and accrued return, before any common equity distributes.

Why Profits Interests Beat Stock Options in PE Equity Pools

  • Profits interests tied to LLC structures grant management pure upside in a sale without requiring an upfront cash check or out-of-pocket capital.
  • Stock options force executives to write personal checks to exercise and start the clock on long-term capital gains tax treatment.

How to Stress-Test a PE Management Equity Grid

  • Sponsors often present equity illustration grids with exit enterprise values that conceal aggressive operating assumptions.
  • Reverse-engineering the top row of an equity grid reveals the implied EBITDA and revenue multiples required to hit projected payouts.

Spotting Red Flags in PE Equity Grids and Rollovers

  • Sponsors who refuse to share detailed distribution waterfalls or financial models during hiring discussions are intentionally concealing downside economics.
  • Aggressive hurdle structures tied entirely to unrealistic performance multiples often leave management teams with zero incentive payout despite solid operational execution.

How we attribute quotes. Every quote was matched against the episode transcript, so the words and the timestamp are real (we trim filler words like "um", nothing else). The name comes from our written summary of the episode. YouTube gives us no voice-by-voice transcript, so open the timestamp to hear who is talking. See a wrong name? Tell us and we fix or remove it.

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