kyle fritz

@markcecchini @TaxAlphaInsider Once caught a MS advisor telling a client who had equity comp administered by MS they HAD to work with them …

@TaxAlphaInsider YES So many hidden fees and conflicts that will never show up on a statement or quarterly report.

If you are about to go through a major IPO or tender offer: >> be very careful when you are offered "free consultations" from the advisors at the financial company where the equity is administered << 1) They don't know you. Odds are they won't go deep enough on the analysis needed to properly advise you in the context of YOUR overall finances. These are incredibly complex topics that spill over into almost every area of your life (tax, estate planning, charitable, investments, cash flow, etc) 2) They are being opportunistic. They are incentivized to have you liquidate the majority of your stock so that they can manage the proceeds for a fee. When Stripe had their big tender in 2023, MS advisors were blanketly telling people to "sell it all" (per internal Stripe Slack channel chatter) Stripe stock has increased by 200% since then. Seek objective, competent advice from someone who will get to know your situation intimately and has the tools to show you all the scenarios and tax implications before making recommendations. 3) They often give out false and/or misleading information. -"We're the only ones that can do ____ strategy." -"We have special relationships/discounts because of our relationship with your company." -"This is all free to you! We're just in it for the love of the game." -"Your staggered lockup % applies to ALL equity including options and unvested shares, not just vested equity" (^^this is the latest nonsense trickling through SPCX group chats that someone got direct from an advisor...like what are we doing here?). One again, be careful out there.

@markcecchini Preach it Mark!

Me: Long/short tax-aware is great for the right client in the right circumstances. Them: Yeah, but it’s complicated! Me: Sure. So is a 7-figure tax bill, ISOs, PPUs, QSBS, concentrated stock, and living with an 8-figure liquid net worth before age 40 Them: Yeah, but you're stuck with 1,000 positions and margin balance! Me: I’ve already unwound long/short back to long-only for multiple clients after a few years without triggering meaningful tax consequences. Them: Yeah, but it's just tax deferral, not tax savings! Me: We might need to educate you on the concept of time value of money....Tax deferral = money stays invested. Them: Yeah, but the fees and costs! Me: Margin interest is going to be partially tax-deductible. SMA fee is the cost of doing business, and it's less than the majority of mutual fund expense ratios. Them: Yeah, but the tracking error! Me: Sure. That's why we compare it to the actual objective: after-tax, after-fee, risk-adjusted returns vs the benchmark. Not “did it beat the S&P 500”. Them: Yeah, but the degradation of cost basis! Me: 351 exchanges, cherry-pick lot selection + DAF funding, strategic rebalancing, and eventually unwinding when the tradeoff changes. Naysayers man....

@T_Gatzemeier CRUTs, QOZs?

"What strategies are there to sell my company stock, without getting killed in taxes?" Here is your tax-efficient strategy stack... (Yes, there are some other strategies, but these 8 are pretty powerful.)

@AdviserCounsel I was thinking the same, why not hire folks as w-2 employees of a managed entity? I guess to much costs or friction

They could effectively stand up their own captive wealth management business for less than $100 million in recurring revenue and keep the profit for themselves.

@AdviserCounsel I’m surprised if any advisor was actually suprised by this

Imagine your custodian constantly assures you that they have no desire to compete with you to only turn around and begin to compete with you.

@MarketPalmer_ For those of us on the institutional side with Fidelity… I think there’s a lot of strong opinions…

Fidelity gets a ton of love – and for good reason. One of the most trustworthy investment platforms out there. But wow do they need a better user-interface.

@markcecchini Piece of mind for someone that is competent at what they do is worth every penny!

See what happened was you relentlessly focused on cost and completely ignored the potential for value extraction when you reframe the way you evaluate services, your life will change dramatically

The Definition of a Narcissist.

@TaxAlphaInsider 😂

Adviser selling to aggregator.

@MebFaber @Fidelity Go ask any RIA their experience with long short SMA’s with Fidelity….. lots of fun stories there

AHAHAHA, they actually did it. The cretins at @Fidelity are charging retail $100 commissions to trade 1 share of some ETFs. Gross.

@markcecchini Love QSBS stacking but it is complex, makes more sense the larger the estimated exit

Just got to see another QSBS “trust stacking” case up close This is when you transfer QSBS-eligible shares into 1 (or multiple) non-grantor trusts well before an exit each trust a separate QSBS-eligible entity if structured properly you = $10M Federal tax free cap gains trust 1 = $10M Federal tax free cap gains trust 2 = $10M Federal tax free cap gains ….etc ($15M each if the equity was acquired post 7/2025 with new OBBBA tax bill) The decision to fund these trusts is not one to be taken lightly The gifts are irrevocable and eat into your lifetime estate exemption You had to have a niche experienced attorney involved here Most founders don’t even know this exists

I’m not one of those advisors that doesn’t think AI will dramatically effect our industry but… I think we are still a ways off The level of accuracy by just how you a change a simple prompt can wildly change the answer. Folks need to be careful taking everything at face value

@MrFamilyOffice I think to much is lost on thought of what the tangible cost is of a family office in any form, having a team can bring so much soft benefit, really tough to state what it’s worth

@TKopelman The irony is im a financial planner and i think about hiring one for me and my wife every day lol It’s not always a sole skillset of knowledge but time

Reasons to hire a financial planner: - you own a business - you don't have time - you pay a lot in taxes - you have equity comp - your finances are complex - you do not want to do it yourself - you don't get done what needs to get done - you & your spouse can't get aligned on decisions - you are anxious & unsure you are doing the right things

@Budgetdog_ Hold on I thought you were a passive index dca guy?!

Since buying $META at essentially the literal bottom, it has outperformed $VOO by 22% on an average annualized basis 🤯 Small asymmetric risk-reward bets once wealthy is a game changer.

But expectations need to be established of these strategies actually provide

I think the most important thing for a retail investors to understand is that nearly all tax strategies are a DEFERRAL MECHANISM At the end of the day almost everything is not tax free, just kicking the can down the road which candidly in most situations is still great

@TaxAlphaInsider To heirs*

@TaxAlphaInsider Get both estate exclusion and losses to offset distribution heirs 🤫

I have a bunch of memes I never ship... here's a random one from a year ago that seems especially relevant as long/short heats up. Investors are increasingly wondering whether the manager's alpha can cover higher fees, financing, and trading costs.