9 Horses for 9 Courses. One Race You Want to Win.

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Did you hear about a guy named Willie Mullins?

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He’s not a Wall Street investor or a Silicon Valley founder . He’s a horse trainer. But not just any trainer. Mullins is the most successful trainer in Cheltenham Festival history.

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Now, the Cheltenham Festival is no small deal. It’s the Olympics of jump racing. It’s where the best trainers, horses, and jockeys in the world gather every March. Winning there is like winning a gold medal, it defines your career.

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And Mullins hasn’t just won - he’s dominated. Since his first Festival win back in 1995, he’s racked up over 110 winners, including an astonishing 10 winners in a single Festival, a feat he’s achieved more than once. To put that in perspective, his closest rival, Nicky Henderson, has around 70 winners.

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How does he do it?

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By never betting on just one horse. He enters multiple horses in the same race - each with its own strengths, pace, and jockey. Some stumble, some sprint, some hold steady and but collectively, they maximise his chances of victory.

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Now, why am I telling you this? Because your wealth works the same way. You don’t win by betting everything on one ‘horse’ - one strategy, one investment, one tax play. You win by training a whole stable.

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The stable at a glance

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• Money Flow - the pace-setter.

• Emergency Reserves - the steady runner.

• Debt Strategy - the strategist.

• Concentration Risk - the balancer.

• Tax Positioning - the sprinter.

• Ownership Structures - the chess player.

• Income Protection - the shield.

• Asset Insurance - the defender.

• Estate & Family - the finisher.

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1) Understand Money Flow -The pace-setter

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Your cash flow operating system. It sets tempo so you’re not forced into reactive decisions. Last year I had a senior engineer on $480k total comp was “short” every month; a quick audit found $9,200/month of invisible spend (two overlapping health policies, unused subscriptions, food delivery drift). Another client sold $85k of RSUs at a dip to cover an ATO top-up they hadn’t pre-funded. That's pure timing pain caused by cash flow fog.

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How to train your horse?

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• Run a 60-day money map and tag every outflow as Fixed / Flexible / Fuel (Fuel = investments + tax set-asides).
   

• Build a bill-smoothing calendar (rates, insurance, rego, school fees) to avoid lump-sum shocks.
   

• Use separate bank buckets: everyday, tax/PAYG, investments, true emergencies.

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2) Establish Emergency Reserves -The steady runner

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Your shock absorber. Without it, markets and life choose your timing.

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A VP with zero buffer sold $120k of stock the same week the company missed earnings. That locked in losses and created extra tax. Another family faced a $13.2k roof replacement on investment property and a $3.1k dental bill in the same month; without reserves they carried a card balance at 19.99% for three months.

 

How to train your horse?

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• Target 6 months of core expenses (9–12 months if single-income with dependants).

• Park in a high-yield savings account that’s linked but out of sight.

• After any drawdown, auto-refill via a fixed % until back at target.

• Keep reserves separate from “opportunity cash” so investments don’t pretend to be safety.​

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3) Manage Debt Intelligently - The strategist

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Coordinate offsets, repayment order, and loan types to lower drag without starving growth. Last month I met A couple with P&I on an investment loan and cash idling in the wrong offset switched strategy and freed $30k/year in cash flow . Same income, better coordination. Another exec “snowballed” deductible debt first (felt tidy) while carrying $22k on a card at 19.99% — wrong horse, wrong lane.

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How to train your horse?

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• Classify good vs bad debt (deductible/productive vs high-rate/consumption).

• Align offsets and repayments with your tax position; don’t kill deductible debt while cash earns nothing.

• Sync lump sums to vesting calendars and bonus cycles.

• For property investors, avoid structure choices that accidentally kill deductions.

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4) Reduce Concentration Risk - The balancer

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Stops one ticker or sector from dictating your future. Your income and unvested equity already lean into your employer; your portfolio shouldn’t double down.

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I worked with a senior IC with $2m in employer stock saw a 45% drawdown in one season -on paper losses of $900k while their bonus was cut. Dual-tech couples often discover both careers and portfolios hinge on the same sector; a hiring freeze + price dip becomes a double hit.

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How to train your horse?

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• Set a single-stock ceiling (commonly 10–15% of net worth).

• Trim via pre-committed tranches (quarterly or into strength) to avoid second-guessing.

• Pre-allocate proceeds across index funds, super, property, cash buckets.

• Add simple if/then rules (e.g., “If weight ≥ 15%, sell to 10%”).
   

5) Optimise Tax Positioning -The sprinter

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Turns tax from penalty to performance. RSUs are typically income at vest; later gains fall under CGT. Timing and structures matter.

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3 months ago I worked with a $500k earner with quarterly vests faced a $180k tax bill; by timing sales, maximising concessional super and correcting ownership, we cut the effective hit by ~40%. Another client delayed a sale 11 months and missed the 50% CGT discount window. This was an avoidable bonus to the tax man!

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How to train your horse?

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• Build a vest & sell calendar to coordinate PAYG top-ups, CGT timing, and cash needs.

• Maximise concessional super (watch Division 293 thresholds; use catch-up caps if eligible).

• Use the right bucket (individual/trust/SMSF/company) when the 10-year math wins.

• Keep a tax reserve sized to your vest schedule, not last year’s guess.

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6) Configure Ownership Structures -The chess player

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Where assets live, who benefits, and how income flows - now and at exit. The right structure adds control, protection, and tax efficiency.

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A family trust streaming $60k to a lower-income spouse saved ~$18k in a single year (rate-dependent). An SMSF holding broad index exposure reduced portfolio tax drag while ring-fencing retirement assets. Conversely, one client put an IP in the wrong entity and wore higher land tax plus admin friction for years.

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How to train your horse?

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• Start with end-game objectives (income distribution, asset protection, succession).

• Model 10-year flows before setup; don’t “win” this year and lose the decade.

• Keep compliance disciplined (minutes, distributions, lodgements).

• Align super/insurance beneficiary nominations with your estate plan.

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7) Protect Your Income -The shield

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If you buy a new car, you insure it and get all bells and whistles. If a machine printed your salary would you insure it?

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Two staffers on $420k had very different outcomes: one with 90-day waiting / to age-65 benefit maintained contributions during treatment; the other, uncovered, sold stock at troughs and paused super for 18 months. Another common trap: policies with “any occupation” inside super are mostly CRAP and the definitions that don’t match tech roles.
 

How to train your horse?

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• Review waiting period, benefit period, and own-occupation definitions.

• Calibrate sums insured to actual obligations (debt, dependants, runway).

• Coordinate with employer benefits; consider TPD/trauma where appropriate.

• Re-check cover after role changes, pay jumps, or new debt.

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8) Insure Core Assets -The defender

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Protects what you’ve built on two fronts:

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1. Risk transfer (insurance) for events like fire, storms, rent default, liability claims.

2. Risk separation (structures) so creditors and predators can’t easily reach assets you intend to keep safe.

• Creditors = banks and claimants if something goes wrong (personal guarantees, business disputes, accidents).

• Predators = the wrong relationship dynamics, yours or your kids’. Think: you gift a deposit, your daughter marries, later her spouse walks away with 50% of the asset you funded.

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These are few examples I saw in my 20+ years of experience

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• A landlord without loss-of-rent cover wore an $18k vacancy/repair hit after a tenant issue.

• Another client discovered their home was 22% under-insured vs current rebuild costs after storms.

• Parents “gifted” $300k to help a child buy a property; two years later, separation proceedings treated the funds as joint property. A documented loan with a registered security interest would have given them a seat at the table to take back the property.

• An investment property held in personal names sat behind several director guarantees. When a business deal soured, creditors could target personal assets. Holding growth assets in an appropriate trust/SMSF ring-fences them (within rules), while keeping adequate insurance on the entity that owns them.

 

Training notes (how to train this horse):

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• Do the annual insurance audit: home, contents, landlord, vehicle, and public liability (plus professional/business cover if you contract).

• Update sum insured for today’s rebuild costs (materials/ labour) and real-world rent-default timelines.

• Align excesses with your emergency fund so a claim doesn’t force a sale elsewhere.

• Track renewal dates on one page; remove overlaps and plug gaps across policies and entities.

• Match the policyholder to the owner: the named insured on each policy must be the actual title holder (you, trust, company, SMSF) so claims pay correctly.

• Separate risk from wealth: keep operating/business risk in a company; hold long-term assets in a trust or SMSF (where appropriate) to reduce exposure to business creditors.

• Use loans, not gifts, to kids: if you’re helping with a deposit, document it as a secured loan (with a simple loan agreement and, where suitable, a registered interest). This preserves your position if relationships change.

• Consider a family trust for new investments: it can provide distribution flexibility, some protection from creditors, and cleaner estate planning—provided compliance is disciplined.

• Review personal guarantees you’ve signed (credit cards, leases, supplier agreements). Where possible, renegotiate or limit guarantees so they don’t trail your personal assets.

• Align estate and structure: ensure wills, super/life insurance nominations, and trust control (appointor/trustee) all point to the same intent—so assets don’t drift into the wrong hands at the worst time.9) Future-Proof Your Family -The finisher

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9) Future-Proof Your Family — the finisher

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Wills, enduring powers, guardianship, super nominations, and (where relevant) testamentary trusts. This turns assets into outcomes for the people you love — with less tax and friction.

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A couple still had pre-kids wills; with RSUs and property added, intestacy would’ve delayed and diluted outcomes. Updating to include testamentary trusts protected minors and enabled tax-effective distributions. Another case: non-binding super nominations sent benefits through the estate, creating delays and avoidable tax.

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How to train your horse?

 

• Refresh documents after every life/asset change (marriage, kids, property, equity windfalls).

• Consider testamentary trusts for minors or blended families.

• Maintain a secure “when it happens” file: key contacts, policies, passwords, instructions.

• Choose executors/attorneys who will actually do the job (and brief them).

 

Now, are you training your horses to win you race in all conditions?

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Track conditions (markets & life)

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No two races run on the same surface. Rates move. ATO settings shift. Teams “re-align.” Kids wake at 3 a.m. Parents need help. You change, too. The point isn’t to predict every patch of mud. It’s to train a stable that runs on firm or heavy going without panic so that you save on tax, make more money and retire earlier.

If you can't train your horses, its time for you to know what's the trainer job

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The trainer’s job

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The trainer's job is to condition the stable and stop the horses working against each other. I’ve seen smart people overpay the wrong loan, underfund tax, and carry 40% in one ticker because “it’ll bounce.” That’s not laziness. It’s misalignment.

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Twenty years in, across 360+ tech clients, the pattern is reliable: align the nine and compounding shows up where you can feel it . It takes tax down, risk down, progress up. No heroics. Just coordination.

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If you are not that trainer, maybe its time to get one to train and win across different track conditions

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Whenever you're ready, here are a few ways I can help you read on where you stand, the fastest levers to pull, and whether property is your engine or your anchor. No fluff. Just clarity.

 

1. Work 1:1 with me — build a strategic, work-optional financial plan.

2. Listen to my Podcast — real financial strategies for tech pros, no boring jargon.

3. The Wealth Byte Newsletter — quick, no-fluff emails twice a month.

4. Follow me on LinkedIn — over 3,000 tech pros already do.

5. Wealth Bytes - You Tube — bite-sized videos on investing, equity, tax strategies, and building real wealth.

 

P.s. Our advisory is operating at capacity, reflecting the tailored approach we provide. We’ll begin onboarding select new clients again from 10 November 2025.

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Personal Update

 

1. I am back to the gym. Midday to boost my day energy. Sleep struggles are less ( may be gym helped). anyways I feel better.

2. I joined a book club, it will force me to read more and I love it.

3. My biggest take away last month is a client I helped save $16,000 in mortgage repayment in 90 minutes. She was over the moon and it gave me shivers how I was able to help.