Inside Brookfield’s Trillion-Dollar Investing Playbook | Connor Teskey
- Guest
- Connor Teskey
- Read time
- ~5 min
- Uploaded
- 17 Mar 2026
- Duration
- 1:24:27
- Views
- 35.9K
KEYPOINTS
- 01
Brookfield invests in the ‘backbone of the global economy’—and that backbone keeps changing.
It raises money from the world’s largest pools of capital and deploys it across about 60 countries, mainly the U.S. and Western Europe. Teskey estimates two-thirds to 70% of what it invests in today wasn’t an investable asset class 15–20 years ago: hydro dams then, solar, nuclear and batteries now; ports and railroads then, plus data centres, fibre and towers now. Products grew from four a decade ago to about 60—flagship, mezzanine debt, super-core and retail-wealth versions of the same strategies.
- 02
If a deal feels 90% right, do it—and do ten of them.
His first Brookfield boss warned against the false precision of Excel; you must overlay judgment because the model only looks certain. Waiting to de-risk everything to the nth degree means you de-risk your deals and also do none. Being right nine times out of ten is really good.
- 03
Take execution and operating risk, never market risk.
For a solar farm the four drivers are construction cost, the power purchase agreement, the EPC (engineering, procurement and construction) contract and financing. Brookfield won’t put capital in the ground until all four are locked at once, so rates, power prices and inflation can move without hurting returns. The same template applies to build-to-suit real estate and data centres contracted with hyperscalers or sovereigns.
- 04
Underwrite the downside; let upside be a free option.
Investment committee time goes overwhelmingly on the worst case. Buy high-quality, market-leading businesses with downside protection, make the base case depend only on things you control, and accept asymmetric upside you don’t need. Deals are usually killed after diligence for two reasons: a weak revenue construct or counterparty, or too much construction risk for the return.
- 05
Finance asset by asset with non-recourse, long-term, fixed-rate debt, and hold excess liquidity.
It’s more work and not the cheapest, but one bad asset can’t taint a portfolio—and a great bid for one asset isn’t trapped in a shared facility. ‘Liquidity is overvalued when you don’t need it and incredibly undervalued when you do.’ Spare capital protects covenants and lets Brookfield buy when others can’t, which he calls one of its most enduring advantages.
- 06
AI infrastructure will be overbuilt—so only build against contracts in tier-one markets.
Data-centre deals have expanded on three compounding fronts: more centres, bigger centres, and investors now funding chips, servers, power, grid connection and substations, not just racks and shells. Counterparties are ‘almost undoubtedly the greatest companies of all time.’ Overbuild happens in every cycle, but Brookfield doesn’t build on spec and picks locations with multiple users so facilities can be re-contracted after 20 years.
- 07
Local autonomy to source and operate; central approval for every capital decision.
Each market has local investment, operating and fundraising teams. All deployment comes to a small central group, giving perspective: the best deal a region has seen in two years may lose to better risk-adjusted returns elsewhere. Committee isn’t a one-hour verdict; teams iterate for weeks and face a detailed ‘capital committee’ review three to four weeks before final approval.
- 08
Every return bridge includes operational improvement, rooted in 100 years as an owner-operator.
Founded around 1900, Brookfield spent its first century as an industrial conglomerate, and its balance sheet remains the largest investor in its own funds. Expertise mostly sits above portfolio companies; for turnarounds it inserts people. Global health-and-safety standards roll out immediately because those who get safety right tend to be the best long-term operators.
- 09
AI is boosting productivity more than cutting jobs across 500 portfolio companies.
Companies may trial any AI tool but must share what worked and what failed so 499 others benefit. Wins include pricing models and factory-floor redesign, plus predictive maintenance across nearly $1T of real assets—flagging a loose bolt on a machine not due for service for two years—and site-scanning phone apps listing safety risks for 300,000 operating staff. Robotics will arrive slower than expected but matter more.
- 10
The next growth wave is individual investors.
Brookfield targets $2T by 2030. Institutional allocations to alternatives should double in a decade, but the individual market—retail, high net worth, annuities, 401(k)s—is larger with almost no alternatives exposure. As index inclusion favours mega-caps, many mid-to-large companies are hard to own publicly.
EXAMPLES
- 01
Westinghouse: a downside bet that caught a nuclear revival.
Nuclear was out of favour, but Westinghouse was a critical supplier with a long tail and room for operational fixes. The base case worked on efficiency alone; then a global nuclear revitalisation delivered the upside.
- 02
Oaktree: from ‘it looks cheap’ to a strategic partnership.
Early in his career Teskey analysed a struggling alternatives manager and realised he could value it by first understanding Brookfield. In early 2018 he told Bruce Flatt that counter-cyclical Oaktree looked undervalued. Flatt asked what they could do strategically, given Brookfield’s thin credit exposure. They proposed buying out the public holders while partnering with founders, closing in 2019; Oaktree then grew sharply during COVID.
- 03
Moved to London and switched to renewables in 2016—told, not asked.
He had no particular desire to join renewables but said yes, joining a small team building a European platform. Working away from his boss forced initiative—no emailing to ask permission to send an email—and his ‘shooting percentage’ proved far higher than he feared.
- 04
The feedback that put him in a tailspin.
About 12–14 months in, without a modelling background, a mentor said his work was great but ‘nobody knows what you’re talking about’—his explanations were too complicated. Crushed overnight, he decided it was a gift: you must do the work and explain it.
- 05
A small Canadian cold-storage company was his favourite learning deal.
An underperforming business with simple value drivers, it became a fantastic investment and taught him the fundamentals.
OTHER RELEVANT
- 01
Hard work is also availability.
Teskey thinks people call him hardworking less for building models than for always making time—calls through airports and late at night for juniors and seniors seeking advice.
- 02
After a win, ask ‘what are we working on now?’
The non-Brookfield move is a three-week victory lap. They prize nerdy, intellectually curious people who tackle problems others failed at, work well in teams, and, like Flatt, care more about others’ success than credit.
- 03
Read materials before the meeting; skim headlines daily.
Reading a deck beforehand allows more thoughtful discussion than reading and listening at once. A daily digest of ~15 infrastructure headlines gives the direction of travel; he digs only into the relevant ones.
- 04
Children are the best prioritisation forcing function.
His two priorities—family and Brookfield—are ‘miles ahead of third place.’ After starting a family he found care isn’t finite; other things fell away and he can’t even name what they were.