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Orlando Bravo Profile
Orlando Bravo

@OrlandoBravoTB

39,863
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Following
99
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790
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Co-founder of @ThomaBravo and @BravoFamilyFdn . Opinions are my own.

Miami, FL
Joined April 2013
Don't wanna be here? Send us removal request.
@OrlandoBravoTB
Orlando Bravo
2 years
As much as I respect & admire @WarrenBuffett , I don’t understand why he hangs on to the idea that #Bitcoin is not money because money is what the govt says it is. He’s leaving out something more important than the govt — money is what people in the free market say it is.
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@OrlandoBravoTB
Orlando Bravo
3 years
If your job title has a “C” on it - you don’t complain. Your role is to resolve issues, not create them.
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@OrlandoBravoTB
Orlando Bravo
3 years
I look at #BTC price as quarterly average — a beauty. HODL
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@OrlandoBravoTB
Orlando Bravo
3 years
I was taught in business school that pessimists make the best investors. I've found the opposite to be true. Pessimists waste creative time making up negative stories, while optimists are busy imagining the possibilities. And yes, one can be optimistic, cautious, and diligent.
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@OrlandoBravoTB
Orlando Bravo
3 years
I was asked today how I could defend #Bitcoin since Sweden's DG said it should be banned due to ESG. I said mining needs to move to use clean energy. In the meantime, DG should ban all banking since it emits 20x more carbon than #BTC .
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@OrlandoBravoTB
Orlando Bravo
3 years
Just read a Wall St strategist piece on #crypto . Author begins, “I dont have a valuation model to apply to #BTC ”…then ends, “I’d take another look if crypto valuations plummeted to deeply distressed values.” How w/o a valuation framework, can one know what a distressed value is?
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@OrlandoBravoTB
Orlando Bravo
2 years
Tech cos built in the last decade were built in an environment where capital was free. Most of these cos have been structured in a way that they’ll always lose money — and most won’t be able to change. There will be a lot of orphan software public cos in the near future.
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@OrlandoBravoTB
Orlando Bravo
2 years
It has always been about FCF. Now everyone finally believes it.
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@OrlandoBravoTB
Orlando Bravo
2 years
Powerful case study from Elon’s acquisition of Twitter: 1. If you’ve decided not to partner w existing mgmt, make leadership change immediately (no “transitions”). 2. If restructuring is needed, start Day 1 (no “180 day plans” or yearlong “consulting studies” that go nowhere).
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@OrlandoBravoTB
Orlando Bravo
3 years
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@OrlandoBravoTB
Orlando Bravo
2 years
As a young investor then, I had to work hard to forget the 1998 and 1999 valuation frameworks and multiples. The faster investors realize it’s back to basics now, the better off they will be.
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@OrlandoBravoTB
Orlando Bravo
2 years
A few years from now, the next group of exiting software IPOs will likely be companies that have come out of this with 40% cash flow margins and sustainable growth.
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@OrlandoBravoTB
Orlando Bravo
3 years
You will achieve better results by focusing most of your hard work on further building your strengths rather than on trying to improve your weaknesses. And you will probably be happier during the process as well
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@OrlandoBravoTB
Orlando Bravo
3 years
If I showed you a business with nearly 100% recurring revs, 120% net retention, 90% GM & thousands of customers that can’t function w/o the product — would you think that’s a “risky asset?” The market does because it’s “tech.”
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@OrlandoBravoTB
Orlando Bravo
2 years
Software cos should be profitable relatively early on. Those that “need” to continue to lose money in order to grow are fundamentally not worth very much.
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@OrlandoBravoTB
Orlando Bravo
2 years
When your competitor overspends on Sales & Marketing, you may want to thank them for using their resources to develop a bigger market opportunity for you.
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@OrlandoBravoTB
Orlando Bravo
3 years
The young VC investors I meet are mainly interested in working in #crypto deals. This is one of the many reasons why I believe #Web3 will continue to thrive. It's where the capital will be going.
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@OrlandoBravoTB
Orlando Bravo
3 years
Regulators now saying that crypto should be held to the same standard as a bank deposit?? Banks take all kinds of risks with people's deposits (without their consent) in order to profit. What does this bank structure have anything to do with buying and holding crypto?
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@OrlandoBravoTB
Orlando Bravo
2 years
It's not just a bear market — it’s back to the time when companies are valued on after-tax free cash flow. Build but build profitably.
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@OrlandoBravoTB
Orlando Bravo
3 years
In 1994, I moved to the Bay Area to be a part of the tech boom. Earlier this year, I moved to #Miami to be a part of the #web3 movement -- and help expose more of the Latinx community to tech. When I look out at the skyline I see huge possibilities. @FrancisSuarez
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@OrlandoBravoTB
Orlando Bravo
2 years
Astonishing the number of private companies that continue to try to buy their way to growth instead of focusing on building a real business.
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@OrlandoBravoTB
Orlando Bravo
2 years
It’s ok to borrow to buy a company or real estate as you have somewhat control of cash flow produced to service debt, and you don't get called on the mark. But I wouldn’t borrow to buy a security — your collateral is purely subject to what others think it is worth.
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@OrlandoBravoTB
Orlando Bravo
3 years
“Retail investors are reckless and don’t understand fundamental investing.” Hedge fund managers investing $250MM in a Series E after 10 minutes of due diligence:
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@OrlandoBravoTB
Orlando Bravo
3 years
@APompliano Superbad. There is no better character than McLovin
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@OrlandoBravoTB
Orlando Bravo
2 years
Fundamental investors don’t buy stories — they buy numbers.
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@OrlandoBravoTB
Orlando Bravo
3 years
A year ago, we decided to move some of our #SF team to #Miami — great decision. Next up, we’re going to be recruiting undergrads from @univmiami . Let’s goooo!!! @FrancisSuarez
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@OrlandoBravoTB
Orlando Bravo
3 years
In investing, diversification is way overrated. Focus on really understanding what you are looking to buy. I don’t know anyone who is an “expert” in all the companies and industries in a “diversified” portfolio.
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@OrlandoBravoTB
Orlando Bravo
2 years
LBO is the new (and better) IPO.
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@OrlandoBravoTB
Orlando Bravo
3 years
Liquidity is overrated. If you have so much conviction in the manager you chose or in the companies that you own a piece of -- why would you place so much value in the ability to get out at every instant?
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@OrlandoBravoTB
Orlando Bravo
2 years
Excess equity hurts cos just as much as excess debt does as it discourages execs from measuring, building great processes, making careful investment decisions and overall building profitable businesses. Many of these cos end up in restructurings as well.
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@OrlandoBravoTB
Orlando Bravo
2 years
The inv style of just buying the best product in a large TAM, paying big ARR multiples for cos with very high burn rates, valuations based on “long-term margin targets,” and a world where every subsequent round had to be an up round…All that is over
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@OrlandoBravoTB
Orlando Bravo
3 years
Right on budget
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@OrlandoBravoTB
Orlando Bravo
2 years
Instead of spending your time trying to figure out where the overall economy is headed (which is impossible) — spend your time figuring out what companies will perform well in any economic environment.
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@OrlandoBravoTB
Orlando Bravo
3 years
The best use case is usually the simplest one. One of the many reasons why I love #Bitcoin . While all other layer 1 networks are competing for a more complex use case, #BTC stands tall as the ultimate store of value.
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@OrlandoBravoTB
Orlando Bravo
2 years
Over the past 10 years, investors in software have been buying at a revenue multiple, justified by a long term margin assumption. That long term has come — it is today.
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@OrlandoBravoTB
Orlando Bravo
10 months
When we take unprofitable software cos private, we often find a lack of clear strategy & alignment. A focus on the bottom line has so many organizational benefits — it’s a powerful tool to get everyone aligned on a few strategic principles & drive cross-functional collaboration.
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@OrlandoBravoTB
Orlando Bravo
3 years
Don’t make the popular decision…make the right one.
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@OrlandoBravoTB
Orlando Bravo
3 years
Do u think unprofitable/high growth soft cos are way down because: 1. Investors r applying a higher disc rate to cash flows that r far out? OR 2. Investors r finally realizing that, for many of these cos, cfl will never materialize in the future?
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@OrlandoBravoTB
Orlando Bravo
2 years
When looking at an investment, if one of your top considerations is how you’ll get liquidity on it — it likely means you don't have enough conviction in the company & you’re probably better off passing. Great businesses ultimately provide many liquidity paths.
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@OrlandoBravoTB
Orlando Bravo
2 years
Bankers who only know how to sell companies through auctions and “competitive tension” will get nowhere in this market. While bankers who know how to work with the right buyer to get to the right price will end up delivering a lot of value to their clients.
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@OrlandoBravoTB
Orlando Bravo
2 years
2023….lets gooooooo!!!!
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@OrlandoBravoTB
Orlando Bravo
3 years
For too long, investors have rewarded cos for growth/TAM w little attention to profits. As a result, so many soft cos have been organized in a way that they now produce massive losses. This will be difficult to reverse & is a real problem for the industry.
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@OrlandoBravoTB
Orlando Bravo
3 years
Buffett termed retail inv as the “casino group” and said “you cant build a society around it.” I think the opposite - active retail inv brings all society into an xchange of ideas that ultimately inspire the creation of new bus models. You dont learn anything by buying the S&P
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@OrlandoBravoTB
Orlando Bravo
2 years
Focus on buying quality. Quality of revs, earnings, business model, market, leadership and culture. You will appreciate that even more in a recession.
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@OrlandoBravoTB
Orlando Bravo
3 years
Cash flow is always in season
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@OrlandoBravoTB
Orlando Bravo
2 years
In this market, I wouldn’t look at a company's “takeover value” as part of one’s investment thesis or to try to predict a bottom on a stock. Neither strategics nor PE have the time & money to pursue even a fraction of the attractive M&A opportunities that exist right now.
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@OrlandoBravoTB
Orlando Bravo
3 years
Whoever still thinks PE is about leverage and cost cutting is stuck in the 80s.
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@OrlandoBravoTB
Orlando Bravo
3 years
Great execs know how to run companies. Great VCs know how to invest in companies. Operators thinking they can be great VCs is just as bad as when VCs think they can be great operators.
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@OrlandoBravoTB
Orlando Bravo
2 years
This downturn has been telegraphed for nearly a year now. It’s almost certain that bookings will be challenged over the foreseeable quarters. Cos have had plenty of notice & time to reduce expenses in anticipation of this. Mgmt saying “they were surprised” is not a viable excuse.
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@OrlandoBravoTB
Orlando Bravo
3 years
Going public always sounds great and exciting…until mgmt teams become trapped by the “beat and raise” game that Wall St demands they play.
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@OrlandoBravoTB
Orlando Bravo
2 years
I’ve never met a CEO who regretted going private. And those that had the courage to do so have ended up delivering big premiums to today’s prices for their public shareholders. And, by going private, they’ve focused on profitable growth — putting their cos in a much better place.
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@OrlandoBravoTB
Orlando Bravo
3 years
Was going to buy into layer 1 network just when found out they r doing a private deal at big discount. Less than inspiring, so bought more #BTC instead. I'm OK w private rds as long as terms are disclosed. U have a moral obligation to do so as lots of people r trading on ur quote
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@OrlandoBravoTB
Orlando Bravo
3 years
Why are people still comparing Bitcoin to gold? The value of #Bitcoin is the value of a whole new financial system... And anyway, who buys gold anymore? And for those that do - I hope they don't admit it... at least not in public. #BTC
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@OrlandoBravoTB
Orlando Bravo
2 years
In the process of revaluing unprofitable software cos, investors may have lost sight of the fact that digital transformation is only in its infancy. Cos that focus on execution and become highly profitable can then spend time reminding investors of the big opportunity.
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@OrlandoBravoTB
Orlando Bravo
2 years
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@OrlandoBravoTB
Orlando Bravo
2 years
Inflation caused by a ~$4T fiscal stimulus (26% of US GDP), has a compounding effect in increasing income inequality. Excuses are a disservice to the most vulnerable. We need responsible fiscal policy & bolder monetary policy with policies that encourage innovation & free trade.
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@OrlandoBravoTB
Orlando Bravo
2 years
@litcapital My favorite is when he says, “it excludes interest, without replacing it with new debt”????
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@OrlandoBravoTB
Orlando Bravo
2 years
Over the last decade, the SAS industry went largely unmanaged. Except for a few great ones, most of these cos are now poised to produce remarkable losses (with bookings slowing and FX headwinds). For innovations at these companies to survive, the industry has to be restructured.
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@OrlandoBravoTB
Orlando Bravo
2 years
It amazes me how tech cos' get really worried about their ability to give debtholders a 3% aft-tax return but are so confident they can give equity a 30% return.
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@OrlandoBravoTB
Orlando Bravo
2 years
Getting ready to give the Commencement talk at @Stanford to the @StanfordGSB Class of 2020. The graduates will soon fill the seats to celebrate and have a long overdue in-person ceremony. Lets gooo!!!
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@OrlandoBravoTB
Orlando Bravo
2 years
Turn the page quickly, so you can focus on what matters most — building the business and growing the top line.
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@OrlandoBravoTB
Orlando Bravo
2 years
Founders are better off focusing less on valuation and more on building a business model that eliminates the need for dilution altogether
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@OrlandoBravoTB
Orlando Bravo
3 years
You will become a much better investor, decision-maker and leader once you acknowledge that much of your past success is the result of being in the right place at the right time.
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@OrlandoBravoTB
Orlando Bravo
3 years
Spend the first 25 years of your career learning from your mentors and the next 25 learning from the next generation.
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@OrlandoBravoTB
Orlando Bravo
1 year
Going public used to not be very attractive to PE as 1. You lose control of your Balance Sheet to do M&A and 2. mgmt starts playing a different game (the beat & raise game and stock comp incentives). But now, with 13% cost of debt and public shareholders wanting cos run for
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@OrlandoBravoTB
Orlando Bravo
2 years
The tech community way underestimates all you can do with your company when you generate lots of free cash flow.
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@OrlandoBravoTB
Orlando Bravo
3 years
Really enjoyed our conversation, @patrick_oshag . Thanks for having me.
@patrick_oshag
Patrick OShaughnessy
3 years
My conversation with @OrlandoBravoTB We discuss: - software margins - sources of return - what it means to be a market leader - operating excellence - short holding periods, when to sell - decentralization I learned a ton from Orlando Enjoy!
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@OrlandoBravoTB
Orlando Bravo
3 years
When we were looking to pursue control software deals 20 yrs ago, my VC friends would say "those co's are old and will go out of business" and my PE friends would say "tech is too risky." Don't worry about the external validation -- focus on the fundamentals of the business.
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@OrlandoBravoTB
Orlando Bravo
2 years
The Rule of 40 is so mediocre
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@OrlandoBravoTB
Orlando Bravo
2 years
Over the past yr, entrepreneurs have gotten every signal that they must build real profitable cos vs buying growth (rev multiples crashed, less capital avail, cash positions in question). They all hear this — but only the great cos are willing to make radical operational changes.
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@OrlandoBravoTB
Orlando Bravo
2 years
Bitcoin breaks up governments’ monopoly over money. Competition is a very good thing for society. Looking forward to discussing this at #Bitcoin2022 tomorrow. #Bitcoin
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@OrlandoBravoTB
Orlando Bravo
1 year
Strategics are now ahead of PE in engaging in M&A when the macro is uncertain. It’s usually the other way around. But this time, PE is obsessing about the macro while strategics are experiencing a pretty solid business environment.
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@OrlandoBravoTB
Orlando Bravo
3 years
When you are running a negative P&L and your growth slows or market sentiment changes, your valuation floor is likely to be a lot lower than you think.
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@OrlandoBravoTB
Orlando Bravo
1 year
The PE comp model for portco execs is designed to reward superior performance at a much higher rate than the public co comp model. The public co comp model is excellent at rewarding mediocre performance. The best leaders get this and self-select to PE cos.
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@OrlandoBravoTB
Orlando Bravo
2 years
Be wary of an investment thesis based on buying “cheap”— a subsequent decline in valuations can quickly make that thesis invalid.
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@OrlandoBravoTB
Orlando Bravo
3 years
A European LP just called me so fired up! He's visiting #Miami & loved the city's energy and #VC community. @FrancisSuarez has been so smart in inventing this growing ecosystem & creating positive change during a pandemic. This is just the beginning. #artbaselmiami let's gooo!!!!
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@OrlandoBravoTB
Orlando Bravo
3 years
Hard to focus on anything as we helplessly watch the human tragedy unfolding in Ukraine. At the same time, we are witnessing amazing leadership by President Zelensky matched by the courageous actions of Ukrainian citizens.
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@OrlandoBravoTB
Orlando Bravo
2 years
For those who celebrate it, wishing you an amazing Christmas Eve full of love and joy with your family and friends. Happy holidays!
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@OrlandoBravoTB
Orlando Bravo
3 years
The amount of talent that’s been developed internally is often the best indicator of how strong the org’s leaders are.
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@OrlandoBravoTB
Orlando Bravo
2 years
Over the last decade, many investors mischaracterized wasteful spending by cos as "investments in growth." Those investors are unlikely to repeat that mistake for some time. Mgmt teams that adjust and focus on profitable growth will be the ones rewarded going forward.
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@OrlandoBravoTB
Orlando Bravo
2 years
The rerating from revenue to EBITDA multiples continues to accelerate.
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@OrlandoBravoTB
Orlando Bravo
2 years
In the near future, one of the first dd items a buyer is likely to ask for is to see how stable a co’s cfl was during the downturn. Mgmt’s current actions to protect the bottom line will likely have material implications on the future multiple that buyers will be willing to pay.
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@OrlandoBravoTB
Orlando Bravo
2 years
Best way to figure out how your investment is doing - just look at the effective UFCF multiple that you own it at. There is no hiding from that.
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@OrlandoBravoTB
Orlando Bravo
2 years
Excited to partner with @Coupa ’s management team and employees.
@thomabravo
Thoma Bravo
2 years
. @Coupa Software, $COUP, a leader in Business Spend Management, has entered into a definitive agreement to be acquired by Thoma Bravo in an all-cash transaction valued at $8 billion. Learn more:
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@OrlandoBravoTB
Orlando Bravo
3 years
An optimistic mindset will enable you to see so many great opportunities in whatever is dealt to you
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@OrlandoBravoTB
Orlando Bravo
3 years
A large established PE manager told me that he was uncomfortable doing deals remotely without "meeting in person." I told him that I love doing remote deals because if I like my potential CEO partner on zoom, I will like her or him that much more in person.
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@OrlandoBravoTB
Orlando Bravo
2 years
Happy Mother’s Day!!!!!
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@OrlandoBravoTB
Orlando Bravo
2 years
My dad spent so much time with me growing up and taught me work ethic, good values and integrity — all by example. Happy Father’s Day to all the amazing dads out there leading by example.
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@OrlandoBravoTB
Orlando Bravo
2 years
Software companies tend to panic when there is a slowdown. It should be ok as long as you accept the fact that there will be a lower level of business for some time and you adjust your resources accordingly.
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@OrlandoBravoTB
Orlando Bravo
2 years
. @elonmusk is proving that he can have a bigger influence on the platform by engaging on it rather than being on its Board of Directors. What a brilliant move all around.
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@OrlandoBravoTB
Orlando Bravo
3 years
It really is time to start focusing on co’s burn rates
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@OrlandoBravoTB
Orlando Bravo
3 years
Careers are built not by the plans you make but by taking the opportunities that are thrust upon you.
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@OrlandoBravoTB
Orlando Bravo
2 years
Those that try to use aggressive tactics to buy a public co from a Board & Mgmt that doesn't want to sell create a lot of drama and, in the end, mostly end up wasting their time. Putting in the effort to build relationships over time is a much better approach.
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@OrlandoBravoTB
Orlando Bravo
3 years
@APompliano
Anthony Pompliano 🌪
3 years
Wow. The City of Miami just announced they are going to give a Bitcoin dividend to every citizen that sets up a digital wallet. “We’re going to be the first city in America to give a bitcoin yield as a dividend directly to its residents." - @FrancisSuarez This is incredible.
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@OrlandoBravoTB
Orlando Bravo
3 years
Nothing makes you a more disciplined buyer than undergoing the experience of having to sell assets.
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@OrlandoBravoTB
Orlando Bravo
3 years
Investing styles come from experiences. For me, it was the ‘00 bubble burst. I never wanted to go thru that again, so we built an investment model centered on recurring revs, operations & combining growth with cfl. This market will help shape a new generation of investors.
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@OrlandoBravoTB
Orlando Bravo
3 years
We’ll look back and say, “Can you believe there was a big premium for losing money?”
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@OrlandoBravoTB
Orlando Bravo
2 years
The key to operations is simplification. The best operators are routinely looking to simplify everything from products to processes to pricing.
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@OrlandoBravoTB
Orlando Bravo
2 years
Refreshing to see big tech cos focused on operational efficiency. Over time, they will prove that the more efficient (and profitable) a co is — the faster it will grow. Startups and developing cos should really take note and follow.
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