brianmatthews retweetledi
brianmatthews
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brianmatthews retweetledi

Today, ProsperOps announced that they are being acquired by @flexera .
This is an incredible outcome for ProsperOps and a seminal moment for us at Active Capital.
ProsperOps has been a special company for me and our firm from the very beginning.
I worked with the founders for many years at @Rackspace. We weren’t especially close at the time, but I had deep respect for their work.
In 2018, after two of the founders left Rackspace, we met quietly in New Braunfels to talk through the idea of starting something new.
A few months later I led their pre-seed round at Active Capital.
I loved their vision. From my time in the cloud world, I knew how massive cloud spend was becoming and how painful cost optimization was for businesses.
Most tools at the time focused on reporting. ProsperOps had a very different idea: automate savings and optimization directly. Even before AI was fashionable, the company was built around automation, intelligence, and outcomes rather than dashboards.
From there, the company took off.
What stands out in hindsight is how intentionally ProsperOps was built. Under their leadership, this became one of the best-run companies I’ve been involved with. The culture was real and durable. You could see it in employee tenure, public sentiment, and consistent execution over time.
These guys built the company from first principles, and I have incredible respect for that. For example, the company started generating revenue quickly, and as growth accelerated, there was pressure to raise more capital. They resisted that. It simply wasn’t necessary.
In fact, ProsperOps never raised another venture round beyond our initial investment yet was always one of the fastest growing companies in our portfolio.
Then came early acquisition interest.
When you’re only a couple of years in and someone offers what feels like life-changing money, it’s hard to turn down. There was understandable temptation. But instead of selling early, we provided secondary capital so the founders could take some liquidity off the table and keep building.
I’m not sure how many pre-seed venture capital firms would do that.
But it changed everything.
By staying independent, ProsperOps continued to compound. Over time, the company became far more meaningful and far more valuable.
This is the biggest outcome for our firm to date. I feel incredibly proud and privileged to have been the lead investor alongside this team from the very beginning. Watching a group of former Rackers go on to build one of the most successful companies to come out of our ecosystem is something I’ll always be grateful for.
I want to specifically thank the three founders:
- Chris Cochran, an incredible leader and CEO.
- Erik Carlin, a product savant who could see around every corner. cc @ecarlin
- Chris Kuehl, whose technical vision was remarkable to watch play out at scale.
Congratulations to the ProsperOps team and to Flexera.
And thank you to everyone involved in the ProsperOps journey.
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brianmatthews retweetledi

@TheDentonDay Love Terry but he still has yet to put up a 1200 yard season. He’s good but not great.
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Trading 30-year-old Terry McLaurin because you don't want to pay him $30 mil per year for 31-year-old Tyreek Hill who's getting paid $30 mil per year and is a well known locker room disrupter would be legitimately awful.
#RaiseHail
NFL Rumors@nflrums
🚨🚨NFL RUMORS The #Dolphins and #Commanders reportedly have discussed a Terry McLaurin and Tyreek Hill TRADE
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@themannix Amazing no doubt. But you musta missed Vince Young?
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@benhubbard @themannix Ha watched it last night. Watching Christmas Vacation right now. I’d def say gremlins is a Christmas movie, released in summer.
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Is #DieHard a Christmas movie?
A Christmas Story was released in movie theaters on November 10, 1983.
National Lampoon's Christmas Vacation was released on December 1, 1983.
Home Alone was released November 16, 1990.
Elf was November 7, 2003.
The Night Before was November 20, 2015.
This list goes on, of Christmas movies and the release date being in November or December... in the Christmas holiday season.
Die Hard was released in 1988... in JULY.
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@brianmatthews @granthpaulsen 😂 and had the best weapons in the NFL But that's the narrative now. Winning used to be the standard, now it's regular season stats
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Jay Gruden on one change he would make if he was Kliff Kingsbury:
"I think he does a good job in the running game but I think some of his passing game, If I had any recommendations for him at all, it would be move Terry around a little bit. You can't always put him on the left. Use the word Buckeye [then] Noah Brown and Terry switch sides. It's not that hard. Line him up on the right side, put him to the field sometimes not to the boundary where your always on the left hash. The slant to Noah Brown, let Terry run that slant route and just say the word Buckeye and let Terry be the outside guy."
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@granthpaulsen @LordCommander50 You had me until Kirk Cousins. He’s produced a single postseason win. One.
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@LordCommander50 Kyle Shanahan - One of the best HCs in the NFL and considered the best offensive mind.
Kirk Cousins - A top 10 QB over the past 10 years in the NFL.
Yeah, crazy us.
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