Extend & Pretend Cowboy @Cashflow_Cowboy Twitter profile

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Longing for a simpler era when fintwit spent more time doing things like roasting Softbank's investment in WeWork.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

@patrick_oshag

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Adopted this handsome fellow today. Thinking about a rename since he’s pretty young. Will try to keep the pup content down to only maximum cuteness.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Anyone else getting bored with the industrial, reclaimed wood, modern farmhouse design aesthetic? What's going to be the new, new thing?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Hello other family office, we should collaborate together as we are also a family office. 5 minutes later: Here's an opportunity to invest in our 2 & 20 SPV

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Extend & Pretend Cowboy

@Cashflow_Cowboy

7 months

@Carnage4Life Would love to know more about how an outsider became CEO. Seems like the type of org where that should have never happened

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Spotted in the wild, a CA transplant telling us they’re a real estate investor without telling us they’re real estate investor.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

You know you’re in Texas when these are the vehicles out in front of a fancy hotel

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 months

Family office conference relationship building: Hello family office person, I too am a family office person. Great to meet you. I do X. Oh you do Y. We don't do much of that. Dinner and drinks ensue. Let's stay in touch to collaborate. Never communicate with each other again

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Career regret for the younger ones to consider. I wish I spent more time meeting people working in/on interesting businesses and less time networking with other investors. Investor network is valuable, but I think I would have more to offer with a more diverse network.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

For those that care, last year I left family office life to join a fund focused on investing in companies. I still aspire to put out content to share experiences and observations on family office life that I believe will be relevant along with whatever else comes up.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Relocating to Austin before the end of the year. Who are good people on here in that town?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

@default_friend From @EvilMopacATX

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 months

@ebitdaddy90 Firm with long standing culture of promoting within hires from the outside for the first time and it’s always a McKinsey product. Every. Damn. Time.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

A productive Saturday afternoon with some of Austin twitter’s finest.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

When considering RE deals from a LP perspective, I wish I paid more attention to insurance costs and taxes in the underwriting assumptions earlier in my career. You can spend a bunch of time thinking about the top-line only for these items to erode your distributions.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Being treated like dumb money by a wide swath of people can be a draining aspect of working for a family office. I think the general FO reputation regarding sophistication (or lack there of) is generally well deserved, but dealing with that attitude gets frustrating.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Recently had a FO tell me they looked back at how their direct PE deals did vs how their PE funds performed and found the funds to be better performers. Concluded they should just do funds given their staff size. Direct is hard. Make sure you have the staff to do it if you do.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

You either run out of good content or live long enough to see yourself become a shit poster.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

I love animals. Damn does it hurt to say goodbye to a beloved pet. Our family had an expected loss of a young, sweet pet today. Love the little fur balls. Miss the little buddy too much already.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

New post up. A look at the 2019 UBS Family Office Report. Highlights were pulled out and discussed for those of you who haven't read the whole things.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Had a conversation with a young person in their mid 20s interested in PE/VC. He seemed shook when I disabused him of the notion the investment industry was a place where firms were well run, adding value to all of their investments, and that board meetings got stuff done

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Is there any phrase in investing more overrated, overused, and often wrong than 'proprietary deal flow'?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Tweet number 1k. Really enjoying the community around here. To mark the occasion, feel free to ask me your questions about family offices. I'll do my best to answer, but likely won't be able to address everything given the unique dynamics of each organization and my own exp.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Figured I would try the meme thing. New family office investment team gets their marching orders. How it Started: How it's Going:

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Current status: High school friends call me 'Citadel Shill'.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

A family office decides to try direct venture. This is a fictional cautionary tale. To begin, a small equity pre-seed/seed investment is made through a principal’s relationship. The round is led by an angel small or fund. Little diligence is done because of the small check size.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Adventure

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

The search continues for actual 'proprietary deal flow'.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Been hearing $meta no longer taking the space at 6th and Gaud in Austin. They were set to take all 33 floors of office space. Earnings call mentioned the company right sizing their office footprint. Building still under construction.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Finally got around to writing another post for the blog. I lay out some reasons why one would bother to build an investing family office.

Why an Investing Family Office?

Today’s post is inspired by interactions on twitter over a period of several months. Given the opaque nature of many Family Offices (“FOs”), there are questions by some about why principals bother …

cowboy-investing.com

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

There are some strange small companies out there that are better businesses than you would expect.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

When the CFA renewal email hits your inbox.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Starting a thread with all of the Austin activity. To start a little context on growth. MSA been growing ~60K annually starting in 2014. Only the 28th largest US MSA. Over next decade could pass Pittsburgh, Sacramento, and Portland. Longer term could catch St Louis & Baltimore.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Heavily leaning toward starting a blog on family office investing with an emphasis on direct investing. Any sense on how often I need to publish content to generate enough interest. First topic would be on VC investing and the silly expectations FOs have for doing it direct.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

My general feeling is family offices that describe themselves as opportunistic don’t have a strategy or strong sense of who they are.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

I'm skeptical that more than a small minority of FOs will develop any kind of competence in direct venture investing. The pain of the j-curve will shake out many. Staff skill mismatches and principals chasing the new hotness are also impediments.

Family offices become serious rivals to VC firms for funding start-ups

Investors that may have previously confined themselves to public markets are now clomping all over the venture capital landscape

www.ft.com

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

This weekend Austin will be a delightful mix of the global mega wealthy F1 apparatus, locals that enjoy the event, people recently into F1 due to the Netflix documentary, and Texas NASCAR fans. Welcome and enjoy for those that will be in town.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Started getting active about meeting people from finance twitter in person over the last two months and generally have had experiences that exceeded my expectations. Good people out there. Still not enough wrestling gifs though.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Family offices that have a top executive that's more of a friend/confidant to the principal than a true professional can be tough places for people that take their careers seriously.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Family offices that say they want to do more direct deals when you actually send direct deals their way.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Had to call around to six doggy day cares to get a spot booked for the pup (non holiday weekend). The only one that was even taking new clients was out of town a bit. Some weren’t even taking waitlist clients. Might be a small biz op. Anyone know economics on these businesses?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

A flyover town HQed bank buying SVB feels like a fitting representation of the vibes shift

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

@deepfates Chattanooga, TN one I didn’t see yet that deserves mention. Greenville, SC as well.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Had a boss with a legal background who always counseled to never put anything in writing you would be concerned about defending in a deposition or be afraid of it becoming public through some kind of legal discovery. Also don't be an ass hole.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

For several years, seems like the popular take from family offices was we're 12-18 months from a recession and we're building liquidity and taking less risk. How many actually get aggressive investing through the current environment now that recession seems nigh?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Secondaries and private credit appear to be the new hotness in the family office content circuit. Proceed accordingly.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Family office jobs are both great and terrible places to learn. Great because there are a wide variety of opportunities to review. Terrible because internal processes tend not to control the chaos and going from macro, to RE, to credit, to VC can make your head spin.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Gm from Austin

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

A Covid skill I worked on. Ready to go for tomorrow in the morning.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

11 months

Quick holiday story. I was driving yesterday to visit my family for the Thanksgiving and saw a lonely dog looking confused and getting a bit too close to the interstate. I pulled over to see if she was just a lost pup and a stranger did the same. She was very nervous but warmed

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

A good reminder after one of the most exhausting, disappointing, and frustrating weeks I can remember, that you can get out and find new energy, renewal, and restoration.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Considering a career change. Curious on perspectives and thoughts from people who left investing to do something else.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Chicago is undefeated in making me put on weight.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

MSD Partners doing new things. Setting up to take outside money for a private equity strategy. Wouldn't be surprised to see more of the bigger, institutionalized FOs evolve in this way.

MSD Partners, Backed by Michael Dell’s Family Office, Preps for Outside Investors

The firm is preparing for a new set of investors as it plans to raise a private-equity vehicle, which will include a significant investment from firm employees and the Dell family.

www.wsj.com

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Interviewing tip for those transitioning to a FO career path. The goal is to get in, titles are overrated. Know of a candidate who made final rounds for a very well funded FO team. (1/6)

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Family offices to get more opportunities to pass on direct deals while claiming they want to be more active with direct investing.

Family Offices Get Greater Access to Private Company Trades

A network of more than 400 family offices and a venture backed by hedge fund billionaire Paul Tudor Jones are partnering to help simplify deal-making for the ultra-wealthy.

www.bloomberg.com

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Digging through the owner's expenses in small businesses can be one of the more entertaining part of due diligence. Impressive how much they can spend on meals, cars, entertainment, payments to other entities for 'services', ex-spouse expenses, etc.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

New UBS Family Office report is out. Check out the link for the report. Will aim to get a post up hitting the highlights by end of the month. The love fest for private equity continues.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Signs of market excess that stuck with me from the last few years. - Stadium naming rights by younger companies - Have fun staying poor - Lambos at conferences - Private markets for retail advocates - 1 year fund deployment cycles - 100x rev - Everyone has a syndicate

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Current count of family office conferences attended that I thought were valuable: 0

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Great time riding Vail with @mstillwell8 , who is a spectacular mountain guide. Fun discussions of business and life along with conquering chutes across the mountain. Highly recommend.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Not surprised that Florida received the largest increase in gross income from migration since 2020, but I am surprised at the magnitude of the gain relative to other no income tax states (particularly Texas given the population size).

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Balance. Breckenridge for inquiring minds.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Recently passed the 5k follower mark. Really enjoyed the connections made on here and optimistic about future relationships yet to be formed. I would encourage people to be open enough to engage with and meet people in their online communities here. Cheers everyone.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

PE firms buying and selling the same companies from each other.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

What is the most interesting, thoughtful, creative, crazy, or weird type of investment/strategy you've seen or heard of a family office pulling off that a typical fund can't/won't do?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Small town or burbs breakfast spots >>> city breakfast spots.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

When a partner at an accounting firm tells you they have all the resources in house to help with your family office's tax needs.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

‘Merica

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Associates at growth equity firms sending outreach emails to the CEO of a SaaS business that's about to hit $10M of ARR.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Had a 30 minute conversation with a family member about how well they're doing investing in SPACs. They also asked about trading options. That and my Robinhood day trading friends don't want to talk about the risks. Also their performance continues to be better than mine.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

1/ The last few months I've had conversations with several young people in the first 1-3 years of IB who are considering a move to venture capital/growth investing. Based on what they've been looking for in an organization, I've recommended they look at joining a young business.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Just had @HeimBBQ for lunch with @willis_cap in Fort Worth. I need a nap. Shout out to @fortworthchris for the recommendation.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

10 months

Closing out 2023 on a high note

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Family office staff staring down the horde of bankers, wealth managers, service providers, etc. when a liquidity event for your principal gets out.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

@mr_skilling Natural resources should be renamed defense against the dark arts. You'll see some of the best of the best in tomfoolery, poor management, shareholder abuse, misaligned incentives, and general griftiness.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

'Opportunistic' family office investment strategy in action.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

8 months

This would explain so much

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

My life has heavy ties to current boomtowns Austin, Denver, and Nashville. Watching them change and grow makes me wish we had more styles of regional architecture. The new stuff is all starting to look the same with a few exceptions.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

In family office world, odds are your principal(s) are going to make decisions that will be in conflict with the careers of their staff, even putting jobs at risk, for personal reasons. Part of the game. You have to get used to it or maybe this isn't the right place for you.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

BBQ meets breakfast has under explored food possibilities.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

So the new bank rescue playbook is for the SIFIs to make deposits at a struggling bank using the money they got from new customer deposits due to people trying to flee said bank?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

Reminder that many family offices are less liquid than you would imagine. Especially in challenged and uncertain market environments. Those that actually have liquidity can set up great partnerships, if they are actually out there you know, doing their jobs.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

A reminder to all those weeping for the non-accredited investors' lack of access to venture capital and how it impairs their ability to build wealth, the Nasdaq public market equivalent has done better than the venture asset class since the tech bubble. Need access to the best.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

When you move from a colder state to Texas and see people wearing winter coats when its 55 degrees outside.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Long Austin single family residential.

San Francisco Chronicle

@sfchronicle

3 years

Residents and city leaders are searching for answers: should they tolerate burglaries as a part of city living, and focus on barricading homes? Should repeat offenders get rehabilitation services, or be incarcerated so they can’t commit more crimes?

2K

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

In my experience, many family offices believe they need to worry more about vetting ideas instead of finding ideas. They would probably be better at diligence and have a better feel for good deals if they put more resources into finding potential investments and partners.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

4 years

White Claw nation, there are better ways to handle summer. Cc @moseskagan @lucas_irl_ @ccchaircut

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Extend & Pretend Cowboy

@Cashflow_Cowboy

10 months

Anyone else around here skeptical of anons that show up on the scene and immediately roll out a ton of baity threads to build up a fast audience? Seems like this playbook is more prevalent now. End game is suspect to me

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Venture GP trying to explain why they deployed a whole fund in six months during 2021

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

Investors who buy businesses or provide growth capital to companies that haven't had formalized boards should take the time in advance of the first board meeting to outline what responsibilities lie with the board vs what management can do on their own. (1/3)

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Been in an extended career/life funk, but catching up with @tsludwig yesterday was great for uplifting the spirits. A reminder the community on here can be great. Have had plenty of support from too many others on here to directly thank everyone without an obnoxious thread.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Reminder to people in or considering FO life and those that have or are targeting FOs as capital partners: investing regime changes can happen suddenly based on the desires of the principal with little notice. Caught up with a friend at shop currently going through a big shakeup.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

5 years

2019 UBS Family Office Report is out. Will have to follow up with some tweets about the nuggets found within when I get the time.

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Why are you lucky enough to see that deal?

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Extend & Pretend Cowboy

@Cashflow_Cowboy

7 months

@netcapgirl

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Extend & Pretend Cowboy

@Cashflow_Cowboy

2 years

Always another mid/late 20s former IB analyst starting a company aiming to get retail type investors access to private markets under the 'democratizing private equity' banner

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Extend & Pretend Cowboy

@Cashflow_Cowboy

3 years

Austin, we really doing this?

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