
How Brent Beshore Transformed 15 Companies Through Self Mastery
What this covers
Brent Beshore transformed from a controlling, achievement-driven entrepreneur to a relationship-focused business leader who now owns 15 companies. In this profound conversation, he reveals how personal growth and understanding of relationships changed everything — from his marriage to his business approach. Learn why most small business acquisitions fail, how to identify what truly matters in business decisions, and why treating companies as stewardships rather than possessions leads to better outcomes. This rare glimpse into both personal and business evolution offers wisdom for entrepreneurs at any stage.
00:00 - Intro 00:54 - Why Brent examined his life 04:50 - How Brent "fixed" his relationships 15:10 - How helping hurts 27:19 - How Brent was subtly controlling relationships 35:42 - Why Brent stopped drinking (mostly) 45:35 - How to run a business with love yet competitively 55:40 - Win-win relationships 01:00:40 - On debt 01:14:34 - On incentives 01:24:14 - How to hire and fire CEOs 01:29:24 - What most people miss about hiring 01:39:25 - Brent's playbook for taking over a company 01:46:26 - On projections 01:50:58 - Revisiting investments 01:53:50 - How "hands-off" is Brent? 02:03:40 - Where people go wrong in private equity 02:09:13 - On success
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Brent Beshore argues that sustainable success in business and life requires operating from love and abundance rather than fear and scarcity, which fundamentally changes how you treat people, make decisions, and build organizations—and this shift from self-protection to stewardship produces better long-term outcomes than traditional competitive models.
- Fear-driven behavior creates hero-victim dynamics that damage relationships and organizations, while abundance mindset enables genuine win-win outcomes
- Stewardship mentality—viewing oneself as custodian rather than owner—naturally aligns incentives across all stakeholders and eliminates short-termism
- Operational excellence and financial returns improve when people are treated with dignity and given agency, as demonstrated by the pandemic case study
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Patience fundamentally changes outcomes; playing long-term games with long-term time horizons leads to different decisions, behaviors, and sustainable advantage, whereas short-term thinking creates behaviors that feel justified in the moment but produce worse outcomes.
“the lack of patience changes the outcome and so when you lever up to get your your immediate returns and then you're like sort of like playing with house money uh you can sort of justify almost any behavior and when you think longterm like a family thinks of a business”
Warren Buffett's statement that 'price is my due diligence' is a useful heuristic because the higher the price you pay, the more things have to go right and the smaller your margin of safety; conversely, lower prices give you the ability to absorb mistakes and challenges.
“I um had the privilege of spending some time with Buffett at one point and I asked him this like battery of questions and he kind of I think at some point got frustrated with me um being I was probably being annoying and he said price is my due diligence and it was kind of like the the showstopper like drop the mic moment he was like because I was asking him all kinds of like how do you think about this or how do you think about that and timately he like I use price as my major due diligence filter which I thought was brilliant it's like this simple heris like the higher the price you pay for it the more you're pricing it to Perfection the more things have to go right the lower the the more you can absorb things”
Debt is not a source of return; it is an amplifier of returns. It makes good returns great and bad returns devastating. The appropriate amount of debt depends on how predictable and certain you are about future outcomes—high certainty allows more debt, but most businesses face unknowable futures, making high leverage a form of hubris.
“debt is not a source of return it is an amplifier of return so it makes good things be great it can take mediocre things and Destroy them and of course it takes bad things and nukes them the the higher your confidence in the predictability of the future the more debt you can use I say can use not should use”
Alcohol is one of the biggest inhibitors of testosterone in men, and testosterone's primary function is to make hard things seem easy; therefore, reducing or eliminating alcohol consumption directly improves a man's ability to handle challenges and perform difficult tasks.
“alcohol is one of uh in men especially one of the biggest Inhibitors of testosterone and we think of testosterone as like the libido you know hormone or whatever and it is but like that's not the the point like I wasn't like I was like oh well I'm you know drinking I was basically drinking almost every day and I was drinking a lot”
Physical health and mental health are deeply interconnected through the embodied nature of human existence; when physical health improves through consistent exercise, mental health, emotional capacity, and relational ability improve alongside it.
“the Greeks had this very like it's like body versus Soul like dualistic view like we are embodied creatures like we are one and the same that's not the proper view like our physical health impacts our mental health and vice versa right um and so I've I've seen this like wonderful like I have more energy to play with my children and the relationships are better”
All investing at the end of the day is the assumption of risk; the ideal investment scenario is you are assuming a risk that is knowable, you are being paid more to assume that risk, and you have some ability to mitigate that risk.
“all investing at the end of the day is the Assumption of risk the ideal investment scenario is you are assuming a risk that is knowable you are being paid more to assume that risk and you have some ability to mitigate that risk”
The private equity industry's traditional 2-and-20 fee model with 10-year fund lifecycles creates misaligned incentives where the operator (fund) benefits from gathering more capital (pushing toward larger deals and faster exits) and short holding periods (2-3 years), while this doesn't serve the LPs, the operating businesses, or the employees.
“the 2 and20 model right so on the amount of capital that you have either gotten to invest or have invested depending on the terms of the agreement with your uh limited partners you get a 2% fee uh annually that goes to covering your overhead costs and expenses of operations of the firm the seeking out the doing of the deals the um the oversight and governance post close and then you once you pay them back with a return typically um 6 to 8% maybe 10% depending on the situation then you get to share in the upsides”
Early in Berkshire Hathaway's history, Warren Buffett was actively involved in operating troublesome acquired businesses because they didn't work passively; he required management depth (like Harry Bottle at Dempster Mill) to fix operational issues, proving that even Buffett engaged actively in small business operations.
“Buffett was invested in sandborn maps and dimster Mill those are the two primary Investments I think this represented 70 or 75% of the assets of the buffet partnership one of the things that Buffett Ander connected very early on about was struggling businesses was struggles he was having with those two businesses um you know the story I think it's been told a number of times but is you know not often remembered because where they are now there's been like five seasons of Burkshire”
Fear-driven motivation produces faster short-term results and can achieve high excellence, but it is ultimately unsustainable because it comes with internal costs (stress, health degradation, relational damage) that eventually destroy the system, whereas love-based motivation is slower initially but compounds sustainably over time.
“dirty fuel is a for me uh I'd learned through my life to be it's it's it's a more potent fuel in the short term for me like I I get more stuff done quicker and usually even sometimes with higher Excellence out of dirty fuel than I do clean fuel that fear is a heck ofe almost higher o the problem is it's got all kinds of contaminants in it and you eventually like torch yourself and the car breaks down and you go off the rails and blow yourself up”
The act of giving without knowing the recipient's actual needs, even with good intentions, can harm people by removing their dignity and agency—the giver's emotional payoff and self-image can obscure the second and third-order consequences of well-meaning generosity.
“I had taken away the Dignity of those families and yeah they couldn't buy their kids Christmas gifts they were going to do something for them whatever they could do for them and instead like any kid you you give a kid a present kid like amazing you know but then it started asking all kinds of questions well why can't you buy me that present do you not love me why do these other people care more for me than you do”
Shame and fear in an individual create patterns of self-protection and control in relationships that, while often disguised as generosity or care, actually remove agency from others and create hero-victim dynamics that are deeply damaging to authentic connection.
“Heroes create victims because you're removing all agency from them and you are telling them that they can't help themselves that they are helpless and when you do that you are creating somebody who who is diminished and insulted”
The Enneagram framework identifies nine different personality types with distinct core fears and motivations; understanding your type helps you recognize your automatic defensive patterns and underlying insecurities that drive behavior.
“the other one that I've really enjoyed as inag because it it really shows you what is your underlying insecurity and what are your primary drives so there's nine numbers and each one has a very different set of pluses and minuses strengths and weaknesses”
Awareness of personal faults without accompanying healing is worse than remaining unaware, creating acute suffering as you become acutely conscious of your brokenness and its impact on others while lacking the tools to address it.
“when you go from denial to um awareness um it's it's actually way worse so like the awareness of your faults and awareness of your shortcomings without the healing of those is actually put you in a far worse position”
Creating a strong identity around a habit (e.g., 'I am a person who works out every day' rather than 'I should try to work out') removes the element of choice and makes the behavior automatic and sustainable, whereas willpower-based approaches dependent on motivation are fragile.
“you said well I just work out every day it's part of my identity I don't have a choice if I'm going to work out I just have a choice what I do and I remember it hit me like a ton of bricks I was like oh my gosh yeah you're right”
Real friendship requires bidirectional exchange of need and support; if one person is always helping and the other always receiving, it creates a power imbalance that prevents authentic relationship and eventually builds resentment even if neither party consciously recognizes it.
“there's no way to have a real relationship with somebody unless it's bidirectional it can't be you helping somebody and never needing help because then again it's the exact same principle you're creating sort of a a hero victim Dynamics the power dynamics in any relationship are super”
The way you think about loving others determines your relationship quality: loving people the way you want to be loved is really self-love; loving them the way they 'should' want to be loved is prescriptive; the only approach that works is asking them how they want to be loved and meeting them there.
“in my marriage and in my friendships in my relationship with my children to some degree like I used to try to love them uh the way I wanted to be loved and that doesn't work very well because really what you're doing is you're loving yourself by doing that and then I kind of went through a phase where I was like okay well I'm going love them the way they should want to be loved M that doesn't work well either why don't they love it why don't they love it right and then I started really being like okay I'm going to pretend like I have no preconceived notions of how somebody wants to be loved and just gon to ask them”
Being nice (smoothing over conflict to maintain comfort) is different from being kind (helping someone move into a better role or out of a role they're failing in); Permanent Equity has erred toward being nice when they should have been kind, which hasn't served people or companies well.
“we've screwed up being kind to somebody is saying hey I think you're in the wrong role and they're stressed out their lives are not they're not enjoying life they're not enjoying their role they're fear-based right”
Even when you intellectually understand love-based principles and even when you give grace to others for their transactional offers, you still feel a 'Spidey sense' (protective instinct) when someone acts from scarcity, which triggers your own defensive scarcity response, and the key is recognizing this pattern without judgment.
“I have this like it's like a weird feeling that rises up in me it's like a uh like I don't know Spidey s right it's that I think it's like a protective thing where you're like okay I can feel myself rising in in competitiveness rising in scarcity to meet their scarcity”
There are fundamentally only two ways to live: out of fear (which is scarce, competitive, and focused on self-protection) or out of genuine love and care for others and oneself, and all other behaviors rise from one of these two bases.
“there are really only two ways to live you're going to live out of fear or you're going to live out of genuine love and care for others and love and care for yourself and like that's it like everything else Rises between those two”
Internal processors can isolate and think through problems alone, while external processors need someone to externally process with or they'll create inappropriate relationships with subordinates; understanding this difference matters for CEO support structures.
“we try to understand for our CEOs if they're internal or external processors that's a really important piece if you're a CEO as an internal processor then you can you can go away with your thoughts and be fine if you're an external processor and you're the CEO you have no one to external process with or you end up creating inappropriate relationships with people who work for you”
When hiring and managing people, understanding their personality type (Myers-Briggs, Enneagram, etc.) through multiple lenses is critical because it allows you to predict behavior, create empathy, and avoid assuming everyone operates the way you do—personality testing should be used to create 3D understanding of people, not to put them in boxes.
“I've really become much more familiar with different personality testing and um specifically like I I you know I've looked at a bunch of them I really like the combination of Myers Briggs and inag if you think think about our business as um you know we we take money and we turn it into more money I think you miss the most important thing that we really do which is our whole business is predicated on predicting the behaviors of people like if we can predict the behaviors of people there's no way to lose”
Running a business is more difficult than outsiders imagine; operating a portfolio of multiple businesses requires scaling your infrastructure repeatedly, each time going back to near-zero and reinvesting all free cash flow, which creates a 'gauntlet' that many firms fail to navigate.
“It's a miracle that permanent Equity has 15 companies it's a miracle it's a miracle that we have a team that for the most part loves each other and cares about each other and wants to do good things like it's a literally not a day goes by when I don't think it's a miracle and by the way the future is not secure like we might screw up badly and so there's always work to be done there's no free lunch nothing's e easy”
The pool builder case study demonstrates a counterintuitive business model: this business appeared to be a capital-intensive construction business (unfavorable) but was actually a capital-light marketing and logistics business (favorable) with 97% direct-to-consumer revenue and minimal capex, mispriced because others categorized it wrongly.
“I was expecting it to be you know 10% or 15% it was 97% and then I said oh interesting like what is your capex Capital expenditures on an annual basis and it was like microscopic I was like weird tiny capex good free cash flow direct to Consumer man that's a really durable business”
Most of the businesses Permanent Equity targets are 'mispriced' opportunities—either misunderstood, information-asymmetric, or perceived as risky for reasons the firm can mitigate—and identifying the specific moat and understanding what's holding the business back is how they correlate risk to price.
“we are um describing the what I would call the overall situation of the business um who are they what business are they in how does it work we we also think about like what is the core action of the business so often times things our favorite deals are ones that look weird or different on the surface there may be a little furry fuzzy things on the deal or they're misunderstood and hence the price and the connection between the the price and the value is is is off right so we're trying to look for mispriced opportunities”
Operating from competitive and transactional dynamics, even when it produces external success, eventually leads to burnout and relational failure; the competitive model is incompatible with genuine relationship because 'competitiveness is the antithesis of relationship.'
“competitiveness is the opposite of relationship it is the antithesis of relationship like when we're competitive with somebody it's I win and you lose that's horrible especially when you're you're you're dealing with like my profession doesn't have to be competitive when I go out and play tennis or pickle ball with somebody like I don't have to win but before I had to win because I'm a winner winners win”
All small businesses are 'loosely functioning disasters' because people are messy; when you get multiple people together, the mess compounds exponentially. Therefore, buying a small business without debt provides optionality and adaptability to handle the inevitable chaos, whereas debt removes optionality.
“all businesses are Loosely functioning disasters like whether it's a not for-profit or for-profit or government institution like people are messy when you get multiple people together that mess compounds when you get large groups together groups together that mess compounds even further it's exponential”
The aeronautical business they bought in fall 2019 with no debt became dramatically more valuable through the pandemic because they had optionality to hire, buy distressed inventory at fire-sale prices, build systems, and implement new technology while competitors with debt were constrained in every way.
“we bought an aerospace business in the fall of 2019 I don't know if you know this Shane but Aerospace never goes down it's always flat or goes up we were told by by some of the people advising us on that deal they were like are you guys did you guys get dropped on your head as a child or something like you're not putting any debt on an aerospace business”
There are three basic conflict patterns that people follow: move against (force submission, confrontation), move toward (appeasement, avoiding conflict), and move away (isolation). Most people have a consistent order in which they default to these patterns, and recognizing your own pattern is useful for managing conflict.
“conflict pattern is something that I uh really have enjoyed studying um so we all have three basic Moves In conflict um and and actually if you watch these it's it's fun like now it's like a whenever I engage in Conflict I like I know my pattern and I very much know my wife's pattern and uh I I like I try to guess then other what other people's patterns are you can watch people like go through these phases but there's a uh it's called move against which is like no you're wrong screw you I want to like make you submit to me right”
After closing a business, problems are opportunities; the ideal approach is to assume little growth and underwrite the business with no trajectory change, because most attempts to dramatically change an operating business fail and it's hubristic to assume you can rapidly transform a business that's been operating a certain way for decades.
“after close like all the problems are merely opportunities I try to remind our team of this all the time because you get in these operating situations there's a lot going on like sometimes relationships are very strange there's weird power dynamics Dynamics all this stuff's going on and I I say to them yeah it's hard but this is what we get paid to do like we're in the business of Shaving fur”
People who haven't directly operated a business tend to be overconfident about how easy it is to transform businesses; those who have actually tried to change operating businesses learn that it's brutally difficult and that most grand transformation plans fail against the reality of managing actual people.
“this is often the dominant Narrative of people who haven't done it right so people who haven't actually been in the weeds who haven't bought a business who haven't tried to change it is like this is super simple you buy things for cheap huge amount of upside you go in and you transform them these guys are idiots yeah yeah these guys are idiots they don't know what they're doing it's like dude yeah you may have been to Harvard you may be well educated that guy's been working in the business for 30 years do you not think that he knows everything you know and far more mhm of course not”
Most people underestimate how much internal rationalization and justification occurs for their behavior; everyone acts rationally from their own perspective in the moment (e.g., heroin addicts choosing a hit), so understanding why requires asking why rather than judging.
“everyone acts rationally in the Moment Like This is the like the heroin addict who's choosing heroin over eating a meal or you know leaving their family in that moment believes they're doing the right thing for them believes it's rational to pursue that hit versus do everything else so the question you have to ask yourself is why”
A key signal for whether a potential business relationship will be win-win or not is apparent in the first offer or request: if it doesn't come across as fair, it's predictive that the relationship will require constant work to achieve win-win, or may not be winnable.
“often I find that the first request by somebody is very telling or the first offer here's what we want here's what we need from you and if that doesn't come across as Fair it's like the biggest signal in the world that it's like oh this is probably not a relationship that is going to be win-win I'm going to have to work to try to make it win-win but you've you've given me this valuable piece of information on day one without even intentionally doing so”
Asking someone for help is fundamentally different from always providing help—both patterns maintain unequal power dynamics, but many people (particularly high-achievers) struggle with asking for help because it feels like admitting weakness or losing control.
“when's the last time you asked somebody for help uh this morning I'm asking I'm I'm learning this is a new learned behavior though um CU in all the years I've known you this is like this is different recently yeah this is different I uh yeah I would I would always be the one who would be eager to help but rarely ask for help and again that that that destroys relationships”
The 'bladder problem' in business describes how excess cash on a balance sheet often gets spent wastefully on non-productive kingdom-building activities; wise businesses therefore reinvest high-return opportunities or return cash to shareholders rather than accumulating it.
“I call the bladder problem right the more money you have the more likely you're going to piss it away yeah this is where you see these businesses being run in ways that you're like they are they are murdering money they are destroying Capital”
Permanent Equity's alternative fee model—taking no management fees or reimbursements, only a percentage of free cash flow as it's returned—creates perfect alignment because the firm only benefits when capital is actually returned and all stakeholders (LPs, operators, firm) benefit from the same outcomes.
“we take no fees of any kind no reimbursements of any kind from the portfolio companies or from our LPS we get a percentage of free cash flow as we return cash back that's how we share with our with our investors Well turns out what that does for us is it gives us the perfectly aligned ability to if there are high return high probability projects to reinvest in the portfolio we would be idiots not to take the cash defer gratification and reinvest it”
Stewardship is a different mentality than ownership; stewards are custodians responsible for maintaining and improving something entrusted to them, whereas owners can extract value however they choose—this distinction fundamentally changes decision-making and leads to better long-term outcomes.
“Big shift for me was becoming a steward right it's this idea of stewardship and not ownership so the way I look at it as families are entrusting us to be stewards of their company it's a responsibility that we have yes we get benefits from being a steward yes we get to share in the fruits of the labor and progress of the company but at the end of the day my job is to make sure that these businesses you know remain intact are healthy”
Being asked how you want to be loved is the magic question that unlocks tremendous intimacy because most people don't actually know how they want to be loved and haven't thought about it, and the answer usually surprises them when they say it out loud.
“one of the questions I love asking my kids now is what do I do when you feel most loved and I really try to focus on doing those things for them um um that's sort of the magic question that unlocks a tremendous amount of intimacy with anyone really any friendship if you ask that same question you you'd be shocked and I think what the answers you get because in my marriage and in my friendships”
The most significant investment edge for Permanent Equity comes from their ability to predict human behavior through personality frameworks and understanding what actually drives people's decisions, not from market analysis or financial engineering.
“if we can predict the behaviors of people there's no way to lose and when we don't predict the behaviors of people we're almost certain to lose like it increased in incredible volatility into the system”
Permanent Equity's strategy is to buy 51-70% of businesses and explicitly not allow non-strategic actors—the remaining ownership must be held by people actively engaged in the business, which aligns incentives and prevents financial engineering.
“we don't allow non strategic actors yeah we want people who are actively engaged in the business to own the remainder”
Everything is relative; people can only assess their own circumstances against what they have been exposed to, so you may feel your marriage is successful when compared to other marriages you've observed, but that feeling changes completely once you're exposed to what is actually possible in a healthy relationship.
“Everything's Relative so like world class is the best you've ever seen you know you ask somebody who's only eating at fast food what's their favorite restaurant in the world they're going to tell you a fast food restaurant right um so you know the question we have to ask ourselves is like what do we have to compare it to”
Money amplifies your existing character—if you operate from fear and scarcity before wealth, wealth will make you more fearful and scarce; if you operate from abundance and love, wealth will amplify that. Money doesn't change your fundamental orientation; it reveals and magnifies it.
“money makes you more of what you already are right and so if you look at people with tremendous amount of resources who made that money through scarcity and through high competition and through uh stepping on people on the way up when they get to the top they continue to exhibit that behavior”
The Peter Principle (people rising beyond their abilities) is magnified in organizations because people cling to their titles and positions even when they're failing, due to pride and identity being rooted in position—humility and willingness to step down are extremely rare.
“careers often die by Suicide not by homicide like it's not I've watched this tragedy happen which is the Peter Principle someone Rises and they rise beyond their abilities and then they can't take a step back they're their pride their ego they their identity is rooted now in their title in their position”
Approximately 80% of small businesses are knowingly or unknowingly breaking regulatory rules because compliance is extremely complex (federal, state, and local regulations often conflict); identifying and fixing legal compliance is one of the first things Permanent Equity prioritizes post-close.
“my guess is 80% of the small businesses out there are are either knowingly or should know that they're breaking some sort of rules there's a lot of government regulation depending on the state you're in and often by the way Federal Regulation State regulation and local regulation will often times conflict with one another”