Brendan Keegan
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Articles by Brendan Keegan
The Simple Test to Use Early in Your Career That Pays Off for Decades
Before any big decision, ask: Will my future self thank me for this, or pay for it? Key Takeaways There is a difference between enjoying your youth and destroying your future, and most people don't see it until they are well past it. I think about that difference often, as an executive evaluating young leaders and as a father and mentor to founders who are just starting out. The boundary it describes is hard to see, and most people don't notice it until they are well past it.
The Simple Test to Use Early in Your Career That Pays Off for Decades
Brendan Keegan Fri, October 9, 2026 at 12:00 PM EDT 5 min read Add Yahoo as a preferred source to see more of our stories on Google. Add Yahoo on Google Vladimir Vladimirov | Getty Images Entrepreneur Media LLC and Yahoo Finance LLC may earn commission or revenue on some products and services through the links below. Key Takeaways Careers rarely split on one big decision. They split on small daily choices that compound over 20 years.
Forbes JAPAN 公式サイト（フォーブス ジャパン）
これは、私がこれまで取り入れてきた中で最も直感に反するリーダーシップの原則かもしれない。なぜなら、リーダーとしての私たちの本能は、往々にして正反対の方向に向かうからだ。 この本能のせいで、私たちは他人に厳しくなってしまう。すぐに他者を評価し、即座に批判し、彼らがどうすべきだったかを決めつける。その一方で、自分に対しては寛大になりがちだ。言い訳に終始し、自己正当化を並べ立て、自分の置かれた状況を深く思いやる。 しかし、この力関係を逆転させることができれば、劇的な変化をもたらすことができる。 リーダーシップの責任における「認知バイアス」を克服する 大半の人の行動パターンを見てみるといい。彼らは他人に完璧さを求める一方で、自分自身の不完全さは容認する。同僚が締め切りに遅れると厳しく非難するが、自分が遅れたときにはもっともな理由がある。部下がミスを犯せば注意力が足りないとし、自分がミスをすれば状況が困難だったと言い訳する。パートナーが何かを忘れると配慮が足りないとし、自分が忘れると手一杯だったと釈明する。...
How Mediocrity Quietly Creeps In — and How to Hold High Standards That Protect Your Profits and Culture
Opinions expressed by Entrepreneur contributors are their own. Many leaders see high standards purely as a tool for achievement, whether that means gaining a competitive edge or outperforming the market. For years, I saw them that way too, judging my organizations mostly by execution and output. But working in multiple executive roles has taught me something deeper: High standards are fundamentally a form of protection.
How To Hold Yourself Accountable As A Leader
Brendan P. Keegan is Chairman & CEO of bFEARLESS Ventures and is a 6-time CEO, 23-time board director and 3-time best-selling author. This might be the most counterintuitive leadership principle I’ve ever adopted. Because as leaders, our natural instinct tends to run in the opposite direction. This instinct makes us stricter with others: quick to judge, fast to criticize and certain about what they should have done differently.
Forbes JAPAN 公式サイト（フォーブス ジャパン）
ブレンダン・P・キーガンは、bFEARLESS Venturesの会長兼CEOであり、これまでに6度CEOを務め、23社の取締役を歴任、ベストセラー著書を3冊執筆している。 現代のコミュニケーション指標は、仕事上の成果に多大な影響を与えてきた。実際、企業経営の進化の過程のどこかで、目標達成の真の目的が、個人の深い実体験から「周囲にどう見せるか」という外見へとシフトしていくのを私たちは目の当たりにしてきた。 言い換えれば、リーダーは節目を、頂点に立つことで得られる戦略的な明晰さではなく、自分がそこに到達したことを他者にどれほど説得力をもって示せるかで評価するようになっている。この逆転現象は、深刻な経営上のリスクをもたらす。組織の真の追求を単なるパフォーマンスに変え、本質的な成長を戦術的なステータス・シグナリング（地位の誇示）へと変質させてしまうからだ。 私は、この行動上の罠を認識することが、戦略的な集中を取り戻したいと考えるすべてのエグゼクティブにとって不可欠だと考えている。 「外部の承認」と「観客の罠」...
5 Hidden Speed Bumps That Keep Good Companies From Becoming Great
Entrepreneur Media LLC and Yahoo Finance LLC may earn commission or revenue on some products and services through the links below. • Chasing your "fair share" of the market is a comfort trap that guarantees mediocrity — real growth comes from defining your company by the unmet needs of your clients, not the boundaries of your industry.
5 Hidden Speed Bumps That Keep Good Companies From Becoming Great
Opinions expressed by Entrepreneur contributors are their own. If you watch a NASCAR race, you’ll see a tight pack of cars traveling at 200 miles per hour, rubbing paint, turning left and fighting over inches of asphalt. To the casual observer, it looks like intense, cutthroat competition. But in the business world, a dangerous parallel occurs when every company mirrors its competitors’ offerings, operates on identical terms and chases the same core customers.
Beyond Status Signaling: Intrinsic Value In Executive Achievement
Brendan P. Keegan is Chairman & CEO of bFEARLESS Ventures and is a 6-time CEO, 23-time board director and 3-time best-selling author. Modern communication metrics have had a significant impact on professional achievement. In fact, somewhere along the evolution of corporate execution, we have witnessed the true intent of accomplishment shift from deep personal experience to public appearance.
Asset or Liability? One Question to Ask Before Buying Any Luxury Car
When you buy with the exit mapped out, passion doesn’t have to bleed capital. Most guys walk onto a showroom floor, look at the window sticker and ask the wrong question: What does this cost? That’s the classic consumer trap. In high-end automotive, if you start at the sticker price, you’ve already lost—because a sticker only tells you what someone wants today, not what the market will pay tomorrow.
Why Leaders Break Under Pressure — and How Pre-Built Decision Frameworks Prevent It Original
Opinions expressed by Entrepreneur contributors are their own. Every day, the internet is flooded with “leadership experts” dispensing cryptic advice to millions of followers. Most of them have never managed a complex P&L, built a team from scratch or fielded a 2 a.m. crisis call affecting hundreds of livelihoods. Their wisdom stays generic because it has never been stress-tested. They speak fluently in frameworks because they have never been forced to execute. But critique is cheap. Execution is not.
We Were Driving To Close Our IPO When It Was Pulled — Here’s How I Helped Save The Deal And Close A $40 Million Gap Overnight
Every stakeholder involved in the transaction faced a choice. Accept a smaller piece of the economics or watch the deal collapse entirely. When viewed through that lens, the numbers began to move. The two largest institutional investors increased their commitments by $10 million. The investment bank reduced its fee by $10 million, recognizing that a completed transaction was worth far more than a breakup fee.
We Were Driving To Close Our IPO When It Was Pulled — Here’s How I Helped Save The Deal And Close A $40 Million Gap Overnight
Opinions expressed by Entrepreneur contributors are their own. 30 cities. 12 days. Two weeks aboard a Gulfstream with our chairman, CFO and investment banking team on a global roadshow that seemed all but complete. The models had been built and stress-tested long before we landed in New York for the final meeting. Investors were engaged. Demand was strong. People were already talking about the closing dinner as if the deal was done.
Why high performance demands strategic sacrifice
Listen to this ArticleMore info The public narrative surrounding elite success is often incomplete. When people discuss high-profile leaders and their companies, the conversation centers on the wins, the remarkable innovations, and the market leadership being accomplished. These outcomes are celebrated because they are visible.
Forbes JAPAN 公式サイト（フォーブス ジャパン）
ブレンダン・P・キーガン氏はbFEARLESS Venturesの会長兼CEOであり、6度のCEO経験、23回の取締役就任、3度のベストセラー作家という経歴を持つ。 私は最近、フォーミュラワンのレーシンググループのテクノロジーセンターに座り、ドライバーが高強度のトレーニングセッションに取り組む様子を見ていた。彼はシミュレーターを使って自分の「ゴースト」と競走していた。ゴーストとは、前回のセッションでの最速ラップをデジタルで透明に記録したものだ。前回のベストタイムにおけるブレーキングポイント、エイペックス、スロットル入力のすべてが、彼のトラックビューに重ねて表示されていた。その瞬間、ドライバーはグリッド上の他のドライバーと競走しているのではなく、過去の自分自身と競走していたのである。...
Racing Against Your Own Ghost: A Path For Improving Performance
Brendan P. Keegan is Chairman & CEO of bFEARLESS Ventures and is a 6-time CEO, 23-time board director and 3-time best-selling author. I was recently sitting in the technology center of a Formula One racing group, watching a driver engage in a high-intensity training session. He was using a simulator to race against his "ghost"—a digital, transparent recording of his fastest lap from the previous session.
The Source Filter: Engineering Credibility in an Age of High-Volume Criticism
See More - stock.adobe.com In the early stages of my career, I operated under a significant strategic flaw: I allowed everyone’s opinion to carry equal weight. I treated the feedback from an experienced mentor who had scaled global organizations with the same consideration as the armchair critic who had never put themselves on the line.
Why an Athlete's Retirement Made Me Rethink My Exit After Building a $2.7B Company
Great leaders should step down at their peak — not after decline — using Barry Sanders' retirement as a model for preserving legacy and enabling strong succession. Barry Sanders walked away from the NFL 1,457 yards short of the all-time rushing record. He had rushed for 1,491 yards the season before and likely had another four or five seasons left in him. He retired anyway. To anyone who confuses longevity with achievement, the decision looked irrational.
Re-engineer the path to high performance
The core mindset that differentiates champions from average performers is rarely discussed as a matter of engineering. Most leaders operate under a cloud of perpetual frustration, a state often brought on by the toxic self-reliance that rejects the need for support, or a cynicism that assumes collective disappointment. However, the reality of a fearless leader is found in something entirely different: a strategic allocation of where expectations are placed.
Forbes JAPAN 公式サイト（フォーブス ジャパン）
ブレンダン・P・キーガン氏はbFEARLESS Venturesの会長兼CEOであり、6度のCEO経験、23社の取締役、3冊のベストセラー著者である。 誰もあなたにはなれない。それこそがあなたの力だ。競争に取り憑かれた世界において、これは最も活用されていない戦略である。 ほとんどの人は、キャリアを通じて競合他社のわずかに優れたバージョンになろうとする。わずかに速く。少しだけ賢く。もう少し洗練されて。他者のやり方を研究し、それをわずかに上手くやろうとする。市場をベンチマークし、平均をわずかに上回ることを目指す。 それは底辺への競争だ。なぜなら、平均的であることにおいて、あなたを上回る実行力を持つ人は常に存在するからだ。同じゲームでより懸命に働く競合他社は常に存在する。あなたと同じことをしようとする何かにおいて、あなたを打ち負かす人は常に存在する。 では、代替案は何か。競争をやめて、差別化を始めることだ。 ユニークネス・スタック あなたとまったく同じ経験、視点、能力の組み合わせを持つ人は誰もいない。誰も、だ。...
Engineering Reality: Why the Creation Cycle Informs High-Performance Leadership
BullRun - stock.adobe.com “What you think, you become. What you feel, you attract. What you imagine, you create.” Most people dismiss these three statements as “woo-woo” mysticism—the kind of metaphysical fluff that promises success through magic. I see it differently. I graduated from Rensselaer Polytechnic Institute, and when you are trained as an engineer, you learn that every outcome is the result of a system. Your mind is no exception.
Your Unfair Advantage Personally
Brendan P. Keegan is Chairman & CEO of bFEARLESS Ventures and is a 6-time CEO, 23-time board director and 3-time best-selling author. No one is you, and that is your power. In a world obsessed with competition, this is the most underutilized strategy. Most people spend their careers trying to be slightly better versions of their competitors. Marginally faster. Incrementally smarter. A little more polished. They study what others do and try to do it slightly better.
The quiet strength
A warrior’s strength is quiet, built in silence, revealed in storms. The loudest person in the room is rarely the strongest. I’ve spent decades in boardrooms, and I’ve learned to spot the difference. The executives who feel the need to dominate every conversation, to prove their intelligence at every turn, to make sure everyone knows how important they are—they’re usually the most insecure. They’re performing strength because they don’t possess it. Real strength doesn’t announce itself.
The Humble Confidence
peopleimages.com - stock.adobe.com “Humble enough to know I can lose it all. Confident enough to know I can get it all back.” This is the psychological sweet spot that defines elite performers. Too humble and you never take the shots that create breakthrough success. You defer to others. You second-guess yourself. You wait for permission that never comes. You play small because you don’t believe you deserve big. Too confident and you get blindsided by risks you couldn’t see coming. You ignore warnings.
Your inner circle shapes your success
“You gotta hang around winners so your wins don’t sound like you’re bragging.” This might be the truest thing anyone’s ever said to me about success. For years, I downplayed my wins due to an intimidating environment. In rooms where ambition was suspicious and achievement was threatening, I learned to stay small. To qualify every success with self-deprecation. To apologize for wanting more before anyone could accuse me of thinking too highly of myself.
The Five-Year Overnight
“Overnight success takes at least five years of work.” The headlines. The celebration. The “liquidity event” that gets written up in business journals and mentioned in introductions. That’s the story people want to hear. Nobody wants to talk about the years of grinding that made it possible. The 4:30 AM whiteboard sessions alone in the gym. The failed initiatives that consumed months before we killed them. The pivot points that felt like existential crises.
Incorporate AI into your daily life to be more productive
I never thought I’d become an AI evangelist. I’m a sports enthusiast, a car guy, and someone who’s spent 30 years in industries where success comes from building relationships, reading rooms, and trusting your gut. About five years ago, I started using AI in my business life, but not in my personal life. AI in my personal life was more of a curiosity. Today, I don’t know how I functioned without it.
The Cost of Inaction
If you don’t go after what you want, you will never have it. If you don’t ask, the answer will always be no. If you don’t step forward, you’ll stay in the same place. Three sentences. Three unavoidable truths. And most people spend their entire lives pretending they aren’t real. I’ve sat across from hundreds of talented people who had every reason to succeed and one invisible force holding them back: the belief that not trying protects them from failure. It doesn’t. It guarantees it.
Leading through crisis in the boardroom
I had been an outside board director for a company for nearly two years. I knew the CEO and CFO well and was often around the leadership team. But the first time a real crisis hit, we quickly learned more about the CEO and their team. In fact, it only took 48 hours to really see what leadership the company had. It was 2008. Markets were collapsing. The company had 72 hours before violating a debt covenant that would trigger default and potential bankruptcy. The CEO was frozen.
Pit Stop Leadership: What Endurance Racing and F1 Teaches Us About High-Performance Teams
I’m standing in the United Autosports & McLaren garage in Mt. Fuji at the 6 Hours of Fuji race watching the pit crew prepare. Twelve mechanics, each with a specific role, rehearsing the choreography they’ve practiced ten thousand times. The car will be stationary for 5.5 seconds. In that time, they’ll change four tires, inject fuel, make adjustments and send the driver back onto the track at 200 mph.
Transform your business with these 5 AI cheat codes
Brendan P. Keegan|Published 59 minutes ago Last week, I was at a board meeting where the CEO proudly announced they’d formed an “AITask Force.” Six months in, their grand achievement was a chatbot that could schedule meetings. Meanwhile, their competitor had already automated 40% of its customer service and was using AI to predict churn three months in advance. Guess which company’s stock I’d rather own? AI in business is like having a turbocharged engine in your race car.
5 trucos de IA para arrasar a tu competencia en los negocios
La semana pasada, estuve en una junta directiva donde el CEO anunció con orgullo que habían formado un “grupo de trabajo de IA“. Seis meses después, su gran logro era un chatbot que podía programar reuniones. Mientras tanto, su competidor ya había automatizado 40% de su servicio al cliente y estaba usando IA para predecir la deserción de clientes con tres meses de anticipación. ¿Adivina las acciones de qué empresa preferiría tener?
5 AI cheat codes to leave your competition in the dust
Last week, I was at a board meeting where the CEO proudly announced they’d formed an “AI Task Force.” Six months in, their grand achievement was a chatbot that could schedule meetings. Meanwhile, their competitor had already automated 40% of its customer service and was using AI to predict churn three months in advance. Guess which company’s stock I’d rather own? AI in business is like having a turbocharged engine in your race car.
The Coachability Gap: Why Your Career Depends on Learning How Your Leader Actually Leads
I once had a rising star on my team named Alex who had everything going for him — brilliant mind, strong work ethic, clear ambition. He also had one fatal flaw: He wanted to be coached on his terms, not mine.
The pressure privilege
Recently, I watched a dozen 21-year-olds stress about their career prospects, job interviews, and prospect pipelines, jockeying on how challenging this was to manage. The irony wasn’t lost on me—they were slightly upset about the workload in front of them and the pressure they felt, while also talking positively about what a great position they were in. That’s when it hit me: They had figured out something most later career professionals forget as they go about their careers.
The Great Busyness Delusion: Confusing Motion with Movement
Last week, I asked a good friend what they had accomplished that day. She launched into a fifteen-minute monologue about attending three meetings, responding to forty-seven emails, updating five spreadsheets and reviewing countless documents. When she finished, I asked her again: “But what did you accomplish?” The silence that followed was deafening. She’d confused being busy with being productive, motion with movement, activity with achievement. She’s not alone.
Geração X, o tempo está correndo: você tem 10 anos para garantir sua aposentadoria
Se você é da Geração X e está chegando aos 50 anos, aqui está a verdade incômoda: você tem cerca de 10 anos para fazer as pazes com a aposentadoria. Não "quase certo" ou "quase certo". Na verdade, certo. Porque, ao contrário dos baby boomers que tropeçaram na maior expansão econômica da história, você não recebe uma segunda chance. Veja a história desses dois vizinhos. Ambos completaram 65 anos no mesmo ano.
The Inconvenient Truth About Warriors: Why We Only Love Them When We Need Them
Recently, I posted a quote on Instagram and LinkedIn that said, “No one loves the warrior until the enemy is at the gate,” and the messages flooded across my network — from compliance officers to sales rainmakers to cybersecurity specialists. And the message was clear — from scary person to savior when the “event” happened. This was a theme, but also sincere commentary about how difficult it is to be the warrior.
A Generation X guide to retirement planning
If you’re a Generation Xer staring down the barrel of your fifties, here’s the uncomfortable truth: You have roughly 10 years to get this retirement thing right. Not “mostly right” or “close enough.” Actually right. Because, unlike the boomers stumbling into the greatest economic expansion in history, you don’t get a mulligan. Let me tell you a story about two neighbors. Both turned 65 in the same year.
The Fearless Professional's Guide to Getting It Right
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The four-year exit plan: what I wish I'd known before selling my business
Selling your business is a long-term proposition, not a short-term reaction. I remember selling the first business I was CEO of.
4 Emotional Intelligence Mistakes We All Make (And the Words That Betray Us)
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4 Ways boards of directors can leverage AI for better meetings
Last month, I watched a board chair spend 20 minutes hunting through a 200-page packet for a single financial metric mentioned in passing three meetings ago. The CEO quietly sat there, tapping his pen; the other directors checked their phones. Meanwhile, the clock ticked by what should have been a strategic discussion about market expansion. If you’ve ever sat in a boardroom, you know this scene. Board meetings often devolve into information archaeology instead of strategic governance.
Building and Breaking Company Culture: The Hard Truth About What Really Matters
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Eight common-sense tips (that aren’t as common as you'd think) for managing your board of directors
Leading a board of directors is one of the most critical yet challenging responsibilities for executives and entrepreneurs. Whether you’re a startup founder navigating your first institutional board or a seasoned CEO managing a complex structure, board leadership can make or break your company’s trajectory. The best Chairs and CEOs understand that a well-managed board isn’t just a governance requirement, but an asset that can unlock growth and open doors to new opportunities.
How a Company's Culture Impacts New College Graduates Entering the Workforce
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4 Ways To Link Your Transformational Strategy to Culture Through Story Telling
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10 Practical Lessons for Building a Transformation Leadership Team
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Shifting Gears: The Impact of Women Driving Change in Motorsports
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Racing’s Role in Shaping Modern Masculinity: Redefining Strength and Vulnerability
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