• Linchpin: Business Partnerships That Work

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  • The Blog

    Cool & useful stuff I'm reading or listening to this week

    Best podcast this week - Elon Musk gives Kevin Rose an example of reasoning from 1st principles....
    Jeff Bezos may be the best CEO working today. He's also a lucid and incredibly helpful writer on...
    An article on leadership, a POV piece on corporate culture and a look into the near-future of A.I...
    Two great articles this week that highlight two *very* different companies: First, the WSJ had...
    E.M. Forester wrote a story in 1909 that should be a must-read for people who are interested in...
    The best thing I read or listened to this week was this terrific, deep dive into Google's quest...
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  • Longer Posts

    LinkedIn posts on management, strategy, deals & negotiations

    December 21, 2016

    “She’s impossible,” my friend, Edgar said, shaking his head, morosely. “Whatever I do, it’s wrong. Whatever I try, it’s—” he paused, searching for the right word, “insufficient.” He heaved an enormous sigh. We were sitting at a long marble-topped bar, and Edgar — an extremely talented peer of mine — was talking about his boss, not his girlfriend.

    November 29, 2016

    When Francis Ford Coppola got offered the job to direct The Godfather, he was not yet Francis Ford Coppola. He was 31 years old, in debt up to his eyeballs, and he was only offered the job after seven other directors had turned it down.

    November 15, 2016

    Recently, as I sat nursing a glass of red wine at the end of a long day, I had an epiphany. I was feeling troubled and kind of irritable. Why? As far as I knew, there were no calamities or looming storm clouds. So what was bothering me? After a minute it hit me: while nothing had really gone wrong during the day, nothing had really gone right, either.

    August 30, 2016

    Sitting in my elegant, corner office, I felt like a fraud. I had been running a business (my first) for the better part of a year, and I was finally getting around to admitting to myself that I really had no idea how to fix it...

    July 6, 2016

    You're wrong. You’ve been wrong before, and you are, in fact, wrong at this very moment, wrong about a number of things. Some of these errors are small, and others are large. It’s very possible that one or more could cripple your business or damage your career. This is true about you, and it is true about me...

    May 31, 2016

    Bad bosses: we’ve all met them. In fact, you may believe you have one. If so, you are not alone. A recent poll by Monster.com found that 30% of employees think their boss is horrible. A mere 15% rate the boss as excellent...

    April 27, 2016

    In the spring of 1990, I found myself in Boston, bleary-eyed and culturally dazed from a stint teaching English in Japan. I was looking for a job, and I had few practical skills, fewer contacts and no real idea of how to get started...

    April 12, 2016

    Imagine, please, a moment of awkward silence with a quasi-stranger. You’ve had them. We’ve all had them. Picture one.

    Got it?

    OK. The genesis of this post was one such moment...

    March 22, 2016

    “It was awful,” my father said, cracking open a beer. We were sitting on the porch on a gentle summer evening, and he was recalling an event from several decades earlier that had been one of the worst experiences of his professional life. “Terrible,” he added with a shudder.

    So what was this task that my father remembered as terrible and awful all these years later? What had given this strong and even-keeled man pause?

    March 22, 2016

    It was cool in the room, but I was sweating when I put down the phone. I had just received the shellacking of my life from my boss. As I sat there, trying to collect myself, one thought kept recurring: I’d been sandbagged, and I hadn’t even seen it coming...

    January 4, 2016

    Forbes says only 8% of people achieve their New Year's resolutions. 8%! (The postcard above is from 1909, suggesting this is not a new development.) In this, then, the season of failed resolutions, I thought I'd lay out an alternative approach. Forget resolutions this year. Narrow your focus. Just try to win the day...

    November 30, 2015

    “Okay, I’m going to explain this to Chris. I figure if he gets it, everybody gets it.”

    I was sitting in the back of a crowded conference room, filled with about forty people, when the speaker, our boss, uttered this memorable sentence, and, yes, I was the Chris to whom he referred...

    November 10, 2015

    My last post covered the best career advice I ever got. It came from a highly accomplished executive, a number of years my senior, and you can read about it here. The second best piece of career advice I ever got came from a college dropout I met on a summer job when I was 19 years old. Well, technically, he may not have dropped out at that point, but I don't think he finished...

    November 2, 2015

    “I have no idea how I would even start to get from where I am to where you are,” I said morosely. I was talking to my boss, and I meant it metaphorically.

    I was a newly minted MBA, working in management consulting, and I hated my job. Now, I know lots of people who enjoy consulting. You get to learn a lot about a variety of industries, you work with smart people – yeah, yeah. All true. I still hated it...

    October 15, 2015

    “This sucks. We should walk,” I said.

    It was a tense moment. I had been negotiating a deal, a partnership, for a couple of weeks. If it worked, it would be lucrative for both of our companies. The lead guy on the other side, I’ll call him Arnaud, and I had gone back and forth a number of times and I thought we were pretty close to agreement on the economic terms. My latest offer had been just a hair below what he wanted. Today, he’d come back to me with a curve ball...

    September 29, 2015

    Dave, our VP of marketing, loped into my office. “It just came over the wires,” he said. “They declared bankruptcy.”

    “OK, time to place the call,” I said.

    We’d been waiting for this for a while. The company Dave was talking about was a rollup that had gobbled up a wide variety of travel companies in the U.S. and Canada over the preceding several years. Rollups sound like a good idea: raise some money, consolidate a fragmented industry and realize the benefits of running a scale operation...

    September 8, 2015

    It was the biggest break in my career to that point, and I was pretty sure I was blowing it.

    Let me back up. It was 3:00 A.M. in Stockholm, and I was wearing out the carpet in my tiny hotel room as I paced the floor. There had been a shakeup in my company, and I had been offered a big promotion: from EVP to President of the division I’d been managing as well as responsibility for a new group that did negotiations, purchasing and logistics for a large tour operator. There was just one catch: I had to move to Europe and persuade a group of Swedes to move from Stockholm down to Amsterdam. The plan was to merge them with a team that was already based there. Amsterdam is great, I thought. How hard could this be?

    September 17, 2015

    I listen to podcasts all the time: when I’m exercising or commuting, raking leaves or sitting in an airport, you name it. It's a great way to make slack time productive (and fun). I’ve become a little bit obsessed (My wife argues that last should read "a LOT obsessed.") and I am always fine-tuning my mix. After I ran through some of the popular ones on iTunes, I went looking for podcasts on business.

    August 11, 2015

    “A two-by-two matrix?” the Chief Marketing Officer asked me. “That’s kind of 1975, isn’t it?”

    I was working with a client executive team on product rationalization. We were developing a suite of new products and – in this world of constantly narrowing consumer attention – when something new comes in, something old has to go out. I’d presented a two-by-two matrix that contrasted growth and profitability to help evaluate their current offerings, and this skeptical response was not exactly what I wanted to hear.

    Lessons on Customer Loyalty... From Bono

    July 21, 2015

    My wife got us tickets to U2 for my birthday this year. Bono and Co. put on a great show, as expected. Beyond that, though, I came away marveling at the ways in which the band managed to connect with fans and make the experience memorable. I imagine them asking each other: “How can we make an arena show as memorable and intimate as a club gig?” There are customer loyalty lessons here that can apply to many different types of business — whether or not your career requires the wearing of leather pants.

    July 7, 2015

    I remember my negotiations class in business school. We dutifully took notes on things like how to determine your “BATNA,” or the risks of letting the other side “anchor” you to a price -- all that stuff. While there were some useful tips, it felt kind of like learning how to dance by studying physics.

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  • The Work

    Linchpin creates partnerships that work, between companies and within them.

    Partnering for growth

    Need to reach new customers?

    Get access to new customers through partnerships. Linchpin stays involved beyond the actual deal to help you optimize the program.

    Partnering for monetization

    Need to extract more value from your existing customers?

    Monetize your existing customers by partnering with companies that offer complementary products/services. Linchpin works with you to find the right partners and to ensure product/market fit.

    Executive Coaching & Mentoring

    Need a sounding board for strategic and managerial issues?

    Get access to an independent "sparring partner" to help you or someone on your team develop solutions to tricky strategic, managerial or staffing issues. Linchpin builds the deep relationships that enable effective coaching.

    Advisory services

    Need specific strategic or managerial advice?

    Linchpin also does short term advisory projects. Areas of expertise include market/product strategy, product positioning and managerial efficiency.

  • About Chris

    Practical, effective solutions to complex problems

    Chris O'Brien


    Chris O’Brien has spent nearly 20 years developing and implementing partnerships in a variety of industries including credit cards and other financial products, travel and education. During this time, he has worked with professional sports teams, universities, large membership organizations, financial services firms, airlines and a variety of other organizations.

    Prior to founding Linchpin, Chris spent 9 years at the Kessler Group, the affinity marketing pioneer. For the final six years, he served as Chief Operating Officer. Before that, he was President, Travel and Affinity for Smithsonian Business Ventures, the business arm of the Smithsonian Institution. Prior to that, he was at EF Education where he managed several businesses in the U.S., Latin America and Europe.

    Chris holds an MBA from the Amos Tuck School at Dartmouth College, a BA from Middlebury College. He is a Senior Advisor to the Kessler Group and serves as Vice Chairman of the board of the Trinity Boston Foundation.

  • Testimonials

    Practical, effective solutions to complex problems

    Gary Phoebus CEO, NEA Member Benefits

    "Think Henry Kissinger with a fat Rolodex. Chris knows everyone and those relationships were built on trust and an ability to bring parties together quietly, effectively and drama free."


    Jon Sandler CEO, Decision Resources Group

    "In the simplest terms, Chris gets things done. By using his deep domain knowledge, his remarkable interpersonal skills, his patience and his smarts, Chris is able to get folks to “yes.” Better still, he does it in a way that leaves all sides smiling and willing to engage with him on an ongoing basis."

    Joe DePaulo CEO, CollegeAve Student Loans

    “I’ve had the pleasure of knowing Chris for more than 15 years, and he brings integrity and honesty to everything he does. As a result, he has the rare ability to navigate complex deals with demanding clients and emerge with all parties feeling good after the deal is done. He is first class!”

    Shikhar Ghosh Senior Lecturer, Mel Tukman Faculty Fellow, Harvard Business School

    "Whether it is sourcing a new opportunity, negotiating a deal, facilitating a negotiation or solving a messy organization crisis, Chris keeps people and deals together. Perhaps this is because he is particularly good at facilitating a dialogue and getting even the stickiest problems 'unstuck.'"

    Louise Julian Former Chairman & CEO, EF Education

    "I have relied on Chris to parachute into a wide variety of complex situations all over the world - and resolve them."

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