If you’re a technology leader, you know there’s no shortage these days of innovation events and programs available to you. CXOs attend events for a number of reasons, whether for career advancement, peer networking, or simply to learn about emerging trends in the industry. Unfortunately, there are few truly great options out there that provide a high value return on investment, and are actually worth your time.

“CIOs must be vigilant with their time,” says Gary Beach, publisher emeritus for CIO Magazine. “Smart technology leaders continually assess the value one derived from various time and resource investments, and how that value may play a role in successful execution of transformation efforts.”

Personally, I see four main constituencies playing a role around corporate technology leaders and the innovation events they can attend: technology OEMs, channel partners (e.g. value-added resellers (VARs), managed solution providers (MSPs), integrators, and consultants), venture capital firms, and for-profit, sponsor-based CXO event production companies. Let’s take a closer look, ask the tough questions, and provide some answers which let you make more informed decisions about how to spend your time, money, and resources.

Technology OEMs

Manufacturers of tech products are limited in the insights into industry trends and transformation they can provide because, at the end of the day, they are beholden to the products and services they sell. Selling these products is what drives the decision-making around hosting CXOs for any type of social networking event, EBC, or other program. To be clear: this bias towards their own products isn’t a bad thing – but it’s something a CIO should keep in mind when determining where to spend their time.

Ask yourself a few questions before going to an innovation event hosted by an OEM: What do they want from me? What do they hope to gain from my attendance? What insight can they offer me? By asking these questions, you can set your own expectations properly. There is definitely value in these events, but does it match the time and effort you put into it? The main benefit of these events is typically road-mapping future tech, maintaining confidence in your past investments, or losing that confidence and being able to make more-informed decisions regarding introducing a competitor’s solutions.

VARs, MSPs, SIs and Consulting firms

Channel partners have a broad view of the industry, operating between OEMs and their customers. This puts them in a unique position to provide insight specifically for their customers’ needs. However, for every channel company providing significant value in their events, you will find there are a hundred who will make you wish you had that time back in your life. These companies have a wide spectrum of events: training programs, innovation days, tech summits, annual conferences and dinners. But it’s exactly that extensive range that makes it difficult to find the needle in the haystack.

When considering the time and money you’ll spend here, CIOs must ask themselves: What can I expect to gain from attending?  Who is developing the content and to what end? Is my voice included in the agenda? What motivates the organizers and how will that affect the experience I will receive?  Generally speaking, you may find that many events in this category are a poor investment of a CXO’s time. Instead, they are more valuable for mid and entry-level IT leaders.

Venture Capital Firms

Not all VCs are created equal. Some deliver significantly more value than their average peers.  There are typically two types of VC events CXOs can participate in: portfolio days and tech summits. The former is essentially a VC-hosted speed-dating event, in which corporate clients are pitched on the products and services of the companies the VC has invested in. The latter is a larger-scale annual version of a portfolio day, hosted at a nice venue with nice amenities and a big-brand speaker or two. Dozens of CXOs from various organizations attend, so there is some value in peer networking. The challenge is that the content and thought-leadership is chosen for you, not by you, with few exceptions (There are 2, maybe 3 firms in the valley who go above and beyond in providing value through their tech summits).

CXOs would be wise here to ponder the tremendous value they bring to these interactions, because it may be greater here than in any of the other examples. The questions to ask here are: How valuable is my input and feedback? How does my knowledge-transfer allow them to be more successful, and what is that worth?  Is this a fair exchange of value?

On average, the CXO in this scenario has become the product. The value is lopsided in favor of the VCs and startups because the CXOs bring so much more value to the table. In  particular, they offer product/market fit feedback and insightful data that can inform investment decisions. There are a select few VCs who are genuinely interested in helping CXOs, putting their needs first, and who want to have a mutually beneficial exchange. However these VCs understand that, being one firm with one portfolio of companies to choose from, they are limited in the solutions they can bring to the table to advance a business initiative.

For example, the folks at Menlo Ventures take a longer term approach to their CXO relationships and understand how to curate and run first-class events that provide meaningful value for all. “We first seek to understand the business needs and priorities of CXOs, then work to deliver relevant content, thought-leadership, and companies to present, even if outside the Menlo Ventures portfolio. The relationship only works if the CXO’s would look forward to doing it again ” says Matt Murphy, General Partner, Menlo Ventures

For-profit, sponsor-based event production companies

We’ve all been there. For a CIO, these events are typically free or nearly free, but they do take up a good chunk of your time.  They’re held at a high-end venue with great food, drinks, and an agenda designed for maximum marketing impact for prominent VCs, a select few emerging tech startups, and high-profile CXOs.  On the surface, it seems like a good idea. But when you pull back the curtain on the operational model of these event production companies, the story looks entirely different. All the answers you need are in response to three simple questions:  Who pays?  How is the agenda created?  Who will benefit from attending?

In a recent conversation with Ralph Loura, former CTO of Rodan + Fields, it became quite clear how the industry is shifting: “There is solid value in the peer networking aspect of sponsor-based events, but nothing you can’t get from some other CxO networking groups as well. Beyond that, CxOs who really want to maximize the value return for their time are increasingly prioritizing closed groups or consulting arrangements that typically involve an annual a membership, fee or subscription, or engagement fee. The non-sponsored nature of these groups mean they can be designed and built around the needs of the CxO members allowing for a greater focus on return on invested time of the participants.”

The model is simple: reach a point in the business where you can reliably confirm a certain number of CXO attendees, and sell that attendee list to sponsors for access. Those sponsors typically come in the form of tech companies wanting to sell their products to CIOs, and VCs wanting to grow the companies they’ve invested in. While many CXOs are becoming more aware of the operational model of these events, causing a slow but steady decline in attendance numbers in past years, many still show up only for the peer networking. If you’re not the big brand CIO who is being paid directly to attend, speak, and draw attendees, this kind of event may not be right for you.

Final Analysis and Recommendation

This is one of the best times ever to be a CIO. However, if you accept the premise that demands on a CIO’s time are greater now than ever, you must also believe that a CIO’s ability to succeed in today’s rapidly evolving business climate depends on making wise choices regarding where to spend their time.

  • Tech OEM events are necessary if the relationship is strategic to your business and the event can be customized to your needs.  However, you shouldn’t invest in these more than once every couple of years.
  • While channel partners are often viewed by many CIOs as wolves in sheep’s clothing, there are a select few that can add value to your senior and mid-level leaders. Delegate participation to them if you are confident the partners you’ve chosen are putting your needs first.
  • Maintain relationships with 2 or 3 VCs who are committed to helping you advance your business initiatives, and don’t let the value exchange become one-sided. Tap into the thought leadership you need, get portfolio updates every couple of years, and remember the innovation exposure you’ll get from any single firm is extremely limited.
  • Finally, attend sponsor-based events if you have nowhere else to turn for peer networking.

Time is money.  Before investing any of your precious time to attend a future event, ask this question: “If I attend, will I be the customer or the product?”  The best way to achieve maximum value in exchange for minimal time and effort is by connecting to offerings which are purpose-built to serve you.  The answers to the magic questions there should be easy: I am paying for this. The people helping me are focused on creating value for me, and me only. Nobody can pay for access to me. I am still the customer.

If you have questions or are interested in more specific recommendations I can be reached at

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14,505 Feet of Misery That I’m Grateful For

With a summit elevation of 14,505 feet, Mt. Whitney is the tallest mountain in the contiguous United States. Because of its location in the Sierra mountain range in California, it is a popular climb for mountain climbers with a wide range of skill and experience. I’d never been drawn to mountain climbing — certainly not to this degree — but I was curious as to what climbers saw in such an accomplishment. I thought the best way to understand was to try it myself, and maybe I would even discover a new attraction of my own.

I can now safely say that I have no interest in mountain climbing. But I am grateful for the lessons I learned along the way, even if they came through trial and error.


Climbing a mountain seems fairly simple in abstract, right? Not easy, but simple. You get the right equipment and start climbing until you reach the top. But there are countless wrong choices you could make that might have little consequence at Sea level, but could cost you dearly on your ascent. Packing too heavily, underestimating altitude sickness, hiking in snow vs. dirt trail, not properly calculating caloric intake and output…these are all little things that novice mountain climbers take for granted, and often they come to regret it.

I took some of these things for granted myself and made assumptions that only made the trek up Mt. Whitney that much harder for me. Business can be much the same. There are any number of little details that may not seem important before you begin but that you’ll find can have a huge impact on your success. The solution? Do your homework. It’s important to research every aspect of the venture you’re about to begin — whether it’s scaling a mountain or starting a business — so you know what to expect from others have taken the same path before.

Planning and analysis will typically lead you to a more pleasurable experience, and a more successful outcome. Keep in mind, though, that you don’t want to overdo it, as overplanning tends to cause paralysis.


There was a moment about one mile from the summit, less than an hour to go, when I felt my body shutting down. I was nauseous with a splitting headache, and I couldn’t seem to take in enough oxygen for proper muscle recovery. Quitting would have been so easy, but I somehow managed to press on to the top. My mind pushed my body further than I had thought possible.

The “body” of your business may suffer threats from competitors, discouragement from naysayers, abandonment from employees or customers, or financial straits. If you’re in a negative mindset, these challenges might prompt you to quit. But with a committed and unwavering mind in their pursuit of the mission, they are speed bumps at most.


In Man’s Search for Meaning, Victor Frankl talks about the fundamental human drive being to find life’s “potential meaning under any conditions.” “Life is never made unbearable by circumstances,” says Frankl, “but only by lack of meaning and purpose.” He goes on to discuss the belief that one’s spirit can rise above his surroundings: “When we are no longer able to change a situation, we are challenged to change ourselves.”

If you’ve read this wonderful book, you know the suffering described within is unimaginably worlds apart from my experience so there is truly no comparison. But they both offer valuable lessons about what can be gained in the process. Suffering can teach us who we are, and sometimes that knowledge can be one of our greatest resources.


My attempt at mountain climbing was an unforgettable experience with three great friends for which I’ll always be grateful, and there were plenty of people on the mountain having a much better time than me! Even though I felt no enlightening revelation on the summit and it didn’t spark a new hobby, I learned a little more about who I am as a person, and there’s great satisfaction in that.

I was reminded of two things in my professional life as I reflected on this experience. First, if you don’t go for it, you’ll never know…and you may come to regret not knowing and not having tried. And second, it is healthy to be honest with yourself and shed, whether it’s a hobby that isn’t for you, a line of business or a product that didn’t go as well as you hoped.

I would still highly recommend this adventure to anyone even mildly interested. Just don’t skimp on the research and planning!


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How Much Can Your Business Handle

A friend of mine recently asked a small group of business leaders an interesting question: “In how many organizational areas do you need to truly be excellent? Where, based on complexity and bandwidth, do most organizations tap out?”

We’d all like to say that we never tap out, that we have endless bandwidth and energy, or at least that we know exactly where our limits are. However, the answer is most often a less satisfying, “It depends.” There are a number of variables that influence how much you, your team or your business can actually handle. It’s these variables that make this question truly fascinating. I’d argue that it’s actually less about the volume or about how much you can handle. It’s really about what a company needs to truly excel in more than one area.

I instantly thought of two things: organizational health and strong, effective leadership. These two things have to go hand-in-hand in order to have maximum overall success in an organization.

Strong Leadership

Firstly, you need strong, cohesive leadership in place in order to achieve excellence in any organizational area, let alone multiple. This starts with leaders chosen based on their expertise and experience. The organization’s success depends on the leadership team’s ability to lead and manage no matter what the challenge or tedium of the business. With a solid leadership team foundation the communication and messaging can stay consistent and focused throughout, enabling the enterprise to simultaneously focus on multiple areas of the business.

Organizational Health

Assuming you have effective leadership in place, your bandwidth to excel in multiple areas becomes dependent on the organizational health of the company itself. The “health” of the organization can be measured in categories like: clarity of purpose, effectiveness of communication, trust, alignment, and engagement. With all of these in place, I believe that there truly is no limit to what a company can accomplish. Foundational, organizational health allows for repeatable expansion and scale. Without organizational health, trying to excel at even just one or two objectives will be a challenge.

At the end of the day a business at its core is made up of people. As a result, often the capabilities of the business depend on those same people. In a healthy organization with a strong leader, everyone’s respective strengths will be amplified, so that the company can take on any number of organizational ventures and excel. Without strong leadership AND organizational health, you will find that the ability for your company to take on new challenges successfully is almost impossible.

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The Death of Enterprise IT As We Know It

IT as we once knew it is dead. In fact, some Silicon Valley CIOs, such as Wendy M. Pfeiffer at Nutanix, have even gone so far as to ask, “Why should IT continue to exist?” Of course, enterprises will always need technology, but the way that technology is used is quickly changing. Modern enterprise IT must take on a more consumer-focused culture and business model to remain relevant in the future.

At The Syndicate Group, we’ve had a front row seat to see this evolution and how it’s affected the top enterprises in the world. Thanks to our Innovation Experience Program, we see that some businesses, like Nutanix, have embraced  and are leading the charge, while others have hesitated.

Why Consumerization?

Today, technology is so pervasive and woven into the fabric of our everyday life,  that it’s actually a challenge to go without it. Today, your smartphone is millions of times more powerful than all of NASA’s combined computing in 1969, the year we landed on the moon. Consumers of all ages, but especially younger generations, keep up with their contacts — and even find new connections — all over the world through social media. No longer willing to pay the hefty price of word processing software, consumers can use free apps to write and share documents with ease. They can keep up with their favorite businesses through the use of apps.

But when these same people clock into work, too often do they find enterprise IT apps and software that are fine, but don’t live up to their consumerized expectations on how technology should work for them. They might not function as quickly or be as versatile as the consumer IT products that employees are used to at home. Sometimes it’s as simple as a less attractive interface. This might seem shallow, but studies have proven again and again that consumers are attracted to aesthetically pleasing apps and software. Overall, enterprise IT has evolved to be less…people-friendly than consumer technology. And at the end of the day, businesses are made up of people. People that want to be enabled as efficiently and effortlessly as they are on their personal time. In order to successfully address the technology needs of employees, technology leaders need to think of their corporation not just as an enterprise but a community of consumers.

From my vantage point, I have found three main areas of focus to successfully bring about a consumer focus to the IT in your enterprise; the people, the process, and the technology.

The People

For this evolution of IT to thrive, it’s clear that leadership and culture will be critical. IT teams need to be more directly involved in various business units, so that their success can be more directly aligned to the success and satisfaction of the business they serve. As always, it starts with leadership and then this change can filter down through the ranks.

I’ll save the in-depth analysis of this aspect of transformation for another time. For now, defer to organizational health professionals like The Table Group and their thought-leadership expertise.

The Process

A major priority of IT groups now should be creating supportive structures that can sustain both people and technology through this shift. Tim Guleri, Managing Director at Sierra Ventures, suggests that AI competencies and a strong intelligence layer may be the key to a successful transformation. “IT needs to implement better tools for data collection and analytics,” he says, “so they can be more intimately aware of user adoption and usage, thereby enabling faster and easier processes and early identification of trends that will need to be supported at scale.”

Experimentation frameworks are also crucial to the consumerization of IT. As with any major change, there will be a period of trial and error. Organizations should have repeatable models and support for low-friction trials in order to reach the end goal of efficient adoption and usage. Efficiency is after all, the great appeal of consumer IT, but traditional IT has only recently been confronted with these consumer expectations.

The Technology

Last but not least, what kind of technology is going to be used in this IT transformation? Many corporate IT groups are looking at three main categories:

  1. Bridge Technologies– (i.e. Dropbox) technology originally designed for consumer markets that can  be adapted and applied to enterprises
  2. Consumerprise Technology– (i.e. Slack) technology built specifically for enterprises but created with a consumer mindset
  3. Homegrown tech

To accomplish this transformation, it is essential for IT leaders to first focus on the people and process aspects first, as those steps will allow the appropriate technologies to come into the mix. As IT organizations continue to evolve and be facilitators and accelerators of relevant technology adoption, I believe the entrepreneur and venture communities will adjust accordingly.

Consumerization of enterprise IT is just one focus area you can address  through our Innovation Experience program. In the coming series, we’ll discuss other challenges that we work to tackle through our Innovation Experience program.

Would love to hear what the biggest priorities are for your organizations, email me at

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I always wanted to try rally racing. It didn’t always seem like an opportunity I would have, but when I was offered the chance, I jumped at it. I had a lot to learn through training, and the race itself was a thrill of risks and challenges. The whole process taught me a number of lessons about myself as well as about business. But through it all, the sensation I consistently felt was fun. It was everything I hoped it would be and more. I was truly enjoying myself.

And that, as it turns out, was the the fourth – and maybe most important –  lesson I learned about business by rally racing. In the daily routine, we can forget that business is an adventure. Every entrepreneur or innovator who ventured to start a business took a big risk, a leap of faith. They decided to follow a path they felt strongly about. And that adventure can be thrilling, but it can also be terrifying.

If rally race car drivers become so fixated on winning — or on not crashing — it hardly matters whether they win or not, because they won’t be able to enjoy the experience. That’s not to say that you shouldn’t race to win: you absolutely should. But you should also be able to be in the moment and have fun with it.

It’s the same with business. I’ve spoken to many entrepreneurs who become so stressed about keeping their business afloat that they forget to enjoy the journey. They work hard to succeed and the daily grind can drag you down. Every entrepreneur knows and understands that. And it’s is understandable, because there are so many things to worry about when it comes to running a business. Sometimes it’s easier to say, “I’ll enjoy myself when I finally reach my goal.” But going about business — or anything — without enjoying the journey itself is bound to lead to undue misery. Where’s the satisfaction of taking that leap if only to let stress drive you?

And that’s where I realized that all of my observations about the parallels between rally racing and business come together.  Don’t be impulsive, but put aside the overthinking. Always strive for your vision, and have co-drivers that you can trust (but know when to trust your own instincts, too). When you keep all of these lessons in mind, it will be easier to relax and feel good about what you’re doing.

Whether it’s learning to drive a race car, starting a business, leading a transformational effort, or navigating a personal endeavor, it’s always better if you can have some fun along the way. Take calculated risks, send the car sideways once in a while to see how it feels, let yourself recover, and enjoy the ride.

When was the last time you realized that you need to stop and ‘switch on’ the fun? Did you ever have a moment where you needed to tell yourself to not just go through the motions, but be present in the moment and open yourself to the adrenaline-rush that you get from this amazing experience of running your business?

Would love to hear your experiences!

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