Mental Blocks and Resource Constraints

Welcome back, it’s been a while since I’ve posted something real on my blog.

This post has a bunch of business honesty and goes into my personal financial situation in depth. I’m sharing it with you to start a new conversation about where I’m going, and to make it possible to write openly from now on about my new path through life.

See my deal with Upload VR isn’t a paying deal. Being entrepreneur in residence just means I have an office there and I have to figure it out. Many of my friends tell me they think I talked myself into a great-paying job and don’t need to worry.


My deal with the founders of Upload VR just put me in place to have a great office in the middle of one of the hottest industries out there (and that’s not me saying that,  great Silicon Valley investor Jeff Clavier told that last week in Paris).

It means I have to come up with a business (or businesses) that will pay enough to keep my family’s lifestyle and, to keep my office at Upload for more than a year, I have to come up with one that provides value to Upload itself. We are in active discussions about that and I expect them to go well. More on that in a future post.

Having an office in the middle of the hottest media business in the world is a HUGE benefit, but all it is is unrealized opportunity. I still need to do the work. I still need to find a way to turn all the coolness of VR and the community that’s coming together into a business. Lots of people want to do VR-related events, for instance, and I have to figure out how to do that while making the income I need to keep my family in Silicon Valley and my autistic son’s many specialists paid to get him the care he needs.

The Upload deal does have other big benefits: I have a media team around me that helps me learn about a new, rapidly changing industry. It has events nearly every night, and is part of a growing market, so opportunities are surrounding me. It reminds me of the early days of blogging where there was the same and eventually the businesses did show up. Techcrunch, Engadget, Huffington Post, all started within a few years of each other due to the opportunity that blogging brought. I believe VR is going to be just as important, if not more so, and it will be followed by an even bigger wave, AR, but the real market might not show up for three to six years. I don’t have the financial freedom to just play VR until the market shows up, so need to find real businesses fast that start paying dividends now.

I can’t imagine a better place to start new businesses than from inside Upload’s offices.

On the other hand, my personal financial runway is running out and boy does that sharpen your focus. Rackspace gave me a few months income to figure it all out and I have until Thanksgiving to build businesses now, or get revenues, before I start digging into my meager savings. I am luckier than many to have even that much time to figure it out, but then my expense flows and housing costs, along with having a kid in college and another who has special needs. His psychologist has been urging us to put Milan into a school that costs $75,000 a year. That is more than a Stanford education for a year! Even now he has dozens of teachers, psychologists, care givers, and baby sitters. Truth be told I couldn’t afford it all even on my Rackspace salary and we are working to cut back but it’s hard to not give your kids the care they need. If you haven’t noticed Silicon Valley is expensive, even for someone with a nice six-figure income.

I remember talking to MC Hammer about why he had to declare bankruptcy: all those mouths to feed. You can get in a financial hole and fast.

I’ve been working on figuring out where my next income is going to come from, but in looking at the problem I realized that I have a mental block. I needed to wash the big-company thinking out of my mind. See, when you are at a big company you start to cruise and you start doing things that don’t necessarily need to add to your personal bottom line. You do things you think are important for your company to be at. You don’t take risks that might help you personally, but might put you in conflict with your bosses. And, yes, even you get used to that fun corporate credit card. Now I find I’m not so willing to go out to an expensive restaurant as I used to be.

I get now why innovation usually comes from a lack of resources. When your family’s future is uncertain staying up a little later and working on your business seems more important than watching a TV show or, even, playing that VR headset (which is why I have two of them sitting on my office floor unboxed). Taking time to meet with yet another businessperson is more important all of a sudden than hanging out with friends (sorry friends). So does taking a tour around the world to meet innovators. All of a sudden you are listening, thinking, and cutting things that don’t aggregate to you. Coming up with business plans. Trying your pitch out on people (and you learn how to pitch again because you have to do it so much where at a big company you only get one chance a quarter to pitch a new idea).

Same when you are working on a technology, or any business really. If you don’t have enough money to do it the old way, you have to come up with a new way to do the same thing cheaper and faster if you want to grow or increase profits. I was talking to the owner of the South African Cycling Team about this, Douglas Ryder. He has two thirds the budget of the other teams. He’s using innovative technology to win. I hope to meet up with his team this week as they race through California to capture his story better but already they have moved from worst to fifth in the world in about two years despite the lack of resources.

I fought with myself whether I should even disclose this to you. After all, there are certain benefits from having you all think I landed a well-paying job and I’m making tons of cash. Sort of like a rapper who brags about his private jet but really is broke. Helps you keep appearances, but I’ve never been one for appearances.

I really only have one thing as a journalist, futurist, or whatever you call me: your trust.

I really have come to hate the social media attitude of “only show the beautiful side of yourself.” I will never treat you that way. Plus, once you start lying, or leaving things out, to your audience and friends in an attempt to get jobs or keep your reputation, well, then you are leading a life that will drive you nuts.

It’s always better to just tell the truth and see where that leads.

I’ve learned the value of asking for help before I fall too deep into a hole. Easier to dig you out of a well if you are only a few feet down than if you’ve fallen all the way to the bottom.

Lately you’ve seen me traveling the world meeting with entrepreneurs, next Monday I head back to Europe to do just that for several weeks. One that I met with recently told me he is worse than broke, his company closed down and now he has a personal debt of a million dollars that he needs to pay back. He’s feeling the pressure I’m feeling but even more intensely. He laid out how he’s digging out of the hole he’s in and that helped me deeply. I know many in the community that are struggling financially. Not knowing where rent for next week will come from. Just knowing there are others going through this pressure does help, which is yet another reason I’m sharing my own struggles.

Some other mental blocks: I thought speaking income might be the way out of this problem, but, no, and even if it were enough speaking is a tough job for a family man. One international speech requires being away from family for five days. This month I will rarely be home in an attempt to rebuild my story and media streams and get around the world to meet many of the influencers in the VR ecosystem, which will probably pay off. Worse, it’s not scalable. There isn’t any way to increase revenues unless you do something else with your life, which probably won’t happen if you are living your entire life on the road.

It’s tough, too, for someone getting older. Even if you get business class seats (which are very expensive) it’s tough on the body and takes one away from building a more sustainable business and is spiky income at best, plus it drives you to do things that might not be natural acts (I arrived to one speaking gig to discover they wanted me to teach a four-hour class to a bunch of MBAs instead of my usual 20 or 40-minute keynote. I’m proud I pulled it off with less than 24-hour warning, but it wasn’t comfortable for sure).

Oh, and if you are desperate for income word gets around that you’ll work for cheaper than your usual retail fee. Which puts your family on a downward spiral. Lots want you to speak for free. The best speakers don’t need to speak to make their money, so they can turn down everything except for the high-paying gigs or the ones that will help their business make even more (which is why most speaking gigs are free, the organizers know you will use it as an advertisement to get business). I’ll keep doing speaking to extend my runway, and for the other benefits, for sure, but doing that keeps me from really working on my business and solving the problem.

Back to mental blocks. I had a mental block about my blog. After all, in an age of Facebook, Medium, Twitter, and Snapchat, why do I need it? I really don’t. I thought. Plus, here I have to worry about security and servers and, yes, even paying for them. Right now Rackspace is picking up the bill but it won’t forever so I need to figure it out. A few years back I was hacked here, which made me realize just how useful having a service is to run your media. Facebook and Medium, for all their failings, protect their users from the underlying work it takes to keep a platform up and running.

It is a mental comfort, though, to have your own space, with your own name on it, that has no competition from others, in which to just share with the world and see what pops out. On Facebook you might not get distributed. On Twitter you might not get seen. On Snapchat you might not get deep. On LinkedIn you might not get read, and even if you do your words are surrounded by distractions.

So I’m working on that mental block. If I’m going to build a media business I need to build it from somewhere I own. I’m CEO and founder of That sounds better than “I’m hoping Facebook distributes me.” I might be broke soon but at least I have something I control. Turns out investor Fred Wilson was right that I gave up something when I left my blog.

All weekend I was hanging out with great entrepreneurs from Silicon Valley, er, San Francisco, including Evernote’s founder, Phil Libin, and one of Product Hunt’s key players, Erik Torenberg, and they focused me on this: build things that you own and that can aggregate back to you and that won’t change. Oh, and they all are trying to find ways to disrupt what already exists. In other words, change the rules. Service Rocket’s founder told me the same recently, he told me to do virtual events to corporate clients. He showed me how one such event would make as much as a speech on the road, maybe more and that it’s more scalable, I could do several per day and to larger and larger audiences. (Service Rocket does corporate training and does it well, has 200 employees and hasn’t taken any venture capital to build that business).

Some things that I do own: my email newsletter. If you are subscribed to that, thank you! (Although Rackspace is currently hosting it, and paying Hugh Macleod to do the art for it, the email is mine and I’ll be moving it to my own business soon). A great reputation that gets me into most any door in the industry. My social graph is full of influential people who continue shaking the industry. My Facebook friend graph has everyone from Travis Kalanick, founder of Uber, to Mark Zuckerberg, founder of Facebook, to Kara Golding, cofounder of Hint Water. I have so many great friends that open up opportunities for me. It’s why I still have a flow of great insights and news from inside companies. It’s why I’m able to recognize trends, like the current move toward spatial computing, before anyone else sees them.

Also, I’m working on another book with Shel Israel, which is about what’s happening next after mobile phones: spacial computing, VR, AR. But there too we don’t have enough money to complete the book. It is expensive to report on, and write books and get them edited and marketed properly. Even just a trip to Magic Leap in Florida will cost us a few thousand dollars. Shel is not in a place where he can invest in the book either, and this lack of resources is causing us to innovate there too.

We are exploring some other business ideas, including starting a consulting/analysis business where we would charge businesses for early access to not just what we’re learning about, say, augmented reality, but where we’d work with said companies on coming up with an innovation plan. Still need more time to figure that out, but Jeremiah Owyang is inspirational here. He has built a nice business that supports his lifestyle without forcing him to be on the road too much away from his family.

We’re considering crowd funding, too, to sell copies of the book, or other partnerships, before the book will come out.

That said, we are willing to hear all creative ideas, including me doing consulting or adding other value beyond just a blurb in the book, and it will be an important book about just how deeply the world is about to change. Heck, tomorrow Google will announce several spatial computing initiatives at its IO conference, but we are between cycles and marketing teams aren’t willing to throw much cash around when this new age will really arrive in two to four years. Timing is hard on products and our book is just a little early. One entrepreneur told me he got sponsors for his conference by offering them 10 days of his time. Great idea, and one we are willing to entertain.

This is what it means to be an entrepreneur: refuse to hear no and refuse to die. That said, damn those mental blocks are sure loud in my head. “You’re going to fail,” they say. I get why it’s so important to get coaching and mentoring to tell those voices of failure to be quiet for a while and to focus your efforts on where you’ll get the most likely chance for success.

Some of my friends and family keep asking “why don’t you go work for Google, Amazon, Facebook or Microsoft or some firm?” I know that’s the easy way out of this problem. I want to build my own thing and get over the mental block that keeps telling me I can’t build my own business. It sure is uncomfortable facing the dwindling savings, though. I am keeping myself from entertaining that mental block for a few more months.

The way I see it is even if I choose the big company path again (or even a well funded startup) I am more useful to it if I have tried to find a new path through life first. I need to build some entrepreneurial skills first to have something to offer another company, if I am forced down that route. For the past month I’ve been working harder than I have worked in two months at Rackspace. Those resource constraints are hugely motivating and that newly exercised muscle will soon be much more valuable than the flab that existed before.

The other thing about going to a big company is that I might end up in this same situation in another seven years. Having to figure out my financial life. But then I’ll be 57 and it won’t be as easy and there might not be two big waves of opportunity coming. The industry is tough for older people. I’d rather have my own business for the last part of my career than have to rely on a committee that I can’t influence for my paycheck.

It gives me a new respect for those of you who have built businesses and, even, those who are struggling to do so. It also shows why the culture you are around is so important. Do you hang out with big dreamers who not only show you it’s possible, but show you how? That force you to focus on business? So many around the world don’t have the advantages I do so end up working at the big company and putting their dreams on hold. Yesterday, on a train, Phil Libin, founder of Evernote, did just that for me. It wasn’t comfortable for either of us, but he was right and I’m so fortunate to have people like that to help me get over my mental blocks.

Over the next few months you’ll follow me as I head down this path to redefine myself and figure things out.

Finally, one person is really inspiring me. Maryam Scoble, I’m her husband. She took a job this year as a conference planner at Service Now. While I’m typing these words at 35,000 feet on the way back from France to home she’s dealing with hundreds of speakers at their huge industry conference in Las Vegas. Why? She’s trying to help me figure this out. She’s keeping a brave face on it, but I can see and hear the strain of a new job with big responsibilities and it has sharpened my resolve to figure it out. It’s really great to have a life partner that’s pulling on the oars in the same direction as you are trying to go, not to mention her job provides health care for the family so that’s one less bill I need to worry about. Plus, as she’s done that I see a sparkle in her eyes of new-found confidence and that makes me very happy.

OK, now that I’ve disclosed the strain, back to work! (Heading back into a plane, this time home to San Francisco, see you in a few hours!)


I’m leaving Rackspace to join Upload VR

The news is now out: I’m joining Upload VR, details here…

What a seven years it was working at Rackspace, much of it as its futurist.

As you know, for the last seven years you’ve seen me hop around the world visiting innovation labs, conferences, startups, and other places/companies that could tell me something about where the future is going. I’ve built relationships all over the world and brought Rackspace to many new companies and places but there are deep shifts coming in our society due to new technologies and it’s time to make a career change.

Not to mention I was one of the most recognizable faces at a multi-billion-dollar public company with 6,000 employees and successfully helped it build its brand on social media and on the world’s most important stages.

Today I’m announcing that I’m leaving Rackspace to join Upload VR — a new media site covering virtual and augmented reality — as its entrepreneur in residence, where I’ll be developing new shows, events, and working with other entrepreneurs in the Upload Collective, a coworking space for virtual reality-focused startups. In particular working with Upload’s cofounders Will Mason and Taylor Freeman.


Well, two years ago, at Web Summit in Ireland, I watched many people get their first look at Oculus Rift. Nearly everyone came out of the demos with a stunned look on their face and most used expletives to describe their experiences. Me too. I’ve seen that happen dozens of times since, including last weekend in Cape Town, South Africa, where a local entrepreneur threw a VR party in my honor and many people got their first experiences with VR, which is why I posted this video as part of this post.

It is clear to me that there are new opportunities to build companies in the VR space (duh, just look at the billions of dollars of investment) and the Augmented Reality wave that will follow VR will be even bigger. I wanted to be in a place where I’d have the freedom to create businesses, or at least be part of a media team that was focused on this future.

In the past six months it’s been clearer and clearer that Rackspace was undergoing its own shifts, toward supporting more enterprise customers who were moving existing datacenters to clouds running at Amazon or Microsoft. VR and AR didn’t yet matter to them, at least not to the bottom line. At least not yet and probably won’t make a difference in the bottom line for three years.

As a media guy, though, I know that in three years the market window will have closed. If there will be new brands, and I believe there will be, or new shows, documentaries, conferences, blogs, worlds, whatever you want to call them, they will all be built in the next three years.
I just didn’t want to sit on the sidelines and Rackspace couldn’t invest in me internally to do such. That’s not how companies work.

So, today, I’m announcing that I’m leaving Rackspace to be entrepreneur in residence at a new media property that you might have heard of. Upload VR is my favorite place to learn about new VR headsets, products, experiences, games, cameras, and more.

I’m writing a separate post about what Rackspace, and, in particular, my boss, Robert D. La Gesse, meant to me over the last seven years. It’s been such an honor to be a public face of a public company and, especially one that has such an important role in the tech industry with hundreds of thousands of customers.

Some QA:

Q. What does Rackspace think of this? Were your bosses disappointed?
A. Rackspace invested in me to go follow my dreams and passions. We both are friends and you may see Rackspace involved in what I do in the future. They also gave me my newsletter, content rights to use as I see fit. This move made sense for both sides. We’ve been working on this for a while and figuring out what my future might look like.

Q. How are you going to be compensated?
A. I’m in a very fortunate position because I’ve been asked to speak to corporate events all over the world. I have a new speaker management company, ODE Management, and they are quite positive that there’s enough demand out there for me as a speaker that I don’t need to worry about that short term and that I can work with Upload easily while doing so. That said, I’ll be working on making a series of businesses, including a new book, “Beyond Mobile” that I’m writing with Shel Israel, so I’ll open up new sponsorship and advertising possibilities in the future. More on those soon. I’m also open to new business opportunities, if you have one let’s talk!

Q. What does this mean for what you are doing on social media?
A. You probably won’t see many changes, at least not soon. My Facebook will keep being full of industry news and things that catch my eye. I will still visit with many entrepreneurs and others, albeit with more of a VR/AR focus now. Same on Twitter, SnapChat, LinkedIn, and Google+. They will get my newsletter, like I’ve been doing the past year. Some changes you might notice is that my blog will start up again and I’m playing with some ideas for YouTube, but more on those later in the year.
One idea that I’m noodling on is doing social media consulting, though. Dale Bracey (he worked at Rackspace on the social media team) and I are thinking that through. A lot of the world still doesn’t understand how to use social media well and Dale was amazing at doing the dirty work of what I call “defensive social media” (helping customers out on Twitter and other places) while I did the “offensive work” of building brand, and building storytelling devices for Rackspace (like I did at Microsoft too). I’m working with brands to come up with some ideas, if you have advice or need that kind of service, drop us a line at

Q. What will my role as EIR at Upload entail?
A. I’ll be working with the Upload Collective team to help find other great startups to join me in the space, along with thinking through its event strategy for 2017. This is one reason why I wanted to join as an EIR, it would give me time after leaving Rackspace to have discussions with a number of companies without the constraint of worrying about appearances. Being a public representative of a public company does tend to limit the kinds of discussions one can have without causing rumors, brand destruction, or stock price consequences, so this change frees me to work with the marketplace on a number of different initiatives. Want to have a chat? Please contact me at or on Facebook at

Q. What will you be doing this weekend at SXSW?
A. I’ll be attending the Upload VR Mixer on Sunday night. I’ll also be hosting a “Beyond Mobile” VIP breakfast for VIP brand representatives on Sunday morning (sorry, that’s sold out). Plus speaking at several events and doing my own reporting on how the VR/AR space is evolving here at SXSW. Am on a panel during the VR day on Thursday with several VR pioneers. Plus having a little fun at the concerts in the evenings and many dinners and parties I’ve been invited to.

Q. Will this mean you will focus exclusively on virtual reality?
A. No. I’m going to continue to cover “Beyond Mobile” technologies, including additive manufacturing, IoT, robots, self-driving cars, artificial intelligence, and other technologies that change our future, all hitting in the next decade. I’m especially interested, though, in VR and AR, and how our culture is deeply changing due to these new technologies. In fact, one advantage of this move is I can spend more time working with Shel Israel on our book, “Beyond Mobile,” which will ship in December. We’re still looking for more sponsors for that, by the way. We’re looking for companies who want to position themselves as leaders in the “Beyond Mobile” space.

Q. Why Upload VR?
A. While most people haven’t heard of Upload, it is my favorite site of those covering the upcoming virtual reality and augmented reality spaces. Plus they have a great office in downtown San Francisco where they are hosting several startups with more coming soon.