50Plus Entrepreneurship Online: the Importance of Authority

Tillamook LIghthouse - off Ecola State Park - Cannon Beach, Oregon

Tillamook LIghthouse - off Ecola State Park - Cannon Beach, Oregon

My series of blog posts on the 50Plus demographic and entrepreneurship have been leading up to the launch of a website. It will be a home for members of the 50Plus demographic who want to understand how to unleash their inner entrepreneur to generate new income streams to support themselves in the extra years many of us are being gifted by living healthier lives. I am creating educational programs and assembling a set of tools and resources to demonstrate how to use the web to generate new income streams with limited financial risk. I want to customize these offerings to the 50Plus experience, needs and state of mind. In my teaching at Lean Launch Ventures I helped teams of Millennials and a few Gen Xers build scalable businesses whereas at the School of Visual Arts I introduced mostly Millennial students to both scalable and micro-business startups. It is clear to me that the wealth of knowledge, talent, wisdom and experience that most of us in the 50Plus demographic possess is the ideal raw material out of which to build a foundation for a web-based micro-business. That foundation needs to be a subject on which you can claim and demonstrate authority

My business will rest on authority I have earned from experience as a serial entrepreneur, teacher, mentor and self-taught student of the web since the early 1990’s. My teaching to date has convinced me of one thing: the greatest impact on students is always "case studies" of real people who had built or were building real things and could talk in depth about their experience. To provide the best education on how to build an online micro-business I will use a range of case studies highlighting some of my micro-entrepreneurial role models. In fact I will begin doing so in this post. My preference is not just to summarize what I have read or learned about them, I hope to provide audio or video recordings of personal interviews with some, if not all, over time. However, I want to go one step further: I am offering myself as an ongoing live "case study". I will show you how to leverage your own history to build a micro-business by putting details of my own attempt on display. There have been other examples of businesses built with various degrees of public exposure which I have studied, but doing it myself for you will be new, not to mention a little intimidating. I intend to structure the site with community elements so we can interact. I want to see the results of the help you get from me. At the same time you will not only see, but have a direct impact on my outcome. We will be in this together.

The key to generating income in any entrepreneurial venture is finding a need and filling it for others, providing something of value they are willing to pay for. The solution may be a product or a service. To understand this let’s start with a simple product, information that people want to learn. Two of my best online role models are great examples that both started by offering valuable information based on authority. The talented Gen-Xer from my new hometown of Portland, Oregon, Chris Guillebeau, author of the $100 Startup had a cameo appearance in my last post. Chris has been publishing for years on his website the Art of Non-Conformity (AONC) which is still his by-line but no longer his primary URL which has been changed to his name dot com. Chris currently describes AONC on his About page as, “a home for unconventional people doing remarkable things.” He goes on to describe himself by saying, “I write books and travel. Over the past ten years I visited every country in the world—but my next quest is just beginning.” Chris goes on to say “the purpose of AONC is to share the story of how to change the world by achieving personal goals while helping others at the same time. In the battle against conventional beliefs, we focus on three core areas: Life, Work and Travel.” In the language of AONC my personal goal for my new website is to launch a micro-business that will help change the world for as many of my fellow 50Plus cohort members as I can by sharing what I have learned.

I have subscribed to Chris’s postings on AONC for years, but I only met him this past spring when he threw out to his readers on AONC the offer to be part of a a class he was going to teach on Creative Live in Seattle. It was limited to a live audience of 10, an interesting mix of Millennials, Gen X and 50Plus because the Creative Live format has teachers "workshop" the issues being covered in class with members of the audience one on one to demonstrate how we could actually apply what we were learning.  We spent 4 days doing 3 shows that were streamed live on the web and 27 others that were pre-recorded for release every week day over the following 6 weeks. Chris is an amazing guy, very focused. Chris exudes authority on travel, the subject of the class in Seattle.  His travel authority is rooted in the quest he set out on to visit every country in the world using the alternative “currency” of airline miles. Chris accomplished it over a 10 year period. He visited 193 countries (he is @193Countries on Instagram), which helped him build an amazing following deeply rooted in his authority on travel, His authority has only expanded over the years, allowing him to develop authority in new domains like life and work.

My second online role model is a Millennial, Pat Flynn. Pat lives in San Diego and describes himself as, “a leader in the areas of online entrepreneurship, digital marketing, and lifestyle businesses”. He goes on to say, “(I) overcame career adversity at an early age by finding [my] own path and true passion.” In 2008 as a recent UC Berkeley architecture grad with a good job Pat got laid off as the recession hit. He was scared and said, “with the economy in crisis, I wasn’t sure how, when, or where I was going to find another job, especially one that I liked. It was all a bit maddening. Then a crazy idea popped into my head: I could work for myself.” Pat discovered that a study-reference blog he had initially started as a means to organize his notes as he prepared to test for an elite industry certification was his path to self-reliance. By inadvertently building a sizable core audience he had established a foothold on the web for himself as an authority in a very narrow niche, the LEED exam for architects, almost without trying. The good news: it became his springboard to a multifaceted career on the web as an authority on online business. [Note: Pat’s original LEED study guide effort still generates an average of ~$2,000 / month in revenue in 2016] Since the early days, Pat described has himself as “the crash test dummy of online business”. His primary business now is rooted in his website Smart Passive Income (SPI) where he has been a pioneer in creating transparency around how online businesses operate. The word transparency is largely rooted in the fact that every month, since October 2008, Pat has published a full financial report of all income and expenses from all of his online businesses, a number of which continues to grow. The report is always a fascinating and highly educational read. He has now catalyzed the formation of an informal cohort that follow his lead in writing this type of monthly report. We will delve into his reports and those of others as we go.

The next question is this: how can authority be leveraged to create income? For now, I would like to emphasize a common denominator in both Chris’ and Pat’s approach to making money online. They both have always given away substantial amounts of valuable information. On his website Chris states, “All of the writing on the AONC site is presented freely with no outside advertising. If you’d like to support the project, pass it on to someone who might be interested.” On Pat’s SPI site he does the same thing but is also transparent on the subject of “affiliate” income that he earns when his readers opt to use tools he uses to run his business. Pat only makes money when his readers make the tool providers aware of Pat’s referral, there is no obligation to use anything that he uses. However, being the “crash test dummy” that he is, Pat tries a lot of tools and generally only uses the best in class. Just to be clear, affiliate income can be earned in a transparent, mutually beneficial manner, and it is an important tool many sites use to capitalize on authority. I will address the full range of ways to generate income on the web in much more detail as we continue our journey.

The important point about both Chris and Pat’s business models is that they both pack their blog postings and in Pat’s case, his podcast and live experiments with Periscope, with an incredible amount of valuable free information. It is not that Chris and Pat don’t want to make money, they just don’t want to do it on their websites through constant high pressure, direct, and in your face, offers. Chris doesn’t report his finances in the same way that Pat does, but in the public domain you can see he earns money from a number of different books he has written, two annual conferences he runs in Portland each summer, the largest, now in its sixth year being the World Domination Summit which drew over 3,000 attendees in 2015, a separate subscription based travel hacking website and more. These all represent income streams that sprang from his authority established via the web that has continued to expand over time into other domains.

I have never met Pat in person, but I am just winding down my participation on a “launch team” of over 400 people out of Pat’s private 20,000+ member Smart Passive Income Facebook group. We received early access to Pat’s first major printed book, Will It Fly, a wonderful treatise on how to validate an idea for a startup, providing feedback along the way. It was released today, February 1. The “launch team” was a brilliant marketing idea that was first introduced to Pat's Smart Passive Income audience in the closing months of 2015 by a guest on his podcast.


It turns out Chris also has another book coming to add to his growing list of titles, entitled Born for This. It will be released April 5th. He too is employing a “launch team” but I am not part of his, having missed a chance to join it. I will cover both of these books in more detail in later posts. Will It Fly is actually my choice of a textbook, or at least suggested reading, for the educational programs that I am creating for the new website. I have used a number of different books over time, but Will It Fly is a classic even before its release. In the spirit of transparency, I should note for my readers that I have no financial interest whatsoever in Pat’s book, I am only an early reader of it, and I am quite impressed by what he has done within its pages.

I intend to pull back the curtain on the new website in February. It is not a finished product, and it still won’t be when I introduce it. It will purposely be a work in progress so that you can see exactly where I am starting, see what I have done, hear what I am thinking and hopefully provide some input on my ideas so I can best serve your needs. I will move most of my past blog posts over to it so that the archive continues to build along with the list of other types of resources. The educational offerings are still being fine tuned, and will take a few more weeks to finalize but I will provide some peeks to get feedback, maybe even form a small launch team for support.


Please subscribe to my e-mail list to keep abreast of future posts and the announcement of the new website.                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                  .








50Plus jobs: micro-entrepreneurs create their own - why wait for "economic development"

$100 Startup Japan Manga Pic.png


"No money, no skill, just a tiny bit of an idea and its good for salarymen, office ladies, students, and seniors."

The book in the picture is the¥10,000 Startup, a 2015 Manga-style, Japanese language translation and adaptation of a very successful book published in English in 2012 by Chris Guillebeau, a fellow Portland resident, best-selling author and life-long micro-entrepreneur. The translation of the banner on the cover, "no money, no skill, just a tiny bit of an idea and it’s good for salarymen, office ladies, students, and seniors", immediately caught my eye. Those words could be the first sentence of my call to arms to anyone in the 50Plus demographic worried about a potential coming shortfall of their financial plan resulting from our unexpected good fortune of living longer than expected.

In a recent blog post, I made reference to current data from BlackRock, the largest asset manager in the world, to estimate the size of the problem facing the 50Plus demographic. The answer: the average Baby Boomer (75 million of the 110 million 50Plus demographic) in the US is likely to fall $36,350 per year short of their own estimate of a $45,500 annual income goal given that they currently have only $136,200 in retirement assets shown in Figure 2. The question stands, can this hurdle be cleared?


Figure 2: from  BlackRock Global Investor Pulse Survey  July/August 2015

Figure 2: from BlackRock Global Investor Pulse Survey July/August 2015

Clearing a $36,350 annual hurdle is achievable for an individual with experience, knowledge, talent and a willingness to work—the key traits of the average 50Plus individual. Chris’ original, English-language version of his book entitled The $100 Startup used the subtitle, "Reinvent the Way You Make a Living, Do What You Love, and Create a New Future", a perfect phrase to complete my call to arms to my 50Plus brethren. Chris was presenting the case for "micro-business" creation based on "micro-entrepreneurship". My only explicit additive would be a simple catalyst: understanding of the power of the Internet to reach almost any other human being on the planet with an offer. That is the basis of success for many "micro-entrepreneurs " today. 

In December 2013, I wrote a blog post entitled “Goal: Job Creation - Scalable Startups vs Micro-Entrepreneur Training.” The $100 Startup was one of three books I referenced. The primary target for the post was my class of millennial students at the School of Visual Arts in the MFA in Design for Social Innovation program. I was using the $100 Startup and Be a Free Range Human - Escape the 9 to 5, Create the Life You Love and Still Pay the Bills, by Marianne Cantwell, to explain the difference between entrepreneurial ventures aimed at launching "scalable" startups, requiring significant financial investment, contrasting them with the "micro-business" model needing, as the Manga translation says, "no money, no skill, just a tiny bit of an idea". Clearly, the first two books carried the micro-entrepreneurship message. The third book I cited was The Startup Owner's Manual by my friend Bob Dorf and his partner Steve Blank which emphasized the “lean” approach to building scalable startups.

A secondary target for the original blog post was government economic development officials. Besides teaching at SVA, I was acting as a consultant to the State of Connecticut’s Department of Economic and Community Development on the creation of a more entrepreneur friendly “innovation ecosystem” in the state. The marching orders of these folks in CT, and elsewhere, is to stimulate the creation of, or the import of, jobs, jobs and more jobs, preferably in fast growing industries. In my experience, when the question of how to do this comes up, the answer reflects economic developer's fondest dream, “we need a Facebook, a Google, an Apple, another Priceline (a CT company), some true high growth companies in this geography. We only need one or two to solve a lot of our job problems”. When pressed as to what they really wanted, the answer in CT was often "just take me to the NY Tech Meetup (where I was active in the Leadership Circle), introduce me to some of your friends and help me steal a few young scalable growth companies".

Lots of public money gets spent trying to seed or create the “conditions” for high growth companies based on the fantasy: they will create the lion's share of the missing jobs. I was challenging this thinking in my 2013 blog post by asking, "why not experiment with some portion of economic development funds by training people to create their own jobs by building micro-businesses"? I pointed out that entrepreneurship is not a genetic trait, it can be learned. Case studies like those in Chris' $100 Startup, Marianne's Be a Free Range Human or about friends of mine who have done it are the best way to teach it. The goal of my challenge: track how many individuals can create their own “jobs” as micro-entrepreneurs by leveraging their existing knowledge, skills and talents mostly via an effective use of the Internet. 50Plus individuals are the perfect test cases for this experiment today. I strongly believe that the “job market,” jobs created by others, especially by "high growth" companies, are not going to be the safety net for the 50Plus demographic. We must experiment. Let's explore the real power of micro-entrepreneurship to understand how it "scales".

This series of posts on the 50Plus demographic has been leading up to the launch of a new website, which I am almost ready to reveal. Historically, I built scalable startups but never a true micro-business. My mission is to build a micro-business in full view, demonstrating to the 50Plus demographic how to leverage one's knowledge, talent and experience, in my case as a serial entrepreneur, mentor and teacher. My goal is to help as many members of the 50Plus demographic as I can create their own jobs. I am not without my own role models. I have been following some carefully over time. They happen to be millennials and young Gen X'ers, folks like Chris Guillebeau, Pat Flynn, Marianne Cantwell and others who took the plunge and figured this out at different points in the last decade and are still doing extremely well. I will hopefully introduce you to some of them along the way. Their stories are amazing. Ours can be too!

If you haven’t done so already, subscribe to my e-mail list to receive notices of my remaining posts in the 50Plus series on this website and the announcement of my new website. I look forward to serving you and getting to know you in the process. Let's do this together!

Serendipity: A Perfect Ingredient to help Solve the Challenges Facing the 50Plus Demographic

   A "serendipitous" four peak day on Jan 10, 2016 near Portland, Oregon on a 2 hour drive never more than 45 miles from my front door all taken from Oregon vistas. Clockwise: Mt. Saint Helens, Mt. Rainier, Mt. Adams and Mt. Hood.


A "serendipitous" four peak day on Jan 10, 2016 near Portland, Oregon on a 2 hour drive never more than 45 miles from my front door all taken from Oregon vistas. Clockwise: Mt. Saint Helens, Mt. Rainier, Mt. Adams and Mt. Hood.

Serendipity was the subject of my first two blog posts in September and October 2013. Both posts were different takes on how we can create our own serendipity. I have been a long time believer in serendipity since I can point to a fair amount of it in my own life. I have had enough of it that I strongly believe there are a number of different ways you can increase your odds of experiencing it. I highly recommend conferences and other well chosen gatherings as starting points since they have been a primary source of serendipitous interactions with people, organizations and ideas that have changed my life. In most cases I likely would not have encountered them in any other way.

In 2015, as my focus for this blog shifted from millennials to the needs of the 50Plus demographic, I hadn't yet thought to touch on serendipity again. It was an article in the NY Times the week before last by Pagan Kennedy entitled Cultivating the Art of Serendipity that put it back on my radar screen. Her subtitle makes a point that caught my eye right away, "Innovation isn't all hard work or dumb luck: It's about paying attention". Kennedy’s timing was itself serendipitous because I quickly realized that I had overlooked that serendipity can be a key ingredient in helping the 50Plus demographic to face its major financial challenges in the coming years.

My message to the 110 million strong 50Plus demographic is this: we have to begin to embrace entrepreneurship to generate the additional income needed to overcome the structural problem of outliving our financial plans. In short, for many, “entrepreneurship will be a necessity, not a choice”. Just to be clear, when I use the term entrepreneurship I start with entrepreneurial thinking. Learning to think like an entrepreneur isn’t based on genetics, it is not a trait that you either inherited or you didn’t. It is a learned behavior accessible to all of us. I am not suggesting it is an easy learning curve, but I can speak from experience as a serial entrepreneur, as well as from teaching others, it can be done.

Tina Seelig, a leader of Stanford University's preeminent entrepreneurship program, provided a definition of entrepreneurship in her book Insight Out. In her words, “entrepreneurship involves building the knowledge, skills, and attitudes needed to see problems as opportunities and to leverage resources to bring ideas to fruition.” In her book, Seelig presents what she has dubbed the four part Invention Cycle. This cycle is  rooted in using curiosity to spur your imagination, which then seeds creativity to allow one to visualize innovations, which finally opens the door to the act of entrepreneurship to bring them to fruition. Seelig doesn’t mention serendipity. However, reflecting on the first part of Pagan Kennedy’s subtitle, “Innovation isn't all hard work or dumb luck”, I would suggest that "cultivated serendipity" is “smart luck”, which I assume is why Kennedy describes it as being, “about paying attention”. I would hold that smart luck based on paying attention is a perfect additive to the Invention Cycle. My gut says Seelig could agree with that.

The 50Plus demographic is loaded with experience, knowledge and well honed skills. Cultivating “smart luck” by paying attention with the right attitude seems like what the doctor ordered to get us on track to solving our own problems. If any demographic can do it, we can.

Having defined the scale of the problem in my last post, coming up with another key ingredient here, in the next few posts in this series I will explain my thoughts on how this all fits together and most importantly why I am confident that if we stay focused we can succeed in controlling our own destinies. It is not too late! I will share more details of my own experiences and those of others, including stories of folks who have cultivated serendipity in various ways to succeed as entrepreneurs. My focus is going to be heavily skewed towards micro-entrepreneurship, starting small to create our own jobs without taking huge financial risks. This is in contrast to trying to fulfill the dreams of economic development officials looking for the next Facebook, Google, Apple or sharing economy startup to create massive numbers of new jobs in their geography. I will emphasize that working smart in this day and age means acknowledging the power the Internet, not ignoring it. A few more posts will take us to the launch of my offering to the 50Plus community based on a new website later this month or in early February. I am excited to share it with you!

Stay tuned a little longer… the meantime please continue to comment here or e-mail me at




50Plus Jobs - facing reality, solving our own problems as entrepreneurs

Let me begin this post by wishing everyone a very Happy New Year. Noelle and I are starting our second year here in Portland, Oregon. 2016 promises to be an important year for us, hopefully for you as well.

Peak of Mt Hood summer 2015

Peak of Mt Hood summer 2015

During this past year, after a long period of teaching millennials how to develop, refine, and implement new business ideas, I began to shift the focus of this blog away from the needs of millennials to take time to build a deeper understanding of the needs of the 50Plus demographic. My last post of 2015 concluded that entrepreneurship is not going to be a choice, rather a necessity, going forward for many in the 50Plus cohort. We are a unique and sizable group numbering over 110 million in the US alone. Thanks to advancements in medical science and an improved understanding of healthy living, we are going to live longer than any of us could have ever imagined during our early working years. That’s the good news! The bad news is the state of our collective finances. A recent report from BlackRock, the largest manager of retirement assets in the US, provides data on our likely future financial position.  These data were taken from the results of a survey of over 4,000 Americans, collected as part of a larger annual global study. Their conclusion is this: 71% of Baby Boomers, the 52-70 year old slice of 50Plus demographic by yearend 2016, are worried about their ability to afford retirement. On average we expect $45,500 a year in retirement income but only have assets of $136,200 set aside today.These assets are likely to produce, at best, only $9,129 per year. That is a huge $37,000 per year shortfall!  Can that gap be closed? My gut says that the "job market" cannot and will not be able to help us with the significant boost we will need in order to achieve that outcome! At best a lucky few will close the “retirement financing gap” through a job created by someone else.

Two articles this past week focused on the state of the job market for the 50Plus demographic, confirming that the employment outlook for 50Plus individuals is weak in spite of a six plus year economic recovery. The first report came from Patricia Cohen, in the NY Times, entitled Over 50, Female and Jobless Even as Others Return to Work. Patricia tells the personal stories of a number of 50Plus women struggling in the current job market. She goes on to cite a US Federal Reserve report and highlights data on 50Plus women trying to return to the workforce after significant time out of it. Today 50% of the women in the 55 to 65 age bracket are classified as “long-term unemployed”, which is double the figure from 2006 for the same age group for women. The situation is better for 50Plus men, but only by a slim margin.

The second article is One Laid-Off Boomer’s Job Hunt: Too Old For This?  by Kevin Kusinitz, a talented 50Plus writer on the NPR website next avenue. Kevin chronicles his own experiences in the past three years looking for jobs. He focuses specifically on the absurdity of in-person interviews, demonstrating the many ways in which the deck is stacked against 50Plus applicants. The bottom line? He hasn’t had any luck. Granted he represents a lone data point, but if you want more anecdotal evidence just read the 1,400 combined comments from both his and Cohen's articles left by 50Plus individuals with painfully similar experiences.

It is clear to me that we can’t hold our breath waiting for others to create enough jobs to put all the 50Plus individuals who want to close a “retirement financing gap,” or who just want a cushion of some extra cash, back to work. This brings me back to my main message in my last few blog posts of 2015. The only shot many of us have is to begin to think entrepreneurially and ask how can we solve this for ourselves. The government and corporate America certainly aren’t going to save us.

I will be launching a new website in January or early February to help fellow 50Plus individuals recognize their inner entrepreneur and to understand ways in which we can leverage our years of experience, deep knowledge and talents to generate new income for ourselves without risking the capital that we do have. All it will take is our time and a willingness to try. We can do it!

Stay tuned.....

All comments are welcome. If you would rather comment privately, e-mail me at Looking forward to hearing any thoughts / suggestions on where I am going with this.