Welcome to the inaugural edition of my “Angel Series” posts. As promised, I will be writing individually about the companies that I have invested in, both as an individual angel and as a member of the Baltimore Angels.

My first highlight is on Argyle Social, a leading social media marketing platform that helps marketers tie social media to revenue.

Here is CEO, Eric Boggs giving the sub-2 minute pitch:

Click here to view the embedded video.

Why I Invested:

Argyle was an interesting investment for me due to the backstory of my relations with the founders. To me, this is some of the most important “stuff” when an angel makes an investment.

First off, I had known of Eric Boggs and Adam Covati from the email marketing industry, as they had both worked for Bronto. They both did a great job raising their profiles and clearly standing out as emerging leaders within our industry.

My colleague, DJ Waldow bridged the gap in person a few years back during one of the spring marketing conference tours we used to do back in the Blue Sky Factory days.

At the time I was getting to know Adam, I also happened to be looking for a VP of Product Development. There was a very small window of time between Adam leaving Bronto, and starting Argyle. I was about to make Adam an offer, when he let me know that him and Eric were going to make a go at it. As a fellow entrepreneur, I wished them nothing but the best and let them know I would help them in any way I could.

As it turned out, my company Blue Sky Factory, was one of Argyle’s early alpha & beta testers. Adam and Eric spent a lot of time with DJ Waldow, Chris Penn, myself and others on our team, providing feedback on early versions of Argyle Social. Once they launched, we became a paying customer.

What was really cool, was watching them go from 1 to 100 customers in a very short amount of time.

While the Argyle team was cranking away, I was busy working on the Blue Sky Factory acquisition. Once the dust settled, I received a phone call from Eric Boggs who updated me on their traction, and on the details of their current raise and asked me if I would consider being a part of it.

As it turned out, this was the only investment I have ever made without doing deep diligence. Eric and Adam are solid entrepreneurs, with a great offering in a big market, and have my full confidence that they will do everything they can to succeed.

The investment terms were fair for where they were at, and not only did I know the founders personally, more importantly I watched them execute for close to 2 years. I saw the evolution and the traction of Argyle from the beginning.

I also invested because much like Blue Sky Factory, they are a BtoB software as a service (SaaS) player in the mid-market. They play ball with real companies, with real marketing departments who are looking to measure real revenue through social channels. This is almost identical to the experience and market knowledge that I had from my 10 years running Blue Sky Factory. I understand that market very well.

So, in the end, in turns out that Adam and I get a chance to work together after all, just in a completely different way.

I recently gave a talk to a group of students, faculty & staff who participated in Career Week at my Alma Mater, UMBC. The talk was titled: “Blue Skies & Beyond: 5 Lessons from an English Major Turned Entrepreneur.” The theme was “real life after graduation.”

I was not only honored by the opportunity & experience, but it was also an amazing opportunity to look back on life a bit, and think about some of the important things that I’ve learned along the way. The list began to get very very long, so I had to force myself to filter the list down to a few key lessons that are embedded into the fabric of how I operate today.

I also thought about what might be motivational or inspiration for the audience. What kind of information may help them take the next step or make the next move to go for their own WIN, in all of their pursuits.

The talk was probably the most personal I have ever given. Thats not too surprising since it was about my story and my journey. I started from my early days in high school and went all the way through starting & selling Blue Sky Factory, and finished with the efforts that I am working on today. The talk was a great framework for future speeches, and can be greatly expanded on.

So, with that I wanted to share the 5 lessons that I spoke about, with a little bit of commentary on each:

1. Never Doubt Yourself: You are capable of FAR more than you can ever imagine.

When I was in high school, my high school guidance counselor told me not to bother applying to college. Given my performance in high school, he felt I was best suited to attend a vocational school in hopes that I could obtain a skill like an electrician or a carpenter. The theory was, develop some kind of skill set now, so that I would be employable after I graduated from high school. The message was loud and clear, university was not in the cards for me. This was the best advice that my high school guidance counselor had for me.

I’ll never forget the UMBC commencement in May 1997, and the sense of achievement that I had when I personally mailed that high school guidance counselor an invitation to attend my commencement ceremony. Needless to say, he didn’t show up

The important thing here is to realize that occasionally life delivers you experiences when others doubt your abilities, and sometimes, if we don’t persevere in our own right, we can fall into the “trap” of believing those people. This lesson is really about never falling into that trap.

I can only imagine what my life would have been like if I had taken the advice of that high school guidance counsellor.

2. Be Curious: Experience as much as you can.

Many folks don’t know my back story, and the very odd path I took to entrepreneurship. I came to UMBC for an Emergency Medical Services degree (they have one of the best programs in the country). When I was 16, I had been a cadet on my local first aid squad in New Jersey. I quickly became a certified EMT (Emergency Medical Technician) for years before I moved to Baltimore in 1992.

I was two years through the program when I had an epiphany about my life. I quickly realized that I no longer wanted to go down the path of a career in EMS. I pondered for a semester while I picked up some elective courses, then decided on an English degree. My thesis for English, was that no matter what I did in life, I would need to know how to read and write well.

My path to entrepreneurship was a culmination of experiences and exposures throughout college. Think about this: I’m a former student of emergency medicine, turned English major, turned marketing technology entrepreneur. A wild road indeed, and it was a series of events and experiences that exposed me to the people and things that would shape my thinking, interests and ultimately my opportunities.

When I was a student at UMBC, I was busy living and being active in a variety of activities outside of my studies. I was involved with the Student Events Board, a fraternity, held an on campus job as the tech crew manager, was an off campus promoter, etc.. its no wonder I didn’t have a 4.0 GPA, I was busy living at a young age

So, how did I find my way to entrepreneurship? I truly believe that it was my sense of exploration and curiosity, and having a generally open mind that led me to a series of collective experiences that put me where I am today.

As I said during my talk, when I was a senior at UMBC if you told me I was going to start, scale and sell an email marketing company, I would have told you you were nuts

Keep your mind open and always be learning and exposing yourself to new things. You never know where you will find your calling. Keep that sense of curiosity flowing.

3. Trust Your Gut: Your sixth sense never fails you.

When I tell the story of Blue Sky Factory, I’ve been known to say that I ran the company for 10 years purely by my gut instinct. I’m known to say this because its true. All of the constant managing, maneuvering, strategy, developing the vision, thinking ahead, hiring, making timely big decisions, etc.. all of those things as I look back on them were yes sometimes made with the help of facts, but ultimately most were made on my “gut feel.”

I know many great entrepreneurs who feel the same way as I, and in my talk I mentioned the large amount of test data that I have on this

When I look back on the things that never sat right in my gut, or didn’t “feel” like they were in the flow, and also when I allowed myself to be influenced by other people even when my gut was crawling, those were things that ultimately either didn’t work out or had less than desirable outcomes. I am not sure how you describe the feeling I am talking about exactly other than, you just know. Its innate in all of us.

I recommend reading & tracking that barometer closely.

4. Make Bold Moves, Take Risks: They move you further than you could ever imagine.

There is no doubt you’ve heard the saying before, no risk, no reward right? Many of you know that its a true statement. One example I would like to share with you follows: In life, we are presented with a variety of options for our career paths, and much like the earlier thought on continuously nurturing your curiosity, sometimes the comfortable option, or the path of least resistance, is not always the best option in the long run. And sometimes when you DO introduce a little bit of risk and challenge into your life, things can change, forever.

I’ve also come to realize that there are very defining moments in life when you make a decision to either do something or not to do something, and that decision could literally be a fork in the road. The decision you make can impact your future in a very big way.

Before I started Blue Sky Factory, I briefly worked for a startup in the Emerging Technology Center in Canton for a year, it was the only job I ever had after I graduated from UMBC. When I decided to leave that company at the age of 27, I was being courted to join another startup based out of Philadelphia as a regional biz dev rep here in Baltimore. The job came with a $90k salary, a commission plan, and equity in the company. A rather compelling offer for a 27 year old who was making $50k at the time. I was greatly pondering this opportunity versus starting my own company.

Clearly, the job offer was incredible and would have been the comfortable choice and most definitely the path of least resistance for me. It was either that or starting up a business in an absolutely horrible economy with no money, and no chance of getting any investment.

So, what did I decide to do? Of course, I turned down the job offer and started up Blue Sky Factory in one of the worst economic climates (March 2001) with no money, being forced to bootstrap ie. white knuckle it. A defining moment in my life for sure.

Much like the story of my high school guidance counselor, if I had taken the “advice” or in this case “the easy path,” the past 20 years of my life would probably look a lot different. If you are new to my world, the story of Blue Sky Factory ended very well. As for the company in Philly, they closed the Baltimore office a year after they offered me the job, and closed their doors for good a couple of years ago.

In my life, as I look back so far, there were many defining moments based on decisions that were bold and full of risk. In all of our lives we are presented at one time or another opportunities like these. These can be defining moments, ones that you find out what you are made of. So, in short, be bold and take risks! If you continuously play it safe and take the path of least resistance, you are going to be leaving a lot of personal growth, self discovery and overall awareness on the table when it comes to life. Just my personal $0.02.

5. Stay Humble & Have a Sense of Mission

“Check your ego at the door.” You may have heard that statement before as well, and I have found that its a very POWERFUL statement as well as a POWERFUL practice, and has served me well in both life and in business. Lets face it, no one really likes to be around with someone with a big head or who comes across as if they are above everyone else in the room. I call those folks “Oneupsmen,” No matter what, they are always bigger and better in everything being discussed and their head is BIG.

There are many lessons in life, and in business, and I believe if you take each of your lessons to heart, they should ideally lead you to a state of humility. You should continuously be in a state of thanks and humility for every lesson you receive in life. My life’s work currently is focused on helping other entrepreneurs achieve their dreams. I take the lessons very seriously, experience & knowledge gained is critical in every situation.

When I think back on my early days at bootstrapping Blue Sky Factory, and what I learned from the UBER lean days, when there were just a few dollars in the bank, and when often there were no dollars in our pockets. Back when we lived on peanut butter and jelly sandwiches, and the mere thought of taking out our then girlfriends, now wives, couldn’t even enter our minds as a possibility. Times like that will humble you. You don’t forget, nor should you. Give thanks for everything you have no matter what, and try to help others achieve their dreams if and when you can. In short, karma is what karma does.

This was the overall theme and thesis of the 5 lessons that I chose to share with the audience at UMBC. I had about 12 pages written out and I read, off paper, for the first time, a very personal speech that gave a little insight into the fabric of this entrepreneur.

The feedback overall was great, and I enjoyed talking to the future generation for quite a while post-event. In closing, these are just some of my truths based on my own experiences. My only hope is that some of the above either inspired or moved you in some way. I would love to hear your thoughts, reactions and additions in the comments. Thanks always for reading.

Another writing initiative that I’ve been looking forward to getting started is a blog series on my angel investments. I’ve been an active angel investor for the past three years, and currently serve as the managing member of the Baltimore Angels group.

Why? Simply, I’d like to highlight and talk about the companies I’ve invested in, and more specifically, why I invested in them. I want to do this in order to present a layer of angel exposure that I wish there was more of. I don’t pretend to be someone who knows it all, or has the crystal ball etc.. In reality, though my personal experiences in entrepreneurship were always bootstrapped, I’ve helped many startups raise a LOT of money over the last few years.

Over the next several months, I will pepper the blog with a highlight of one of the many companies I have invested in. To date, my portfolio consists of the following companies below, and in no particular order I will be writing about each of them in individual posts.

Thanks for reading, and I hope you enjoy the series.

As promised, I wanted to take a few minutes and do a recap of all of the exciting things that have been happening in Baltimore since I wrote my post “The Entrepreneurial Ecosystem” back in November. In short, LOTS has happened.

First, I would like to briefly follow up on some of the things that I’ve been actively involved with in the ecosystem, and give updates on each. I mentioned three areas where I was helping to contribute, GBTC, Baltimore Angels, and an accelerator. There have been significant updates with each:

Greater Baltimore Technology Council (now the gb.tc):

I am not sure where to begin here because there has been SO much velocity with the gb.tc since December it feels like a completely different organization, because it is. In December, we had new leadership come on board, Jason Hardebeck, who took the reigns and starting blowing things up almost immediately. The gb.tc gave up its office, has embarked on the #nomorebox tour and is co-working out of its members offices in an effort to stay connected to its members and core constituencies.

The gb.tc also was the first tech council to give up its membership dues and become an open platform. The group is now supported by investors, which also include sponsorships and event revenue. Speaking of events, in 4 short months the organization has put on InSquared and BmoreFail, and supported many other activities and initiatives in the region. I mentioned to a group recently, that the gb.tc is now curating our community’s stories, and is a facilitator of support for all movements in the Baltimore technology, entrepreneur and innovation community. The gb.tc really is becoming the connective tissue in this region, and thats exactly what Hardebeck wants it to be.

I look forward to continuing to serve on the board and help to advance this organization.

The Baltimore Angels:

As mentioned in my last post, I starting running point for the Baltimore Angels at the end of November last year. I am very proud to report back that we have made incredible strides in rebooting this group into a very active and vibrant organization. First, we are now a membership based organization with 42 active and engaged members. We have successfully implemented a pre-screening process for our deals, are meeting on a monthly basis, have active sponsorships, and a partnership with TEDCO to help with due diligence and closing services. Most importantly we are funding startups! Since December the group has funded Parking Panda, Dinner Time, and is at the time of this post, finalizing its second investment of 2012, another local Baltimore startup.

In short, I am excited to see the commitment to this group. The flow of activity and the monthly meetings are getting better and better, and our group is growing every month. I am glad to have been able to help reboot this important function in our region. I also appreciate the help of Ed Chalfin, Sean Lane, Dave Troy, Jason Hardebeck, Lisa Dubaj and many others for helping me get things organized.

In addition to the Baltimore Angels, the new “Propel Baltimore” fund (mentioned below), is also active and ready to fund startups in Baltimore City. The combination of the angel group being active, and this fund coming online greatly shift the landscape for early stage capital in Baltimore. This is a very good thing for the entrepreneurial ecosystem.

Startup Accelerator = Betamore

I mentioned in my earlier post that I was working on developing an accelerator in Baltimore. This was also picked up in the press as well. Since the publishing of my post and the Sun article, the concept has changed greatly, and without going into a lot of details yet, I am proud to announce that Sean Lane, Mike Brenner and myself have teamed up to bring you, Betamore. Betamore is an urban campus for entrepreneurship and technology. Think education, incubation & community. Thats all I will say for now, but you should drop your email to stay in touch, and look out for an opening sometime this summer.

In addition to this brief update on the efforts I have been involved with, my friend, partner and overall Baltimore rockstar Mike Brenner recently announced some exciting news about his site Startup Baltimore partnering with Technically Media out of Philadelphia. This is another important step in creating a vibrant ecosystem here, a media organization truly dedicated to covering all of the great things happening in our city. We need more than just Gus and citybizlist out there They can’t do it all!

If I was going to wrap up some of the other happenings of the past few months, I would just be regurgitating what Mike outlines in his post below:

Other Baltimore Regional Updates from the Startup Baltimore site:

AccelerateBaltimore has Announced its Inaugural Class of Startups
The four startups that have been picked are: Flying Pig Digital, Hooopla, NoBadGift.com, and Unbound Concepts. The accelerator is being run by the ETC in Canton, made possible through a grant from the Abell Foundation.

More info: http://bmo.re/GZBRBw

Startup Maryland Launched on March 30th
Startup Maryland launched its effort to ignite entrepreneurship at a kick-off event March 30th at the UMD Entrepreneurship Invitational.

More info: http://bmo.re/GZHPCl

Loyola has Partnered with Wasabi Ventures to Launch Accelerator
Loyola University Maryland announced the initiative which will create a forum for the University to collaborate with local entrepreneurs interested in creating and building new businesses. The accelerator will be located in the Govans community in North Baltimore, just east of Loyola’s North Charles Street campus.

More info: http://bmo.re/HmGa9y

Blackboard has Acquired Moodlerooms
Moodlerooms, one of the world’s largest open-source education service providers and graduate of the ETC in Canton, has successfully exited out of “startup” status through this acquisition. Now located in Federal Hill, Moodlerooms intends to keep their name, continue to operate independently, and most importantly stay in Baltimore!

More info: http://bmo.re/HkkO8z

Gov O’Malley Announces InvestMaryland, an $84 Million Fund For Maryland Startups
Maryland is the first state in the nation to use an online auction to raise funds for the venture capital program, InvestMaryland, which will deploy the first round of funds to seed early stage companies this summer.

More info: http://bmo.re/H4dCRy

ETC has Hired Deb Tillett as New President & CEO
Ann Lansinger, who has run the ETC since its creation in 1999, is retiring this year and will be replaced by the veteran video game industry executive.

More info: http://bmo.re/Hu5gzY

Digital Harbor Foundation has Created the EdTech Link
The Digital Harbor Foundation has announced the EdTech Link, a program and fellowship opportunity linking teacher professional development to student after school programming in the areas of technology, innovation, and entrepreneurship. The program will begin in June 2012.

More info: http://bmo.re/Hu6F9q

Abell Foundation and TEDCO have created the “Propel Baltimore” Fund
The fund, which has now reached $4.3 million, will pump needed capital into Baltimore city startups. TEDCO will start accepting applications on April 2nd.

More info at: http://bmo.re/GZRx5i

Not a bad little spurt of activity here in the Baltimore region eh? I think more has happened in the last 6 months than in the last 6 years Its great to see a community of DOER’s out there making things happen. This is only the beginning and I am SURE I didn’t cover everything. I wanted to fulfill my promise of following up and keeping folks in the loop with the development, and evolution of the ecosystem here in Baltimore. I am working on a more specific second version draft of “The Entrepreneurial Ecosystem” in general and will be publishing that soon.

Thanks again for reading and of course, please feel free to comment and add your take on things, and add anything of note that I may of missed.

Welcome to the soft launch of my newly redesigned and rebranded blog. Its been a work in progress, but we are finally on the other end of getting it done.

Big thanks to my friends at WeFixWP for hacking through this and to my good friend Trevor Steinbacher who banged out a few cool new headers for me to rotate through over the coming months.

A couple of things are still in motion. First, I have switched to a new commenting platform called Viafoura. As a result, all of the old legacy comments have not yet been ported over to the platform yet, so please be patient. That said, feel free to comment away on any post. Viafoura is up to some really good stuff.

If you are a subscriber to my RSS feed or receive my post via email, I will be moving my feed in the next day or two. I will try to forward or redirect the old feed, but if you are interested in the new source feed its: http://feeds.feedburner.com/gregcangialosi

I will also be adding a newsletter to my mix.  Currently, on the blog if you sign up you will just receive my posts in your inbox, this will be separate from the newsletter which I plan to launch in the next month.

Thats pretty much it for now, hope you like it and I appreciate your patience as things may still need a tweaking or two.

Thanks for tuning in.

Howdy! Quite a bit of time, and more importantly, exciting things have happened since the last blog post here on The Trend Junkie. I am eager to tell you all about them and fire things back up on a regular basis. I hinted towards the end of the last post that I planned a reboot of the blog, and now, 4 months later, that is about to happen.

Over the next week I will be transitioning from The Trend Junkie domain to my last name, cangialosi.net. All existing posts and links will be redirected to the new domain. I am pumped, as this is a project I have had on my mind since this past fall. We all know its all about execution. My good friends at WeFixWP are hard at work building out my new custom theme and porting over the content. I can’t wait for the new version to go live!

Once I go live, I will kick off with an intro post followed by a post on all of the exciting things that have happened since November 30th when I published “The Entrepreneurial Ecosystem.” My head is spinning just thinking about all that has transpired, and my drafts folder is filling up with stuff to write about.

More to come. Time to reboot and refresh! Until then!

I’ve been holding off on my writing until my new blog is finished (cangialosi.net), but things are taking a bit longer than anticipated. In the meantime, I’ve been accumulating topics that I want to start writing on and figured why wait, everything is going to get ported over to the new blog anyway.

It has been almost 5 months since I sold Blue Sky Factory. Since then, I’ve transitioned myself out of the day to day of the business, spent a month in NYC, traveled for weeks in Italy with my family, spent a ton of time trying to help reboot Baltimore’s local tech council, completed a consulting project, completed a handful of angel investments, and have finally settled back into Baltimore and have begun thinking about whats next. Along the way, I’ve spoken with many entrepreneurs, investors, & visited a bunch of startup accelerators & incubators, and have been thinking a lot about the entrepreneurial cycle, and how it relates to the creation of entrepreneurial communities.

This is a topic that I have been giving a lot of thought to given my recent exit, especially as it relates to my hometown of Baltimore. In Baltimore, we seem to have this void of a truly functioning entrepreneurial ecosystem, yet we have all of the pieces of the puzzle, right here, right now. I’ll add some color to this later in the post.

The Entrepreneurial Cycle:

First, lets define the “cycle.” In my mind, the entrepreneurial cycle is the experience of starting a company, scaling a company, and successfully exiting (selling) a company. These events can be both large and small (both in size and scale of the company, and the financial implications), and take anywhere from months to decades to complete. In some cases, the experience comes with investment, and for others, like myself (this time around), bootstrap with no investment and grow organically. The experience comes in many different flavors.

So, What Happens Next?

Every entrepreneur takes a different path in the cycle of entrepreneurship. However, one of the big questions about the cycle is, WHAT HAPPENS AFTER AN ENTREPRENEUR EXITS?

A few, but certainly not all, of the answers to this question I’ve learned by talking to and watching others who have been through the cycle are as follows:

- They start another company (this is the most likely outcome)
- They start angel investing.
- They get involved on philanthropic or activist levels.
- They start consulting or get a job (unlikely but it happens).
- They tune out and fade out of their community.

In established entrepreneurial communities, this is a bit of the norm for an entrepreneur. However, these actions in non-entrepreneurial communities add value, but can often be a missed opportunity to help create, nourish and sustain an entrepreneurial community. Certainly, starting another company and or investing in other companies are a good thing, but these actions can be much more efficient when there is a proper ecosystem in place. This takes time to build.

What is an Entrepreneurial Ecosystem?

I am talking about an ecosystem that attracts and supports entrepreneur’s at every stage of their growth. A community where there is an abundance of: co-working spaces, startup accelerators, incubators, local and state support, involvement from local colleges & universities, vibrant community organizations, amazing events that celebrate this ecosystem, and clear bridges to the funding community at every stage of a company’s growth.

To me, a functioning ecosystem for entrepreneurship looks like this:

Nucleus Layer: Where idea’s, connections, partnerships, co-creations happen.

Enablers: Co-working facilities, community events (Startup Weekends, Hack-a-thons, meet-ups, association & membership events, etc..)

______________________________________________________________

Innovation Layer: Ideas go from concept to reality. Making things happen.

Enablers: Active angel & seed investing community, startup accelerators, bootcamps, incubators, etc…
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Growth Layer: Building the companies in our ecosystem – a pathway to growth.

Enablers: Active regional venture capital investment & local & state participation in financing.

______________________________________________________________

Sustainability Layer: Keeping the entrepreneurial wheel turning.

Enablers: Active & syndicated angel investing, state & local programs to facilitate and stimulate activity. University entrepreneur programs & support networks. Entrepreneurs giving back and feeding the overall ecosystem.

______________________________________________________________

Entrepreneurs that come from entrepreneurial ecosystems help to continuously plant the seeds of the next generation through mentoring, angel investment, assisting in associations or groups that support these efforts, and by ultimately launching another company.

This kind of functioning ecosystem is currently missing in Baltimore. All of this is here, but we still need to connect the dots.

Building the Ecosystem:

Brad Feld said it best in his recent post on building entrepreneurial communities, and that is that there are leaders and there are feeders. Let the entrepreneur’s be the LEADERS, and have the FEEDER’s encourage and support them. Taking the long view (as Brad says 20 years), this is definitely the right approach. This type of community doesn’t happen overnight. However, there are things we can do to accelerate the process.

So, for communities, like Baltimore, that have all of the “raw materials” right here, right now, the best thing we can do to start threading the community together is to give back and focus on the areas that need input and action. Building the layers of that ecosystem and linking them together is the hard work, and the work that takes the time.

In my opinion, this type of activity is not only what Baltimore needs, but is what this country needs, now more than ever. Simply put, the building of entrepreneurial communities keeps the economic wheel turning. On a macro level, I’m talking about economic development, job creation, etc.. We all know these things stem from the entrepreneurs who start companies, innovate in industries, and make things happen. The more support we offer the innovators, the more innovation will occur. How many jobs have been created in NYC or Silicon Valley over the last 5 years? Lots.

There are several entrepreneurial communities that already give back to the ecosystem that supported, nurtured and grew them over time. However, we need this kind of participation on a MUCH wider scale. We need it in the secondary and the tertiary markets just as much as the major ones.

How Am I Contributing Locally?

I’ve always been a doer, and so understanding, at least through my eyes, some of the challenges that we are facing in my hometown of Baltimore, its hard to complete the cycle and just sit on the sidelines to see “what happens next” in our community. There is a lot of blocking and tackling to be done in our city – and I suspect many cities all over the US and internationally.

So, what am I doing to help further develop the entrepreneurial ecosystem in Baltimore? Here is a start:

Baltimore Angels:

As of mid November, I’ve officially taken point and am helping to lead the Baltimore Angels group. We are a loose group of angel investors who have been active for the past 2 + years and have done a half dozen or so deals. The group just went through a slight lull in meeting due to great things happening, like the main organizer, Dave Troy, raising almost a million dollars in funding for his new startup 410Labs (disclosure: I’m an investor). The group was in need of some renewed focus and some additional structure, so thats what we are doing. In 2012, the group will be meeting every month and collaborating with other angel groups and growth stage venture capital firms, and other supporting organizations within the region to ensure we have an active angel investing function in the city / region of Baltimore.

Startup Accelerator

One of my passions is being at the intersection of ideas and watching them come into reality. Its a big reason why I named my latest entity Nucleus Ventures. I like to be close to the nucleus of ideas, where the raw energy of making something happen is taking place. The startup accelerator model is nothing new, but has gained traction all over the country and the world. Long story short, we need one in Baltimore and I am working diligently to try to make that happen in early 2012. I am hoping that we will be able to create a space and a program that will attract the best and brightest entrepreneurs to come to Baltimore and make their dreams a reality.

Greater Baltimore Technology Council

I am convinced that now more than ever there is a need and a role for a local technology council. In Baltimore, ours has been going through a large transition. We’ve had leadership changes, staff changes, and an overall change in the need the community has for the tech council. I am a co-vice chairman of the council and have been spending a lot of time helping the staff, along with other board members renew the value proposition and membership model of this organization. My hope is that the tech council will renew its value proposition to the community, and take advantage of all of the amazing inertia points that we have happening in Baltimore. The GBTC is a connector, a facilitator, and needs the support of the local community to thrive.

So, that’s my perspective on entrepreneurial ecosystems, and my take on where we stand today in Baltimore. What do you think? Am I off base? These are the things I feel need to happen in our communities to make them entrepreneurial.

I would love to hear your take. Comment away, and as always, thanks for reading.

Its been close to two months since my last post, and wow have there been some changes. I promise nothing too long winded, but let me catch you up with the highlights of the last month:

First up, if you are not already aware, I sold my company Blue Sky Factory to email marketing leader WhatCounts. After 10 years, its a wild experience to finally be an “exited” entrepreneur and have completed the cycle. I am very proud of the company we built, the presence we had in the market, and the kick ass team that I have had the fortunate experience of working with over all of the years. Every single person, past, present and future has played an important part of Blue Sky Factory.

As I mentioned in our final blog post:

It’s hard to fully express how strongly we feel toward our customers and employees. We’ve worked hard to build a profitable and thriving business and are proud of what our customers have been able to accomplish. It’s been a labor of love, and we are grateful we have had the opportunity to work with you as we developed and built Blue Sky Factory. Once again, thank you for your continued support and for joining us as we begin a new and very exciting journey.

Here are links to the video, announcements, and press:

Press:

WhatCounts announcement
Baltimore Business Journal
ClickZ

Here are two interviews I did for some additional perspective:

“After Blue Sky Factory’s Sale, Cangialosi Looks to Help Baltimore Entrepreneurial Community”

“When to Sell – A Conversation with Greg Cangialosi, Former CEO of Blue Sky Factory”

There are a few other flavors as well if you are interested on this Google search.

As a result of the acquisition, I am no longer an employee of the company and have moved to the board of directors of the combined company and will be doing some product strategy work for them on a consulting basis. Pretty exciting times to say the least! Definitely life changes.

So, what’s next?

Well, after running a company for the last decade of my life, the most sound advice I have been getting is “Take a break!!” For me, its really hard to be going 150 mph and to jump right down to 50 mph. So, the short answer is I am winding down many of my day to day affairs at Blue Sky Factory and helping to wrap some of the transition work that is part of an acquisition. As far as what’s next, I am going to give it several months before I jump back into anything serious or semi-full time. I need to clear my head, and take advantage of this opportunity in life and enjoy some time with my wife and daughter, that is just too precious of an opportunity to let fly by me.

Angel Investing:

Outside of some volunteer work I am doing with organizations I am currently involved in, the only other thing I will be actively be participating in is some angel / seed funding. I have been an active angel investor for the past 2 years and am now starting to ramp some of my activity up. If you think there is something I should take a look at, I would love to hear from you. I will also be writing a little more on this subject as I am investing within specific criteria. In the meantime, feel free to email me at gcangialosi at gmail dot com.

New Blog:

Over the next month I will also be transitioning this blog from The Trend Junkie to a new domain – cangialosi.net. I will announce it when its live but stay tuned for a complete redesign, and my attempt at writing on a regular schedule. I have learned a wealth of knowledge over the last 10 years and in particular the last 6 months. I have attempted to share a lot of my entrepreneurial experiences here on this blog, and will continue to do so in the future.

Thanks again for reading and I look forward to staying connected.

I recently had the opportunity to speak at the first Personalization Summit in Mountain View, CA. I was on a panel called “Personalization: Why its Happening Now.” Since I “Evernoted” some of my thoughts in preparation for our panel, I figured I would post an excerpt here in the hopes of getting others perspectives and opinions on the personalized world that is emerging very quickly. Below are some of my notes on the first, high level question we discussed:

How will the world be more personalized in five years?

From a marketing perspective, we have been in the evolution of personalization for years, and even so we are still at the beginning of what I think will be a HIGHLY personalized world in the very near future. Like anything else, it just takes time to get there, because in my mind all parties involved in the personalization revolution must be aligned, and clearly there are still many moving parts around this.

The obvious advancements in personalization in online marketing will continue in the areas of personalizing website experiences, email marketing, social media properties and of course one of the biggest, mobile. I think those three channels – email, social and mobile will be the most active in accelerating the personalization revolution. We are in a world now, where data is BIG. Think about the amount of data that is being generated every single day. Every web visit, every “like”, every “tweet”, every “check in”, etc they all say something about us.

The obvious advantages for personalizing marketing are clear – these channels are delivering incredible ROI, and the data backs up the fact that the more relevant i.e. personalized the message, the better the overall conversion rate. Its simple, think about the conversion rate on a highly segmented daily deal email (Which really hasn’t started yet, outside of location segmentation), or taking the amazon shopping experience to the next level. Now, and in the future, a lot of this will be driven by purchasing intent / peers / influence from a consumers social graph.

Even some of these channels are beginning to go through a personalization revolution – think about the mobile social network Path with its 50 person friend limit – its personalizing the social network. Where facebook is really a list of friends, Path is a network of people you really care about.

We are also going to see a lot of personalization in the offline world as well. There will be a level of personalization on so many things that are just starting – think about travel, auto, clothing, banking, etc.. you are starting to see all of these industries and markets are beginning to personalize products and services in the general sense. One example I discussed was the loyalty program for Kimpton Hotels, as a member when I go to any of their properties, I know when I check in they know I want a high floor, away from the elevator, a certain type of pillow, and the NY Times & Wall St Journal at the door in the morning. Everytime I visit a Kimpton, they simply say “We have your InTouch number here on file” and I know the experience will be the same – that is personalized travel.

Personalization clearly has its advantages. Today, think about how we are constantly being bombarded by media waste that is irrelevant to us. Imagine a world where there is very little to no media waste? It wont be in 5 years but in 5 years there will be a lot less of it.

I also think that more and more brands will continue to shift to implementing personalized communication preferences for consumers. I am talking about the uber preference center / ultimate in personalization across all channels. Let the consumer be in control over what messages they get, on what channel (email, mobile, social, etc), and on what frequency.

Challenges:

The challenges for a streamlined personalized world are vast, and we are seeing lots of moving parts as I mentioned earlier. One of the main issues is that there is data all over the place on consumers, and they are not in control of it. Consumers should be able to own and potentially even monetize their own data, almost the same way they should be able to ultimately control how they are communicated to as I mentioned above.

We are seeing a lot of new innovation and even industries trying to tackle the issue – check out Personal.com for example. This new startup offers consumers “data vaults” that you can share with whoever you want – friends, family, or companies. Once you link up things like this to data exchanges, where the consumer is in control of what they want or are looking for, it becomes a very personalized world. Probably not 5 years out, but I think that this may be where it is going. The question is can there be one place where the consumer controls all of their data?

Privacy & Compliance:

As mentioned, a big issue is that there is so much data about consumers in SO many places. There is no true over site, so that’s one of the nuts that has to be cracked. If industries don’t self regulate on issues like this, then the government steps in and regulates the industry. The bottom line is that the federal government is getting involved and proposing various regulation around this space.

There are obviously large threats that need to be considered, outside of general security, there is also a high risk of identify theft and being able to reconstruct an identity from a variety of data sources, among many others.

In my opinion, we are going to need to go through a real consumer education process on personal data online and make it simple for people to understand. To date, consumers don’t know whats going on out there, and are continuously not included in the conversation. The consumer issues don’t only lie with facebook privacy concerns with 3rd parties. There is a much bigger picture out there. I am not sure how it will all play out but one thing is for sure, personalization is inevitable, and we are only at the beginning stages of its evolution, and its creating a whole new horizons of companies in the space.

Those are some of my thoughts on the future of personalization. I would love to hear what you think and expand on this. Thoughts, opinions, rants in the comments below please. Thanks for reading.

Greetings once again! As the first long awaited follow up post on entrepreneurship and bootstrapping, I wanted to first address the topic of whether or not bootstrapping a startup is right for you. Many of you who know me know that bootstrapping is my preferred method of building a business. In reality, its all I know. That said, I realize bootstrapping is not for everyone.

In this post I will cut to the chase as I have written several posts on the topic in the past. The main themes are pretty direct and are based 100% on my experience. So, let’s get down to the title of this post, is bootstrapping for you?

Tenacity Required: This is not for the faint of heart.

It’s safe to say that starting a business, any business, is not easy. Starting one with limited funds makes it that much harder. That said, many entrepreneurs, like myself, go for it without raising any outside money. However, I’d like to briefly clarify what I define as “bootstrapped,” as there seems to be some fluctuating definitions out there. To me, you truly are a bootstrapper if you:

- Did not raise a DOLLAR of investment (of any kind).
- Used existing savings or your own personal funds to launch.
- Used credit cards or existing credit vehicles to fund your business (bank loans, etc)
- Sweated out the start up phase and made it work.

You are NOT a bootstrapper if you’ve:

- Raised friends and family money (No, you didn’t bootstrap, you raised money)
- Raised angel investment, venture capital or private equity money of any kind.
- You get the point…

Bootstrapping to me means five simple, yet tough words: You Are On Your Own.

This is a position that many people are not willing to put themselves in. And believe me, I completely understand why. In many cases, you need to be willing to risk putting it all on the line, which is a lot to swallow. This varies of course depending on where you are at in your life. When we started Blue Sky Factory, I was 27, single, with a very simple lifestyle, and I had the “what do I have to lose, this is the time, lets go for it” attitude. Today, I am married with a 2 year old and a mortgage. For some folks, those factors alone are enough to reconsider entrepreneurship altogether, especially bootstrapping a business.

While there may be higher risks to bootstrapping, the good news is that today you can launch a startup very light if you are doing a tech startup or web app. Look at what Graham Lawlor’s Ultra Light Startup’s is doing in NYC and Boston. This is the modern day startup ethos. You can launch light and in more cases than not, there is no need to put it all on the line!

Be Relentless: You must BELIEVE:

There is a common trait in many of the successful entrepreneurs that I know. They act as if failure is not an option. This is a simple yet very powerful trait. The BEST entrepreneurs will work at it until they get it.

As an example, when we started Blue Sky Factory back in 2001, we were a “web shop.” Which back then translated meant we would do anything (web related) if the check cleared. If we couldn’t do it, we would find people who could. We hustled and struggled our way through the pure startup phase until there was some sustainability (i.e. revenue). It was raw, but we never stopped believing and quickly pivoted into a pure play email marketing company (we don’t build websites anymore).

The point is, although at one point we had less than $100 in the bank (yes, you read that right), we kept going, relentless, where many others would have given up, we rode the fiber that held it together and moved the ideas and the business forward. Failure to us, was not an option, and it its not to the best entrepreneurs out there. In my mind all great entrepreneurs have to be optimists, all of the time. Frankly, there is no other way to be.

So, the real question to any prospective boostrapper is as follows. Even though the landscape has made the startup barriers easier and less risky, if you do kick off a real business are you in the right frame of mind, and do you have what it takes to power through the tough times with the FULL drive that failure is not an option? Simply said, are you ALL IN?

The rabbit hole on boostrapping goes much deeper, and I plan on writing more about the subject, but that’s all I have right now. Please share your thoughts, comments, opinions, etc in the comments below, and thanks for reading.