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..)

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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.

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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 this years Web 2.0 Expo in NYC. I was part of the Web2Open sessions that were organized by the Podcamp Foundation (Hats off to Whitney Hoffman), and in traditional “unconference” fashion, those of us who were asked to speak could do so on any topic we wanted.

The theme of this year’s Web 2.0 Expo was “The power of less,” and with that in mind I took this opportunity to do something I’ve been wanting to do for a while, get back to my roots and start talking about my experiences with entrepreneurship, starting a business, bootstrapping, and all of the lessons I have learned along the way…. so far. The Web 2.0 Expo theme was a perfect fit to “beta” a presentation I dubbed: “Bootstrapping: Building a Business Funded by Revenue.”

The Web 2.0 talk was the first step in developing a series of posts and presentations that I will be focused on throughout 2010. Though my story is still very much “in progress,” I have started several businesses, and have been building my most recent company, Blue Sky Factory, for almost 9 years. I’ve learned a wealth of lessons through my experiences building a business from the ground up with zero funding.

The Framework:

As mentioned earlier, the Web 2.0 talk was in “beta,’ as I am still very much flushing out the various topics and segments I would like to cover. As I have been thinking through things, there have been three main topic areas that seem to encompass the spirit of what I would like to talk about. They include the following:

1. Start-up Lessons

Just as it sounds, and what essentially encompasses most of the presentation below, there are oh so many start-up lessons to discuss, and every entrepreneur has their own. Sometimes, more often than not, they all have their own version of the same lesson. I plan on discussing several of the ones that I have experienced and have processed.

2. Building a team

At the end of the day, any good entrepreneur will tell you their company is only as good as its people. It is so true. Over the last 9 years there have been many different people who have joined my company, and each one of them play a key role in our operation. I plan on talking about building teams who are aligned, motivated and constantly executing.

3. Managing growth

It is often said that managing growth is simply the act of trading one set of problems or challenges for the next. There is a lot to be said for that statement. Growth isn’t easy, but if you find yourself managing it, then you are doing something right! There are a several “stages’ of growth to be discussed in a variety of topics (team, technology, infrastructure, finance, sales, etc).

Below, are the slides from the Web 2.0 talk, which tend to focus mostly on the first topic of “start-up lessons.” I would love to hear your input, or questions in the comments below. I will be continuing on this topic organically, and hope to begin to drill down on the high level topics listed above shortly.

I have been thinking about all of the reasons why I have been feeling so good about yesterday’s SocialDevCamp. Its a little hard for me to pin down exactly, but all I can say is that it was an absolutely great event. No, it was a special event. Baltimore has been craving for something like this for years (at least in my opinion).

The event reminded me in many ways of the very first Podcamp in Boston two years ago. There was a clear energy present, and everyone who was there knew it. Yesterday was like that for me in many ways. From the moment I got there until the moment I rolled out of the Brewers Art at the afterparty, it was energetic, passionate, educational and inspiring among many other things. It was great to connect with so many other folks from the area and along the corridor (Boston, NYC, Philly, Baltimore, DC), the Amtrak corridor that is

For the first time in a long time it felt like the Baltimore scene was truly vibing. I know we have all been “vibing” in our own ways, but SocialDevCamp brought a lot of like minded individuals together for the first time ever in our city. Sure there have been small gatherings, happy hours, and definitely lots of great programming by the GBTC to bring the business community together, but this was the first time, that I can think of, where everyone came together. The entrepreneurs, the hackers, the developers, the media, (insert what you are here), etc, it was a collective, and it was a good one.

Thanks once again to Dave Troy, Ann and Keith for organizing this. A big thanks to all of the volunteers, and to all of the other sponsors for financially supporting the needs of the event, and finally thank you to all of the participants for showing up and making it happen. What a turnout!

Here are a few random thoughts from my perspective:

Facility & Location

University of Baltimore’s facility was a GREAT location for this event. The physical space simply worked. There was a main common area where the meals were and tables, the auditorium and the session rooms were all right there. This kept the attendees connected and engaged. It was refreshing to see that there were no sessions on multiple floors, lack of a common gathering area, and basically people all over the place, which is often the case when using university / academic facilities for these types of events. Finally, the actual location couldn’t have been better for out of town folks who hopped on the Amtrak and came from other cities. The UB facility is literally 2 blocks (at the most) from the train station. That fact alone definitely helped with the great turnout.

Sessions & Participation

Although I didn’t participate in the session selection and voting (I showed up a little late), I think the sessions were great. I particularly enjoyed the “Business of Social Media.” What was really great to see was the level of participation from attendees. I know thats the point of these events, and it was definitely present and accounted for. It was great to hear so many perspectives and to learn what was on peoples minds. I sat in the Business / ROI of Social Media, learned about the semantic web, attended Shashi’s session on selling social media to the boss, and the mashed up “who needs VC’s and Amtrak Tech” session. All good stuff.

Corridor concept (DC, Baltimore, Philly, NYC, Boston)

I liked the discussion that was started around linking up the “Amtrak” cities and building off of the momentum of every location. There was a lot of discussion and comparison around startups in Silicon Valley vs. startups out here on the east coast. Discussion around the available resources we have to us, from money to talent and more. The thinking is that we need to start to look at ourselves, out here on the east, as our own corridor or ecosystem, and shouldn’t look at it from a single city point of view. The connecting link between five major markets, DC, Baltimore, Philadelphia, NYC & Boston, is the Amtrak. You can get to any of these cities VERY conveniently via the train, and be in the center of them within a few hours. I look forward to more discussion around this, as we truly are our own technology corridor. Lets tighten this concept up.

In many ways, its great to finally see Baltimore on the map as a micro-hub. I look forward to many more events like this in the future. The next SocialDevCamp is already being planned for this September, details will follow as they are announced. Blue Sky Factory will continue to support these events and any other event that helps bring everyone in our region together.

Here are some links to SocialDevCamp Media: (feel free to add more links in the comments to other media)

Flickr photos

Animoto Slide Show from East Coast Blogging

Video of Sessions by Kenneth

Twitter hashtags

Great to see everyone, catch you all at the next one!

I am still getting requests for the presentation I gave last month at the edu Web Conference. You can download the PDF here. I also just uploaded the presentation to a pretty cool service called SlideShare. You can flip through the presentation below using their widget, and download it from there as well. Thanks to Chris Brogan for turning me on to this service. Very cool.

My good friend via the interwebs, Niccolò Favari a.k.a. flipthedolphin, recently posted an interview with me on his blog. It’s kind of strange having two entrepreneur themed interviews go live within a weeks time. This one was completed well before Gnomedex.

I first met Niccolò in the blogsphere. I don’t remember when, but it was back in late 04 or early 05. You know how it goes, one day he left a comment on my blog, and then I left a comment on his, etc.. next thing you know we are friends from the blogosphere.

Niccolò has been an incredible friend over the years. He was the original registrar for my blog’s domain, he has helped me time and time again with small WordPress tweaks, and many other technical issues and questions. He is also an incredible photographer.

He recently asked me to do an interview for his blog, flipthedolphin. This is in the same vein as the Startup Spark interview with Steve Fisher, in regards to it being about my experiences with entrepreneurship, but the questions are totally different.

You can find the interview at this link.

“…I would say above all else, the one thing that will continually separate successful entrepreneurs and businesses, from others, in regards to momentum and success is their ability to “Execute” The get the job done part is key. People talk a lot, and have a lot of ideas, but in order to succeed you need to always be executing.”

As mentioned last week, Steve Fisher, editor of B5 Media’s Startup Spark blog, and I did an email interview which he began posting this week. Honestly, I had the thing half baked on my desktop for over a month and finished it up on the plane out to Seattle Thanks for your patience Steve!

Steve recently posted part 2 & 3 of the interview. You can check out the series here:

Startup Spark:

Part 1 – Backround, Blue Sky Factory, Competitive Landscape
Part 2 – Vision, Revenue, Team
Part 3 – Elements for success, Bootstrapping, Marketing

Excerpt:

What approach to marketing plays a significant role in promoting and attracting customers to Blue Sky Factory?

Our approach is, we are different. We are not your typical ESP, and you learn that fast. Outside of our search marketing, our ads are different and edgy. I also embrace social media, and I think that’s important as the CEO. As you know, social media brings a certain level of transparency to the company. People get to know me; they get to know the company. We are open, we blog, we are on the social networks, we are speaking at events, sponsoring unusual events, publishing articles, interviewing with the press, being thought leaders, etc. We get a lot of people referring us business simply because they know us. I think all of those things above play a significant role in our marketing and how we attract business.

Its been a pretty busy Monday in our world of email. Check out all of the various activities that have been announced today:

- Constant Contact, the leader in small business email marketing solutions files for an IPO.

- IMN ( formerly IMakeNews) seeks a $30 million -$40 million recap to double in size and do acquisitions.

- Google buys Postini.

- The DMA acquires the Email Experience Council.

A little moving and shaking going on

Below, are some of my thoughts around what I would classify as a “basic” marketing 2.0 framework. I am writing on this topic as I begin to think through the presentation I will be giving in July at the edu Web Conference.

In a very dynamic and ever changing landscape of web 2.0 and social media, marketers are continually faced with new challenges on how to make sense of, and embrace emerging online mediums that expose them to a world of unmoderated, decentralized conversation, taking place within a rich media playing field – syndicated text, audio, and video everywhere.

There are some basic tools that organizations must deploy in order to participate in this complex online social universe. Its becoming increasingly important for marketers to be able to develop and maintain consistent ways of participating in and measuring the success of their online engagement efforts. The ROI on social media will be an important metric for organizations to be focused on as we move forward in this evolving media landscape.

How does an organization measure its ROE or Return on Engagement? What are the key elements that an organization needs to be included in this new social media landscape? What follows is what I believe is a basic framework for participating in a world of Marketing 2.0, or, in other words, marketing in a Web 2.0 world. You will pick up on a common theme as you move through this framework, and that is one of “become a publisher of information.” None of this is rocket science, its pure practicality. We live in an expanding world of content. And yes, content IS king, it was said long ago. Now the mindshare of the masses becomes a content game, down to the marketing level.

Here are some of the basic components and tactics you need to succeed:

A Blog

I don’t really want to spend a lot of time on this one, because if your reading this post, you probably a.) already have a blog and have most likely been writing it for a while, maybe even years, and or b.) you recently launched one or are at least savvy enough to know you need one and are actively working on getting it live.

Simply put, a blog acts as your base. It is your foundation of words, opinions and expressions. Its where you express your points of view, your opinions, your news and information. Its a place where you can revert back to, to clarify your position, stake your claim, and make your mark as a person or an organization. Blogs are the newspapers, the media, the dialogue of the future. To not blog, is to not speak, nuff said.

Email Marketing

Oh yeah, you KNOW I am biased on this one but I don’t have to speak to why email should be a spoke on your marketing 2.0 wheel now do I? Email is the driver, the dominant application of all online mediums. Aside from being an incredible channel for developing loyalty and retention with your audience, the medium also delivers one of the highest ROI’s today for marketers. Email also drives the reach of your message, extending it, and spreading it virally through personal networks and communities. Send out a newsletter, tips, promotions, cross / up sell, re-publish blog posts, link to media, tell your story….build a subscriber base and publish targeted, relevant content.

RSS Feeds

If you are already blogging (or when you begin), you will most likely have an RSS feed associated with your blog. Make this feed as easy as possible to subscribe to for your readers. You may also consider publishing multiple feeds depending on your organization or what kind of content you are publishing. For example, your blog feed, your podcast feed, topical feeds, etc.. Publishing feeds gets your message out via a rapidly emerging channel. Consumers of media are customizing their home / start pages with feeds of interest, loading up their aggregators with subscriptions, and also subscribing to RSS feeds via email as well (another important feature to have). I have a pretty good feeling that an individual’s OPML file will be an important asset as we move forward in this landscape.

Syndicated & Optimized Press Releases:

In short, spread your key news via at least one of these services (PR Web, PR Newswire, MarketWire). The Google juice alone is worth every penny. Get your news, and your name out almost instantly via these syndication services. This is a no-brainer. Yes, it can be costly but for as little as a few hundred dollars to have your news pushed out globally, generating tons of inbound links to your web properties, is really worth the time and effort. I have done it many times and it simply works. Check out the pick up around the announcement of our acquisition of RSSFWD. We used MarketWire’s service for this release.

Produce Audio and Video Content

I am not talking CNN style, spend a $100k on a commercial / promotional piece. Naturally, I am talking about producing podcasts and online video content. Produce something. Come up with a show with a theme that relates to your area of expertise, or your industry. Produce an audio show at the very least, the barriers to entry / production are just too low now to even be debating this internally. Podcast your organizations message, period. If you can add the visual element to this, ie. video then by all means do it, just think it through and make it compelling, unique, relevant and interesting.

We live in a world of online rich media, ever growing and expanding. Broadband adoption has blown this door wide open, giving organizations of every size the ability to become their own media outlet. Broadcast your message in text, audio and video. Again, the barrier to entry is just too low to put up a fight…

Start Speaking and Showing Your Face

Lets get “un-digital” for a moment and talk about humanity and being a real person. We do live in a physical world, and we can’t ever take the human experience away. The personal connection is more powerful than any other medium. In terms of marketing, I believe this is critical. Get out in the world, come up with an idea or a topic to speak on, volunteer to talk to groups, be a guest speaker on a particular topic, be on a panel, go to networking events, etc. In short, show your face and speak your mind. Make yourself the expert in your field and meet and greet as many people as you can. Extend your brand by putting a face and a personality to a name.

As mentioned above, this is only part of a framework. I certainly have not covered everything, and I have not covered or gone into any depth on tactical implementation or measurement. That said, I believe the elements I have listed above are key “spokes” on the marketing wheel of the future, which is now

In an attempt to play a little “catch up” I posted two ROI Radio’s this week. This past Wednesday I posted my discussion with Christine Burke who is the Vice President of Corporate Sales for L’Occitane. It was a great change of perspective having a discussion from the client or company point of view versus the vendor / provider point of view. Christine and I talk about how L’Occitane is implementing a variety of online marketing channels and how they optimize the medium.

As mentioned in an earlier previous post, I also had a chance to speak with Kris Smith, VP of New Media at Room 214, founder of Palegroove Studios and produce of the Croncast. Kris was a trooper, jumping on the phone with me literally with about 2 minutes notice and being asked one simple yet powerful question of “whats next?”

You can check out both podcasts at the ROI Radio site. Subscribe to the RSS feed here. Subscribe via iTunes here.