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.

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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.

There really is no time like the present. In today’s landscape, things are changing around us all of the time. The most successful organizations operate under a sense of urgency in order to take advantage of being ahead and staying ahead. In a world of continuous change, urgency is another critical, yet often overlooked element of growing a sustainable business. Urgency, defined as: “the state of being urgent; an earnest and insistent necessity,” is something that every successful business should live by.

They say in life, why put off tomorrow what you can do today? When you focus that towards business, the ramifications can be very risky. Think about it, in just “one extra day” a competitor can get ahead, steal your business or get an advantage over you in a situation. In “just another week,” the competitors wind up announcing the same killer feature just a few days before you did, getting all of the press and attention. And in this day and age, “another month or two” could potentially mean the rapid rise of a disruptive competitor.

In today’s business climate, the game has changed. Operating under a sense of urgency is a vital aspect of any company who wants to win. There are too many tools available now that lower the barrier to entry and create fierce competition in almost any industry. This creates a need to stay ahead and to move fast with the tasks that will give you an edge.

Need another motivation for operating under a state of urgency? How about approaching each day of business knowing that every one of your customers is getting a call from a competitor. In many cases, this is the case. This type of thinking will help keep you on edge. Protect your house.

Does your team want to win? Once again like all aspects of business, the core of operating under a state of urgency comes down to people. Getting alignment throughout your organization that leads to a state of urgency is a lot easier said than done. Slower organizations weed themselves out naturally, the pace and approach and leadership is different. If you are ok with the status quo, or the comfortable job, then you should work for one of those types of companies. Many people though, like to be challenged and thrive to be involved in new and exciting industries. And new and exciting industries are the ones that need to operate under the most extreme urgency as they are the drivers of all innovation and change. Where do you want to be?

In an effort to clearly articulate my point, here are some of the actions you see from companies who operate under a sense of urgency:

- They provider killer customer service.

- They are continuously innovating their products and services.

- They take customer feedback seriously, act on it, and are better for it.

- They are transparent with their communications and actions.

- They actively engage with customers, prospects and the larger community.

- They are involved in philanthropic causes (the world does need to be saved, and sooner rather than later).

If you operate with some urgency you will most likely always stay in the game, operate under a sense of urgency, and you will win.

What do you think? Is a sense of urgency too extreme in your eyes or do you feel the same way? Give me your thoughts in the comments below.

Thanks for reading.