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.

As I write this, I am attending the Social Graph Symposium in Silicon Valley which I am super excited about. The event is centered around “the social graph and the implications of the social graph in business, technology, and the community.” I’ve been looking forward to it because I have been thinking a lot about social data lately, and in particular how marketers can leverage it with their communications.

Earlier this year at the Email Insiders Summit in Park City, UT, I was on a Social CRM panel with some great folks, where we were discussing in free form, the aspects of the effects of social data on customer relationship management (CRM). I wanted to expand on one of the interesting points that we only touched on in the panel, which was defining the types of social data that are available to marketers. As you can imagine, this could easily have been the focus of the entire panel. Since social data has been a focus of mine over the last few months, I wanted to put down some thoughts on how I view it’s relevance to marketers.

Social Data Defined

The idea of social data is relatively simple. With the growth of social mediums (social networks, micro-blogging, location based technologies, etc), individuals are generating out an incredible amount of activity, content and behavior on the web. This data is propagated and distributed through many channels (web, email, mobile, etc), and at the same time, a market has been evolving that aggregates this data, organizes it, and in some cases analyzes it. This type of data, albeit in some cases, data overload, can bring to bear some interesting opportunities for marketers. Lets look at the two types of social data that encompass the root of these opportunities.

Social Data Attributes

The first, is social data attributes. This is the broad aspect of defining the social graph within a given audience. Lets say for example that the audience is your customer base. Clearly, this is one of the most valuable assets to any business.

Social data attributes allow you to add specific data points to your given customer database, in particular the social graph layer. For example, maybe on average a marketer would have some basic data attributes on their customer list:

1. First & Last Name
2. Company
3. Email Address
4. etc… (the more sophisticated the marketer, the more data fields included in a customer database).

Social data attributes come into play when you can also identify where your subscribers are on the social web. What percentage of them are on Twitter, facebook, LinkedIn, etc.. ? Beyond where your customers are on the social web, there are also attributes like “influencer” data – this is where the number of “friends” or “followers” can be aggregated, and you can identify who in your customer base is a potential “influencer.” These data points can also be aggregated and appended to your database. This is the base foundation of adding the social graph layer to your customer file.

Social Data Activity

The next, and perhaps more challenging social data marketers now have at their fingertips is social activity data. What I mean by this is, what kind of conversations, interactions, posts, updates, check-in’s, etc, are your customers generating online?

This type of data, which is almost always in the public domain, truly is the “real time” heart and soul of your customer base. Aggregating, analyzing, and responding to some of this data has the potential to completely transform traditional CRM, and in many cases already has.

Just think of how much more relevant your customer interactions can be when you’ve read their latest blog post, tweet stream, viewed the flickr pix they posted from an industry event they just attended, etc. On the human level, this is social CRM. Deeper, more meaningful interactions.

From the sales & lead generation perspective, acting on social activity also helps fill the top of the sales funnel. Think about it, with the right approach, people are having more meaningful relevant conversations that start online with some kind of social activity, but are quickly brought offline for deeper discussion. I know many companies who are having great success leveraging this, mine is one of them. With these small examples, I am just scratching the surface of what is possible.

Socialize My Database

From my perspective, email and social are a beautiful marriage. When you think about where to start with all of this, your customer email database makes the most sense. Since email offers one of the most targeted, efficient and measurable mediums available to marketers today, it would make sense to build your social graph around the email address, hence why you always hear me and the folks at Blue Sky Factory touting email as “the digital glue.”

Think about it, if all of the other social mediums went away, there would still be the email address. Recent research data from Merkle’s “View from the Social Inbox 2010″ report also suggests that many people use the same email for permission-based emails as they do for social networks. This makes even more of a case to leverage your email database first.

I’ve Got the Data Now What?

Many marketers I speak with are not so much struggling with where to find this type of data, they are struggling with how to use it. This is the beginning of a new era of marketing strategy and tactics. When combined with email, some of the basic social data elements described above, the following are just some of the tactics a marketer can leverage:

1. Identify, and target influencer’s within your customer or subscriber file.
2. Create accelerated loyalty & retention campaigns.
3. Jump start a social media presence (cross pollinate your customers to your social properties).
4. Convert community into new email subscribers – build your list!
5. Build your sales pipeline by active social web participation & engagement.

Again, I am just scratching the surface of whats possible. I would love to spark some additional dialog on this topic. What are your thoughts on social data? What did I miss? Do you agree?

Feel free to comment and continue the conversation below. Thanks for reading.

I wanted to put up a quick post to mention a couple of great events I will be participating in this week. I’ll be posting my March schedule shortly as well. In the meantime, hopefully you can join me at one of the below. Looking forward to it!

February 25th – Webinar: “Email & Social Media: Community, Content & Killer Campaigns”
DJ Waldow and I will be presenting this on behalf of Awareness, Inc.

Attendees will learn:
• Why email is the digital glue of social media
• How to integrate email & social (tactical, low-hanging fruit)
• Strategies for using email & social media as complementary channels
• How to optimize content to encourage sharing
• Strategies for effective community building using email + social

You can register here.

February 26th – “Got Effective Email Marketing?” – A Panel Discussion
Hosted by ThinkBusiness Media, join me as I moderate the following panel of marketing rockstars:

Jeanne Jennings, Principal, JeanneJennings.com
Raj Khera, CEO, MailerMailer.
Jeffrey Lupisella, President and CEO, Vizual, Inc.
Bill McKay, Vice President, Direct Media Millard.

The event is in Tysons Corner, VA from 7:30-9:30. You can register here.

As Bob Dylan sang, the times they are a changing. For marketers, now the times are a changing more than ever before. Think about the landscape shift we have seen in marketing communications over the last 24 months alone. There have been incredible amounts of change and evolution in marketing mediums, and most importantly the connections, community, trust and influence that the social web has brought to the forefront.

The future is now:

Today, if you are a marketer, and you are ignoring this fundamental shift in communication, you are doing both yourself and your company a large disservice. You are putting your job on the line, and it will be just a matter of time before your organization “shifts” with or without you. As marketers it is our duty to leverage all of the tools that are available to us today.

Are you on the bus or off the bus? That is the question any savvy marketer must ask themselves these days. Sure, every market and industry is different, but everyone is going to be affected this time (they already have, many just don’t know it yet). This marketing communications landscape shift isn’t just another “tactic” to include in your media plan, this is the new frontier of marketing communications. We are in the future now.

Is your marketing department adaptable?

To me, one of the secrets to success in today’s marketing landscape is having the willingness and ability to adapt. The ability to change, hence the marketers “new normal.” What is the new normal? According to me, the “new normal” for any organization should be the ability to constantly change, with the times, the technologies, and the mediums that are literally evolving the way that we think about communicating and engaging with our customer base.

The “new normal” should always be morphing. They say, the only constant is change, and that is so true when it comes to today’s marketing landscape. As marketers, we can no longer be set in our ways. In today’s world, our ways need to be constantly changing because the optimization of our efforts is never complete. As our VP of Strategy & Innovation Chris Penn says, there is always more juice to squeeze!

Are you taking action?

Now is the time of new thinking, experimenting, evaluating and adapting. This is the time. Your company’s marketing department should be morphing into a publishing organization, and leveraging the power of your customers and subscribers networks. As I have said several times this year in my speaking, 2010 is the year of social acceleration, and TRUST and INFLUENCE in the social web will drive more purchasing decisions than EVER before.

So, as we move forward in 2010 and the landscape continues to change, it is important that we as marketers stay nimble and light. Now is not the time to “over process” your marketing function, but rather to test the waters on new mediums, learn more about your existing subscribers (social graph), build brand ambassadors and evangelists (easier said than done, yes), and most importantly LEVERAGE what is beyond your control…… the thoughts, opinions, recommendations and influence of your existing base.

Think about it.

Am I off? Tell me what you think in the comments.

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.

This coming week I will again be heading to one of my favorite places on the planet, NYC. I will be attending Ad Tech on Wed and Thur, and will also be speaking on a panel at Graham Lawlor’s Ultra Light Startup’s on Thursday November 5th at 6:30 at Sun Microsystems. The event is dubbed “Email Marketing for Startups”.

I am looking forward to it and I will be joined by some incredible folks who I can’t wait to meet. The panel looks like:

Moderator:

* Maisha Walker, President of message medium and e-commerce columnist with Inc. magazine

Panelists (alphabetic order):

* Greg Cangialosi, CEO of Blue Sky Factory
* Neil Capel, Founder and CEO of SailThru
* Lisa Klieman, Vice President, Business Development at Innovyx, Inc.
* Adam Rich, Co-founder and Editor-in-chief of Thrillist

If you are coming let me know and lets be sure to link up. If you are going to be at Ad Tech and want to link up as well drop me a line. I will be roaming the exhibition floor most of the time. See you in NYC!

This coming Tuesday at 1pm EST, I will be doing a webinar with Brian Halligan, CEO of Hubspot. Below is the overview of the session. Hope you can join us!

Get leads to come to you, then turn them into customers.  Sound too good to be true?

It’s not, and it gets even better.  No more cold calling, telemarketing, or spending tons on print and radio ads.

Enter inbound marketing.  This (more recent) style of marketing allows you to get found by potential customers online.  The key is retaining these leads, building a relationship with them, and turning them into clients.  Enter email marketing.

Join us for “Inbound & Email Marketing: So Happy Together” on Tuesday, October 13 at 1 PM ET as Brian Halligan, CEO of HubSpot, and I discuss the inbound marketing landscape and how email marketing complements this method of attracting customers.

Attendees will learn:

• Inbound vs. outbound marketing
• Strategies for using inbound marketing to attract new customers
• How to build a relationship and retain leads through email marketing
• Tips for making the most of inbound and email marketing as complementary channels

There’s only one week left to register, so sign up today!

Below, is an excerpt from the Maryland Chamber of Commerce Digital Marketing event that took place on Thursday May 14th. In this video, taken by Will Burns, I talk about how to jump start your social media community with your email database, and how to build email subscribers through social media.

I rarely do this, but somehow the stars aligned where I actually spoke to 3 entirely different groups of people, 3 days in a row about social marketing and macro level trends that are happening in the marketing communications space. The audiences were as follows:

1. Technology Council leaders of North America
2. A global provider of testing & certification centers.
3. A large law firm.

This proved to be very interesting for me, because 99.9% of the time I speak to marketers. So, taking essentially the same message and applying it to the non-profit, testing & education, and legal professions proved to be interesting, and it worked.

The one nugget that I found to be the most interesting of all was that EVERYONE GETS IT (for the most part). I started every presentation with 4 key MACRO trends, the first one being that marketers finally understand, and get the fact that we are now in a two way media landscape. The batch and blast mentality of one way media is so old school, and so foreign to the modern marketer. I feel people are starting to get this on a broader level, and they are embracing it.

Why do I feel this way? There wasn’t anyone in the room at ANY of the three talks I gave that challenged or countered some of the statements and trends that clearly outline a shifting landscape of communication for organizations and businesses. In the past someone always didn’t agree, or there was big push back on some level, once we got into the details. I actually always look forward to it, because a healthy debate / friction is always good. The closest we got on a debate was the whole personal vs. company profile, mixing the two together, or not, etc. Good one for sure.

Maybe it was just that the folks I spoke with were primed and ready to hear more. Either way, as a person who goes to a ton of events and speaks to a variety of audiences, in my mind companies are beginning to adapt. More and more marketers and organizations are applying more social marketing tactics and mediums to their outreach programs. Its not just marketers that get it either, the “organization” as a whole is starting to get it. This is good, because as many of you well know, it is happening. We are in a world of dialog marketing, so embrace it.

Would love to hear your thoughts below.

Steve Kruskamp came to Blue Sky Factory’s HQ today to interview me for his MBA class in entrepreneurship. We sat down and did a hour long interview. If you are interested in hearing about some of my experiences and thoughts around entrepreneurship check out the recording below: