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.

As CEO of a growth company, one topic that never falls off my radar is sales. Sales is the lifeblood of every company. As our COO, Doug Broujos likes to say, “if you’re not growing, you’re dying, and no one wants to work for a company that’s not moving forward.” I couldn’t agree more, and that’s the core of why sales is critical to every business.

You may have heard the old saying, “sales solves everything.” Well, I’ve come to learn over the years that it does. When your company is selling, building momentum, and closing business, then you can do things, like grow, if you so choose. That’s how Blue Sky Factory has grown, through sales. We never raised any funding to grow either, we sell and grow through revenue generation. We do that by providing stellar customer service and powerful technology solutions. We do good work, and the word spreads.

Sales is hard. It is the front lines, it’s holding down the fort, fighting off the competition, making your case, each and every day. As a founder, I know what it takes, and I also know that the only way to scale the kind of “hustle” that stems from the founder / CEO level, is to have incredible people around you representing the company, selling your solutions, over-servicing your customers, all while continuing to deepen the relationship with your customers. This practice eventually evolves into the development of a large, vast community of evangelists that not only enjoy, but take pride in, amplifying your company’s signal. There simply is no better marketing than that.

My personal approach to sales, has always been that unless I am asked directly, I don’t sell, anyone, ever. Instead, I develop relationships and nurture them and add as much value as I can when asked or when I see an opportunity. For me, this this has paid off incredibly in terms of growth, and it will always continue to be the core backbone of any business that I personally develop. It’s a great feeling when I first speak with a prospect and learn that a trusted member of my network gave my company and I a glowing endorsement. To me, that is the ultimate business development. Be there before the sale.

Scaling Sales

I’ve also learned over the years that the “Kumbaya effect” (something that will be further articulated in another post) of word of mouth and referrals, isn’t a scalable sales model. In the sense that its only one channel, a VERY important one, but unless your are looking to be a lifestyle business, it can’t be the only one. A growth company should have many channels working towards attracting people to their sales pipeline.

As an organization grows, it becomes critically important for marketing to fill the top of the funnel with prospects, ideally qualified ones. It is then up to the sales team to engage with those folks, identify real opportunities, and bring in the customers. Sometimes, and more often than not, in order to achieve your goals you need to be aggressive on the sales front. This clearly speaks directly to the team you have in place. From what I have seen at my company and others, successful sales people have a lot going on, all of the time. This is no 40 hour work week if you want to win.

What can seem like a potentially overwhelming schedule, ie. a high volume of people to connect and follow up with, managing multiple opportunities at various stages, writing proposals, having meetings, traveling in some cases, etc., is really the regular schedule of a successful sales person. In fact, a successful sales person wouldn’t have it any other way. They thrive off of this type of schedule and activity, and they love building momentum. That said, the most important activity of a successful sales rep is their ability to manage all of that, while continuing to build the top of their funnel.

Building the Funnel

While marketing may fill the top of the funnel, its the job of sales to build their own pipeline of prospects and opportunities – ideally from both inbound and outbound channels, (though I know many organizations differ on their philosophy of inside / outside sales, etc). The importance of this is critical to building momentum and to ensure that once you have a good quarter, a good month, a good week, or a good day, that more good ones follow. This is key to a continuous flow of success. All to often though I hear about sales people who peak and valley with success all year long because the front end of the funnel never has enough time and energy put towards it. In order to win, you need a large pipeline of opportunity at every deal stage.

The Bottom Line

At the end of the day, the reality is, in the words of Alec Baldwin, coffee really is for closers. I’m not going to sugar coat it. Sales is hard. It takes tenacity, resilience, and a passion and motivation to succeed. If you are in sales and you don’t have these things, you will never be as successful as you can be. If your sales team lacks those traits, then you might want to take a hard look at whats going on.

Sales is a very large subject, and I realize I haven’t deep dived into everything, and there are many factors involved in successful sales, but there are some fundamentals that I have come to learn over the years.

To recap, here are 10 fundamental elements of sales:

1. Sales is critical to every organization and must be treated as such.

2. Having a great product & service helps the sale every time, but that’s not enough.

3. People buy from people (and brands) they trust. Be one of those people & brands.

4. While word of mouth and referrals are great. Never rely purely on the good will of your network.

5. Everyone in sales should strive to “be there before the sale” as often as possible.

6. Marketing fills the funnel, sales BUILDS their own funnel from that (individually).

7. Sales must never neglect the top of their funnel. This is the seed for all future success.

8. Sales is hard. It takes time, patience, resilience and dedication. You can’t be on and off from one day to the next.

9. Sales success doesn’t come in 40 hour work weeks (Though I have seen it done in much less than 40, but that’s Ninja status )

10. Sales isn’t for everyone. Coffee really is for closers.

These are just some of my thoughts. Whats your take? Am I wrong? Want to add your own flavor to this? Let me know your thoughts below.

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.

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 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!

I am really excited about Bootstrap Maryland. When Jared Goralnick first asked me to be a part of it I hadn’t even realized he had been working on such an interesting and important event. I’ve always thought an event that brought together similar entrepreneurs who have experience building businesses outside of the most common routes, (ie. raise friend and family money, raise angel investment, raise VC, etc) would be extremely valuable to the next generation of entrepreneurs. Our region is ripe with talent, ideas, and products that are already in “the lab” and just waiting to officially “launch.”

I look forward to sharing my story and advice around building businesses with little to no funding at all. It certainly isn’t easy, but it can be done with, as Jared states “drive, brains and little creativity.” Details on the event are below, or you can click here. If you are thinking of starting a company, or already are out of the gate and are looking for some additional inspiration. Hope to see you there on May 2nd.

Bootstrap Maryland brings together young entrepreneurs and the necessary tools for running a lean and successful technology business.

At the Bootstrap Maryland Conference on May 2, 2009 you will learn how to turn your web or technology idea into a business. The presentations will cover topics such as:

* What you need (and don’t need) to get your business off the ground.
* Most products fail due to lack of marketing, not failed technology. How to get the word out inexpensively with social media, events, and creative PR
* The most relevant technologies people are using today, and ways to get the technology right the first time
* Stories, lessons learned, and discussions from young people who have built successful businesses

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.

I can’t stress how much respect I have for Tony Hseih. I had the pleasure of watching him give the opening keynote at SXSW last week. His message is very powerful. Zappos “gets it.” Video highlights of the keynote and his slides are below. Enjoy:

Click here to view the embedded video.

Click here to view the embedded video.

Zappos – SXSW – 3-14-09

View more presentations from zappos.