The 50 Personal & Business Lessons I Learned in 2008

At the end of each year I post the business and personal lessons I learned that year. You can see the 2007 lessons here, the 2006 lessons here, and the 2005 Lessons here. Here are the 50 Personal and Business Lessons I learned in 2008.

The 25 Personal Lessons I Learned in 2008

1. Don’t Cheat on Your Wife. Don’t cheat on your wife, period. But especially don’t cheat on your wife if you’re planning to run for national office. I learned this lesson from John Edwards in August.
2. Don’t Hire a Prostitute. Don’t hire a prostitute, period. But especially don’t hire a prostitute if you’re already well-recognized and a Governor of a major U.S. state. Thank you Elliot Spitzer.
3. (Some) Women Can Get Very Jealous of Other Women - I am very careful not to over-generalize here. In my experience, some women can get very jealous of other women, especially those that you previously dated, even if there is no real reason for them to be. If you’re in a relationship with a woman that you care about, make every effort to make her feel like she is the only one. Make sure she understands she is the person you want to be with.
4. Women Have Amazing Natural Instincts. Remember when you were a kid and you thought you were getting away with something but your mom knew all along. I thought I had hid the bottle of Bacardi 151 safely in my closet and then one day it was gone without explanation. Yes, women have amazing instincts and will generally catch you at anything you get yourself up to. Be open, honest, up front, and transparent with them.
5. Don’t Fall For A Woman Until You Know Her Well. Don’t fall for what you think women are or who they are on paper, but rather who they actually are, whether they like you back, and how well you can communicate. I’ve made mistakes in this area a few times in the last two years–falling for women based on who I thought they were (or who I wanted them to be) rather than who they actually were, whether they liked me as well, or how we communicated.
6. Life Can End At Any Time. Live Fully And Don’t Wait to Make a Difference. On March 5, 2008 UNC Student Body President Eve Carson was killed in Chapel Hill by multiple gunshots to the head after being kidnapped from her home. I knew Eve when she was Co-Chair of Nourish International. I wrote this post at the time. The words of her father, Bob Carson, at her memorial service on March 9th will forever live with me…
   

   “I see a stunningly beautiful convergence of talent and caring in this, our children’s, generation. I believe that these kids, along with their peers around the globe, can reach reasoned solutions for mitigating violence and tacking many of the inequities of poverty, prejudice, inadequate healthcare, and under-education. This is no pie-in-the-sky-wish! These kids are smart. They’re so capable. They’re more productive because they collaborate and communicate like no generation before them… But I must tell you–even with an aching heart, and yet with such hope and love–that the friends of Eve, and their generation, will not be denied. They’ve got miles to go and missions to keep.”

7. Humor has great power. Jeff Dunham is absolutely hilarious. Achmed the dead terrorist is perhaps the funniest politically incorrect puppet in the history of puppets. “Silence! I kill you!”
8. When You’re Speaking to Middle Schoolers, Use Audience Interaction. In February I talked to 200 middle schoolers at Moore Museum Middle School in Raleigh. It was my first time talking to that age of audience. I learned a few key lessons regardless of your age. Don’t go more than 5 minutes without asking the audience some form of interactive question. Use vocabulary that is at their level. Do cool dances. Do not show vulnerability. Get your message tight and repeat it.
9. It’s Hard to Beat Oprah. On February 5th my book Zero to One Million launched from McGraw-Hill. It reached #2 on Amazon and made the Wall St. Journal Bestseller List after an aggressive launch through social media and friends of mine with large email newsletters. We reached 4 million people and sold about 4,500 copies that day via Amazon, more than the 2,500 books one has to sell on a normal day to reach #1. We would have reached #1 had it not been for Oprah promoting Eckhart Tolle’s new book A New Earth on her show that day causing it to sell 7,500 copies in a day.
10. You’ll Get Sick If You Sleep in the Cold. In January, after speaking at Fairmont State University in West Virginia, I slept in the Extreme Entrepreneurship Tour RV in a parking lot instead of getting an extra room at the hotel we were at. It was about 70 when I went to sleep at 1am but about 40 when I woke up at 9am. I didn’t know that the generator (and thus the heat) had been left off. I was sick for the next week. I learned that when you sleep in a place that gets below 50 degrees, you will more often than not get a cold as your body doesn’t have the heat to kill germs and infections.
11. Arrogance is Being Dismissive of Others Not Overconfidence. Growing up, I thought the definition of arrogance was having too much confidence. This was difficult for me to understand as I’ve always been an extremely confident person and knew that over-confidence was absolutely essential to any chance I had at succeeding at a young age. After a number of good conversations with my former girlfriend Erin I was able to learn the lesson that arrogance is not over-confidence, it’s being dismissive of others and not showing care toward them.
12. In Berlin, People Go Out Every Night of the Week. I was in Berlin in May with the Transatlantic 2020 program. The young people in Berlin tend to go out every night of the week including strange nights like Sunday, Monday, Tuesday, and Wednesday. I went to a Techno Club called Tresor in Berlin on a Tuesday night and it was absolutely packed.
13. In Dubai, You Can’t Get In a Nightclub Unless You Have a Woman With You. I was in Dubai for a night in July with my roommate Roey Rosenblith. We were on a stopover on our way to Uganda for a week. It was a Saturday night. We went out expecting to see the tales of the crazy Dubai we had read about in Rigged. The reality,  two 23 and 26 year old Americans could not get into a nightclub in Dubai without a woman with us unless we bribed the bouncer with $30 each which we refused to do on principle. We should have found a woman to say she was with us.
14. In Uganda, The Driving is Insane. I’m not talking mildly insane or moderately crazy. I’m talking absolutely off-the-heezy psychotic. I remember riding in the passenger side of a van driving on a two-lane dirt road while our driving proceeded to pass a car that was already passing another truck, causing us to end up in the dusty shoulder of the other side of the road while a truck carrying about 35 people standing it its back rambled toward us.
15. There Are Tremendous Investment Opportunities in Africa. In Uganda there were so many business opportunities. Incorporating a business (which Roey did while there) took only 3 days versus 3 weeks in the U.S. There were 20 story skyscrapers, lawyers, and banks. Africa is by no means represented fully by the pictures of suffering children we so often see (which is also real). Much progress can be made in reducing poverty through socially responsible investing and entrepreneurship.
16. Seek to Understand The Other’s Perspective. One of the most valuable things I learned from Vanessa while dating her this year was how she was able to be so compassionate and universally loved. This seems so obvious in hindsight. I learned that she always first looked at things from the point of view of the other person.
17. Don’t Forget To Be Your Age from Time to Time. One of the lessons I’ve learned most from my friends James Forsyth and John Hinson this year is to open up, be real, and take life less seriously. To act my age from time to time rather than acting 40 all the time. Since taking this lesson to heart, I often can be seen dancing to Flo Rida, swimming on the floor of my office with deer or talking to my stuffed animals on a love seat :-). There may not be many CEOs who would do this, but wouldn’t the world be more enjoyable if they did?
18. It Takes 10 Years To Become Great at Anything. Here’s a key learning from Malcolm Gladwell. It takes about 10,000 hours (10 years at 4 hours per day) to become Great at anything. You can only become Great at 6 or 7 things in your life. Choose carefully.
19. Don’t Leave Your Blackberry in Your Pocket When You’re Making a Speech. Even if you’re phone is on silent, your phone will cause the microphone to go nuts when it rings due to interference.
20. If You Drop Your Blackberry in the Toilet, Get it Out Quickly and Remove the Battery. I did this in October at a EO retreat at Lake Gaston. I removed it quickly, dried it upside down, but was unable to save it from certain death. I later learned had I removed the battery right away and let the battery dry separately it would have had a chance due.
21. There Is A Lot of Crap in the World. Genocide, war, people getting hung, shot, run over, earthquakes, vitriol, people who don’t believe in you, murder, rape. Sometimes it’s difficult to cut through it all and believe that anything is possible. And yet, a driven, caring, passionate individual can make a huge positive difference.
22. The Value of a Human Life is Equal, But Most People Don’t Agree With Me. When you see Cyclone Nargis kill 146,000 people in May in Myanmar and an earthquake kill 69,000 in the Sichuan province of China just two weeks later and so few people talk about it or even remember eight months later, it definitely takes a toll on my human spirit. For some reason the value of lives is seen as different based on which nation-state someone is from. When 200 Americans are killed it’s the biggest story for three months. When 100,000 Asians are killed no one remembers 90 days later. What the f? To me a human is a human regardless of where he or she was born or is currently located. I wish our media agreed.
23. Photography Has Great Power. Just look at this collection of 2008 in Photographs (part 2, part 3).
24. It is Better to Love and to Lose Than to Never Love at All. In other words, it is better to live life to its fullest, even if one day you may forget it. The key message of Eternal Sunshine of the Spotless Mind.
25. I Love New York. I was sitting at a Starbucks in Murray Hill (around 30th St and Lexington on the lower east side) over the Memorial Day weekend in May. I love the architecture, the culture, the art, the diversity of people, and the drive of the young people that live there. It’s the commerce capital of the world and you can go hip hop dancing every night of the week. While long term I want to end up in beautiful North Carolina, I do look forward to living in Boston and then NYC at some point in the next ten years. I wrote in my journal while at that Starbucks.
    

    “There are just cute, smart, driven, ambitious 24 year old women fricken everywhere. Especially love the Murray Hill area of town where I’ve been staying with Ryan Alovis. The parks are great. Walk back from Union Square was great last night. And all the investment bankers and private equity managers are here too. You can get anything you want anytime you want. Seriously, 2 more attractive mid-20 year olds just walked by. And another. And all wearing spring dresses. So much great diversity. Columbia was beautiful yesterday. So much activity and action. OMG another one. They are all over the place. People smiling, living. Restaurants, bars, parks, dancing, expression, tall buildings, public transport, sports teams, big concerts, being able to be yourself.”

The 25 Business Lessons I Learned in 2008

1. Business Conditions Can Change Quickly. There was a Sunday night in September that changed everything in the financial world. In one day, Lehman Brothers had filed for bankruptcy and Merrill Lynch had agreed to be acquired by Bank of America. Still to come was the AIG bailout, Morgan Stanley and Goldman Sachs’ conversion into bank holding companies, and the sale of Wachovia to Wells-Fargo. In our world of Software-As-a-Service (SaaS), average valuation multiples dropped from 3.5x to 2x forward year revenues in just 45 days.
2. There Are Parts of the Stock Market I Don’t Yet Fully Understand. Although I’ve been an entrepreneur since age 11, majored in economics, and read everything I can get my hands on about finance I’ve still got a LOT to learn about markets. On September 16th, I thought that the Fed bailout of AIG would stabilize markets and that the DJIA had seen its low at 10,742. Sixty-four days later the Dow closed at a low of 7,552, another 29.7% drop. I’ve still got a lot to learn about the TED spread, credit default swaps, counterparty risk, collateralized debt obligations, liqudity, and the effect of rapid de-leveraging.
3. There Are Parts of the Commodities Market I Don’t Yet Fully Understand. I also thought that the per barrel price of oil had seen it’s low at $88 in September after dropping from $147 in July. As of December 27, the price of a barrel of crude on NYMEX is $37.71. You’d think that the price of such a fundamental commodity to world growth couldn’t possibly drop 74.6% in six months–but you’d be wrong. Ahh, hedge funds, speculation, and perceptions of demand.
4. Don’t Fret About Decisions That Aren’t Yet On The Table. In August I found myself spending hours and hours considering and debating whether iContact should raise another round of venture capital or not. We had six firms interested, all at nice valuations and at favorable terms. It was just a matter of 30 days or so until we got term sheets. I spent four hours one evening while at a Pacific Crest conference in August writing an 8 page analysis of the pros and cons. By the end of September, the market had changed dramatically and all the consideration was irrelevent. I spent a few too many hours considering what we would do in a scenario that wasn’t yet on the table. We ended up choosing not to raise equity capital and went with a venture debt round from North Atlantic.
5. If You Raise Venture Capital, the Required Sale Price of Your Firm Goes Up to Have Equal Success. I learned this lesson in 2007 when we raised our first round from Updata Partners. At that point, we could have had a very successful exit for iContact at any reasonable sale price (since we received our shares at par value of $0.001 each). Once we raised funds at a $30M post-money valuation, suddenly we had to have an exit north of $60M to be seen to have had a success (and $90M for a true success) in the eyes of our investors. This ‘re-setting of the bar’ phenomenon due to a new investor coming in at a higher per share basis price is key for entrepreneurs to consider when deciding whether or not to bring on outside capital.
6. Viral Video Can Be A Powerful Form of Communication. Our iContact iNews videos have been powerful for building and sharing our culture. The Yes We Can video got over 14 million views and made an important impact in the primary election vs. Hillary Clinton. It was released just three days prior to Super Tuesday February 5th. Virtualization server company VMware hosted a viral video contest called “Virtually Famous” in May. They basically got all their users/fans to produce a catchy advertisement for them. Then they had their fans’ colleagues and friends  vote on the best one–which drew tens of thousands of new viewers to watch an ad for their company. My friends from Cary won with their production “Hardware Hotel.”
7. Focus. Something I’ve learned to be critically important is focus. Once I figure out what I want to achieve I go after it until it has been achieved. Right now and for the next few years of my life my focus is building iContact into the leading provider of email marketing services for SMBs and non-profits. Nothing will stop us.
8. Let People Know What You Are Doing And Why. Have conversations with your key people to let them know what you are doing and why. Even if it’s absolutely clear to you why your top 5 business priorities are your top 5 business priorities, that does not mean your direct reports understand why you are working on what you are working on. Have frequent conversations with your team about the company’s top five priorities and your top five current priorities. I choose to list them monthly in a powerpoint package we review as a team.
9. Get Input in the Planning Process. Even if you have the best plan in the world it won’t matter if it doesn’t get executed well. And it won’t get executed well if people aren’t bought into it. They simply cannot buy into it unless they understand the reasons for it and have a role in providing input and structure.
10. What you Measure, Gets Managed. If you measure, set a target for, and compensate on a KPI (key performance indicator) like phone abandonment rates, your phone abandonment rates will suddenly improve. We started measuring phone abandonment rates (the % of your customers who hang up while on hold before you can answer the phone) in July of this year and within 6 weeks the percentage of abandoned calls went from 9% to 4%.
11. Human Psychology Responds Well to Deadlines. There is great, great power in using deadlines, especially as it relates to sales. Our previous record for new customers in a day was 106. On March 31 this year, during an end-of-quarter sale, we added over 225 new customers during the day. Of course, there was an added incentive that day…
12. When You Want a Team to Reach a Stretch-Goal, Say You’ll Shave Your Head. It was March 9th, we were on track for about $930,000 in sales for the month. I told our team at a company lunch if we hit $1 million in sales that month, I’d shave my head. We hit $1,030,000 and there went my hair.
13. Let Your Customers Play a Big Role in Product Management. When you’re ready to improve your product or add additional products, don’t add what you think your customers want, add what they actually want. Ask your customers informally via focus groups and formally via an online survey. Ask them what their needs are and what additional features or products that they would receive value from. Also keep in mind that sometimes having too many features can decrease ease of use of your product and thus lower conversions. The book The Breakthrough Company has a good saying–”As you diversify, let your customers lead you.” The book Ready, Fire, Aim says (and I’m paraphrasing here), “Let your customers determine your development order and timeline by a vote.”
14. My Ideas Matter Less Now. When we had 4 or 8 employees, my ideas were important. Today, at 150 employees my ideas matter much less than those of the team we’ve put together. What’s important is that we’ve hired the right people, put the right systems and processes into place, and empowered them to think and execute. Today, my time isn’t spent writing Product Requirement Documents or Marketing Plans, but rather ensuring our team has what they need (capital, people, systems, metrics) to get their jobs done. Today our focus is to build our team up into leaders, thinkers, and innovators.
15. Everything is Negotiable. At iContact, we have one of the best CFOs in the technology business period, Tim Oakley. He is a tough negotiator. I’ve learned from Tim that everything is negotiable. There is no such thing as “reality” as every single person has a different perception of reality. Therefore, one can guide and structure reality. Reality is negotiable.
16. M&A Firms Position Exit Value Using Synergy Value, Scarcity Value, and Strategic Value. We hired an investment banker to assist us in raising our round of investment this year. As part of this process, we learned a lot about mergers and acquisitions of companies, which they also represent companies for. Investment bankers will work to position a company at a premium to the valuation of comparable companies by assessing synergy value (the value of the added cash flow created by selling the products and services of the acquired company to the customer base of the acquirer), scarcity value (the added value if there are few substitute companies that an acquirer could purchase instead of you) and strategic value (the added value to the acquirer of your brand, competitive position, team, processes, culture, technology, and intellectual property that will help them create added cashflow within their own business).
17. Restate The Other Person’s Point Before You Begin. A lot of managers are poor listeners. Two years ago in improv classes I learned the “Yes And” principle. The same principle can be applied to either external negotiations or internal debates to help people feel heard and valued. It can be extremely helpful when in a discussion or debate to purposely restate the other person’s point and then add on to it. Try starting with “Yes, I see that such and such and…” instead of the too common, “But.” The formula is [RESTATE THEIR POINT]… and…[MY POINT OR COUNTER-POINT].
18. Market Valuation is Determined By One Willing Buyer and Seller. The valuation of any company is determined by a number of factors. All valuation models eventually come down to the present value of future net profits. The challenge is in figuring out what you actually think those future net profits will actually be and then which discount rate to use. But the bottom line is that valuation is simple–it’s the price a willing buyer and a willing seller agree upon.
19. All Disappointment in Life is Caused By Misaligned Expectations. This phrase is the perhaps the favorite saying of Tim our CFO after ‘net-net’ and ‘the sale is different from the install.’ It means that unhappiness in business and in life is caused when reality turns out different than expected. The human mind needs time to adjust, plan, project, and set expectations. For example, if you know that you are going to have to send a team member to Las Vegas for three months for a project (which could be exciting or disappointing depending on the team member), tell them as soon as you know not a couple days before they have to go. By telling them right away they will have time to adjust, plan, project, and set expectations and will be much more likely to enjoy the experience and be productive. I didn’t understand this when I was younger, but people require time to adapt to upcoming change.
20. Always Be Testing. If you or your company is not using at least 15% of your marketing budget to test new marketing channels each month, something is wrong. One should always be testing new customer acquisition channels. And don’t say you’ve tried them all or there aren’t enough to test. Have you tested local radio, network radio, satellite radio, classified ads, magazine ads, trade journal ads, newspaper ads, newspaper inserts, flyers, vertical-targeted direct mail, market-targeted direct mail, direct mail inserts, local television, cable television, DRTV, skywriting, phonebooks, airport ads, online co-registration, offline co-registration, affiliate programs, CPA deals, call centers, tradeshow sponsorships, search engine optimization, paid search, and banner ads? If not, get to work!
21. Don’t Make Too Few Mistakes. The corollary to testing with 15% of your budget is to be willing to make mistakes and learn from them. In business and in life you learn when you make mistakes. Mistakes are how you grow and scale. Make sure you are failing at a high enough pace in order to succeed.
22. Enable an Environment of Trust. As a Director Team we read Patrick Lencioni’sThe Five Dysfunctions of a Team at our annual Director Retreat in Virginia this year. Here’s an overview of The Five Dysfunctions. One of the key principles of the book is to work actively to get your management team to understand each other and where each person comes from. The first exercise we did at the retreat was to share our ‘personal histories’ with one another. We shared basic information like where we were from, siblings, first job, worst job, why you came to iContact, and life goals. It was amazing what we learned from people we had been working with for years.
23. Have Some Conservatism in Your Annual Plan. Most companies once they leave the start-up phase develop what’s called an annual plan. In it, you project your bookings, revenues, expenses, net profits, and cash flows by month usually about 3-4 years into the future, with particular focus on the current and upcoming calendar year. It’s basically a budget with variable drivers (in our case acquisition, churn, and average revenue per user). At iContact, we have an Annual Plan that is reviewed and approved each December by the Board. Once you raise venture capital, you are judged as a CEO primarily by whether you hit or miss your projections. Many CEOs make the mistake of making their projections unreasonably high in order to get a higher valuation which then causes the venture firm to put significant pressure on the CEO to hit these projections which just cannot be done. At iContact, we’ve always had aggressive projections (120% annual growth is always aggressive). But we’ve always been careful not to provide a Plan we didn’t think we could actually hit. I prefer to have plans that I’m 50% sure we’ll hit (expected case plans). Our CFO prefers plans that he’s 75% sure we’ll hit. He’s usually right.
24. Know Your Net Lifetime Value. Quick–what is the value of an average customer to your business? Don’t know? Ha–what type of entrepreneur are you? Seriously, come on. You better know this. To calculate it, take the average purchase price x the number of times a customer will order from you (over the average length of time they’ll be a customer). This will be your lifetime value (LTV). Then multiply your LTV by your gross profit margin % (Revenues minus Cost of Goods Sold) to get your Gross Lifetime Value (GLV). This is the very maximum amount you can spend in advertising costs to acquire a marginal customer and still breakeven in the long run. Then multiply your LTV by your net profit margin % (Revenues minus all expenses) to get your Net Lifetime Value (NLV). This is how much profit an average customer will be worth to your business.
25. Never Ever Undersell Yourself. When I got started with iContact back in 2002 I was 18. I dreamed what I thought then was a big dream. We would build a company to $1 million in sales. Beyond that mark, I didn’t envision. When we reached the $1 million mark in September 2005, we had to re-plan and re-decide what we wanted to go after. When we began, I didn’t think it was possible that we would build a company to 150 employees and $20 million in annualized sales. I certainly didn’t think that we’d have a shot at building a company to 1000 employees with a billion dollar market cap. When I went out to raise venture capital the first time in November 2005, I undersold the company and undersold myself. My goal wasn’t BIG enough HAIRY enough or AUDACIOUS enough. I knew deep down in my soul we’d get there but didn’t know HOW. Because I didn’t yet know exactly HOW I didn’t share what I knew we were going to make happen. We didn’t get a term sheet from a number of VC firms then because I undersold what I knew we were going to make happen. I’m not advocating overselling either–just selling appropriately based on what you know if your heart of hearts you’re going to make happen. I’ll never undersell myself again. As my friend Elliot Bisnow likes to do, “Sell it big and then make it happen.”

I’m off to Charleston for a Renaissance Weekend. I hope you’ve enjoyed these lessons! Comments are very welcome!

2008 By The Numbers

The next few days I’m going to be writing some posts reviewing this past year. Here’s the annual ‘by the numbers’ post. You can view 2007’s By the Numbers post here. I do these posts to understand trends in life. Since every thing I do ends up on my calendar, I mainly use the search function in Outlook or Zimbra to find most of these numbers.

I’ve been very fortunate to travel widely and do all these things at a young age and I do not take it for granted. I count my blessings every day to be able to go into work where the people are like a family and to be able to see the world while growing a business. I’m especially fortunate to be in an industry segment that is growing rapidly while so many others are not.

In terms of communication, well, I’ve been a hypercommunicator for some time now. In 2008, I received 41,224 emails, sent 15,036 emails via a computer, sent 2,251 emails via Blackberry, received 5,140 text messages, sent 4,320 text messages, received 1,170 Facebook messages, and sent 340 Facebook messages. I averaged receiving 130 and sending 60 electronic communications per day during the year. My Blackberry, Outlook, Zimbra, and Facebook have been invaluable and essential tools.

This year was especially crazy for travel with the book launch in February and raising a round of funding in the Fall. I ended up visiting 36 cities, 27 States and 6 countries including the U.S., Mexico, Uganda, Ethiopia, the UAE, and Germany. I flew on 74 different airplanes and spoke in front of about 8,475 people at 37 different speaking events. I visited New York City the most at 7 times and Chicago, D.C., and Charlotte 5 times each.

I “never ate alone” for lunch and seemed to be at Doce in Meridian Parkway every workday I wasn’t traveling. I had 123 business lunches (106 of which were at Doce), I went to 27 business dinners, I went to 14 non-profit board meetings for CED, Leadership Triangle, EO, and Nourish International, I hosted 13 Entrepreneur & Social Entrepreneur Meetups at my house in Chapel Hill with about 60 attendees each, and I attended 5 non-profit fundraisers and 4 political fundraisers. In the social media world, I got up to 2,556 connections on LinkedIn, 163 followers on Twitter, and 2,043 friends on Facebook (only confirming people that I’ve actually met).

At iContact, we have had a tremendous year. We started the year with 73 team members and ended the year with 150. We added 22,000 net new customers. We had 86 million pageviews, 9.5 million visits, and 4.4 million unique visitors come to iContact.com. Our customers sent a total of 2.8 billion permission-based emails to their customers and subscribers. We monitored 84 KPIs at work. We spoke with 22 venture capital firms regarding investing in iContact in 2008 and received 4 term sheets (and accepted a round of venture debt from North Atlantic). iContact won 4 awards this year including CED Growth Company of the Year, TBJ Best Places to Work, INC 500 #85, and Ernst & Young Carolinas’ Entrepreneurs of the Year. iContact contributed over $55,000 to to 39 non-profit organizations as part of its charitable giving program in 2008.

I kept writing and publishing as always. I wrote 67 blog posts on email marketing at StartupNation.com and 57 blog posts here on Ryanallis.com. I published 4 new videos to YouTube and James Wong from iContact has posted 7 other videos of the monthly iContact iNews. In the press world, I was on CNBC’s The Big Idea in May for the second time and on 14 radio shows as part of the February book tour.

In my personal life I saw 24 movies, read 17 books, went to 10 different dance clubs, dated 9 women (only 1 seriously), went to Frankie’s Fun Park to race go-karts 5 times, played 5 games of flag football and ultimate frisbee, hosted 4 parties, and added 3 roommates to our house of entrepreneurs and social entrepreneurs in Chapel Hill.

It’s been an amazing year and I look forward to 2009!

Movies seen: Eternal Sunshine of the Spotless Mind, Blood Diamond, Juno, Definitely Maybe, Pursuit of Happyness, Death at a Funeral, 300, The Last King of Scotland, Step Up, Step Up 2 The Streets, Honey, You Got Served, Unlocking Africa, W, Bolt 3D, Why We Fight, Battleground, Wanted, Gremlins, Quantum of Solace, 21, Made of Honor, Jeff Dunham’s Christmas Special, Frost/Nixon

Books read:
Losing My Virginity, Valley Boy, Confessions of An Economic Hitman, The Difference Between God & Larry Ellison, Ready Fire Aim, Buffett: Making of An American Capitalist, The Four Hour Workweek, Audacity of Hope, Dreams From My Father, The Five Dysfunctions of a Team, Ahead of the Curve, Rigged, Ugly Americans, Warren Buffett Financial Statement Analysis, Long Walk to Freedom, The Dream, Peace is Every Step

The 40 Business & Personal Lessons I Learned in 2007

Personal Lessons

1. Life is precious and can be very short. Value it, keep things in perspective, and count your blessings. In February, I was driving down I-95 in Maryland in a snow storm on a Sunday evening trying to get back home to North Carolina when my car spun out after accelerating out of a toll booth area. I did a 180 degree spin, hit the front of another car, then continued another 180 degrees until I was straight again. My engine had cut off and I was drifting at 3-4 mph towards the curb when I realized a semi-truck was coming at my car. It missed me by about five feet. I really wanted to get back home that night so I could be at work the next morning but realized very quickly that it wasn’t worth trying. I sometimes can get wrapped up in what is next, what objective I am I pursuing now, and what appointments I have coming up. I realized it wasn’t really a big deal at all if I was stuck in Maryland for the night while the storm passed and missed a few things at work the next morning. I’ve also learned metaphorically not to accelerate in the snow without tread on your tires–you might spin out.
2. One can see much further if he stands on the shoulders of giants. I’ve been fortunate to develop a few great mentor relationships over the past year and added a few tremendous people to iContact’s Advisory Panel like Jud Bowman, Merrill Mason, Mike Doernberg, Mike Fitzgerald, and Buck Rizvi. I met Brett Icahn, Bill Clinton, and Marc Benioff during 2007 and learned from their wisdom.
3. It’s hard to stay in the game for very long when you’re not happy. Consistent hard and intelligent effort over multiple years is a key part of what makes a start-up succeed. It can be hard to sustain consistent effort for five, six, seven, or eight years. I’ve found that taking the time needed to make sure you are happy in what you are doing is an important investment. If you do not take this time you will generally not be able to last long. While I worked harder than ever before in 2007 (except perhaps in 2003 our first year), I’ve made sure I’ve taken time to build personal relationships, create memories, be with family, hold Entrepreneur and Social Entrepreneur meetups, read about the world, and speak to aspiring entrepreneurs–things that keep me happy and productive. I’ve found that I cannot help others if I am not happy and healthy.
4. I am an extrovert–I feed off the energy from others. I love to meet with and interact with passionate, driven people. I took a few MBTI-type tests in 2007 and in each one I was very much an extrovert. I refresh and get my energy by being around people. I do enjoy being alone in multiple-hour blocks in order to get work done, but as soon as the work is done I want to be around people again.
5. We are all humans and should stop killing each other. I find it difficult to understand why human genocide and warfare still happen in an age of easy communication. I will spend much of the rest of my life working to create stronger societies and reduce human suffering and end extreme poverty and war while creating access to education, healthcare, technology, and food. I became more committed to this life mission in the past year. There is absolutely no good reason in our world of opulence and riches that 26,000 children should die every day from preventable diseases and starvation in the developing world. We should have a global identity and stop create false separations and divisions.
6. The world has more opportunities than you might think. Sitting in a room planning to start iContact in 2003, Aaron and I could not and did not fathom we’d be able to create an 80 person company with a $10 million run-rate by the end of 2007. It was beyond my imagination. I am a very confident and goal-oriented person but could not even see beyond getting 2500 customers. We now have 18,000. Opportunities and possibilities will open up that today you cannot even think of today–if you just take the leap of faith and get started and keep at it. The opportunities get bigger and more interesting as your grow. If you are in business, you learn about raising financing, strategic acquisitions, convertible debt, private placements, private equity, and leveraged buyouts. As you add experienced people to your team that understand and have completed sophisticated transactions, many opportunities open up to you. The world of institutional capital is absolutely fascinating–and yet is almost off limits unless you bring someone onto your team that understands it or are able to build your company beyond a few million dollars in sales. At that point, they start calling you.
7. Keep associating with extraordinary people. I have been greatly helped by the relationships I’ve been able to make with people in New York, Boston, D.C., Chicago, Los Angeles, and San Francisco. For understandable reasons–I’ve found that large groupings of young, ambitious, extremely smart, passionate, dedicated people tend to live in major cities. I love North Carolina and hope to spend the majority of my life in the State. But there is no doubt at the moment that there is a brain drain of the best and the brightest to New York, Boston, D.C., and Atlanta after they graduate from UNC, Duke, and N.C. State. I started the Entrepreneur & Social Entrepreneur Meetups in June as one way to get smart passionate driven people who care about changing the world to associate with others who are similar and encourage them to stay in North Carolina after they graduate. The meetups have grown from 8 attendees at the Wine Bar in Chapel Hill in June to 60 attendees at my house of social entrepreneurs in Chapel Hill today. I’ve found that tremendously positive developments can occur when you connect smart people and when you choose to associate with extraordinary individuals.
8. Don’t write off dating women of any type. While in New York with a group of friends in February, I wrote off dating women who were older than I due to many of them wanting to get married right away. As soon as I did this, I met a wonderful 25 year old woman in New York who I learned a lot from and then began dating a 28 year old woman from North Carolina who I also learned a lot from. I was wrong to write off women who are older than I. I learned I could often relate better to women who were in the professional world already doing something to change the world versus in school. At a point during the Summer, seemingly not having learned the full lesson yet, I wrote off dating younger women due to not being able to relate professionally and often intellectually with them. At one point I decided to stop trying to actively date women seriously at all until I was older and could actually meet someone younger than I was who was making serious efforts to change the world and reduce human suffering. As you can predict, I of course was proven wrong again. The lesson I learned is that while I can develop helpful guidelines that are often true in regards to dating, I should not categorically write off women of any type. I found the chances just as high to meet a brilliant driven ambitious 20 year old as they were to meet a professional 27 year old who could care less about getting married right away.
9. Humans have a deep desire to be accepted for who they are and not judged. Being judged personally can have positive consequences such as getting helpful feedback or getting life guidance, but it can often hurt. I’ve yet to truly figure out and reconcile when it is a positive experience to judge another human and when it is best to simply accept them as they are. Perhaps the separating line may be in business versus outside of business. In business, judgment and guidance based on facts and metrics can be very helpful. Outside of business, I’ve seen that humans often want to be loved and accepted and not judged–at least before they are truly known by an individual. I admit I’m a bit confused still on this lesson, but I’ve learned it to be true in many cases personally nonetheless.
10. Gratitude is an extremely powerful character attribute. I watched the movie The Secret three times in 2007. While it has some seen some deserved criticism for being ‘over the top’ a bit, it nonetheless is one of my favorite movies of all time if not my favorite. The principles it shares are the exact principles I’ve used for the past six years and are the same principles found in Think and Grow Rich, one of the thirteen books that have changed my life since I was 17 (the others are Rich Dad Poor Dad, Rich Dad’s Guide to Investing, The Lexus and The Olive Tree, The Commanding Heights, The Spirit of Enterprise, The Worldly Philosophers, The End of Poverty, My Life, The Secret History of the American Empire, Understanding Power, Good to Great, and The Giants of Enterprise). One of the key principles of The Secret is the Attitude of Gratitude. Gratitude is such a tremendous power for good–and I’ve learned that in the past I have not shown nearly enough of it.
11. Humans have a deep desire for love and affection in their lives. It is so nice to have someone to make you eggs and toast (metaphorically). One of the nicest experiences I had in 2007 was when a women I was dating made me eggs and toast for breakfast in bed. It felt so nice to have someone to care about you in that way. I’ve found that this desire for human affection and love can sometimes cause someone to stay with an individual that is just not right for them in the long term, if that person does provide support and affection.
12. If you are going to meet someone for the first time, Google them first. Find a couple topics for discussion prior to meeting someone for lunch. Take five minutes to learn their background whenever possible. I have gone into a few of the business lunches I had in 2007 without knowing a thing about the person other than the company they worked for due to being rushed prior to lunchtime. I have made it a point to review my next day’s schedule before I go to sleep each night and do any needed research on people then–and this practice has been helpful.
13. My definition of love is different than that of most. I define love as a ‘deep personal care for an individual.’ Thus I tend to love anyone that I truly care about and very much enjoy spending time with. Thus I found it very possible to love multiple people at the same time. I’ve learned that many others feel that you can only truly love one person at a time. While I agree with this statement in terms of physical love, for me I find it possible to love two or three people at any one point in time. As this can often frustrate the heck out of women I’m dating, I’m trying to figure out a way to reconcile the many forms of love and express the difference between loving someone and being in love with someone, which may be different. I’ve learned that I have to be very careful and explicit in how and when I say I love you to a women because of this difference in definitions.
14. Be real, smile, connect. Don’t just talk about business. One of the most valuable lessons I learned in 2007 was that my natural ‘expressionless’ face often looks like a ’stone face’ and can intimidate people or make people think I am cold-hearted. I was completely unaware of this. I learned the lesson from feedback I received at the Grinnell Leadership Seminar in August in Chapel Hill. I learned instead to be real with people, relax, stop being so serious all the time, and to not just talk about business–to not act like the whole world is always on my shoulders. I also learned to let my free child out, live through my heart more often, and to ‘Ride the Dragon’ when times are difficult. I learned from my roommate James that I can often be very intense and serious immediately when meeting new people as I would immediately inquire about their passion and want to talk about business, current events, poverty, war, social entrepreneurship, politics, or religion rather than less intense topics like music, movies, food, or games. I’ve learned with the help of my friend John, the Grinnell group, and James to be less serious–at least initially when meeting people. I’m still working on getting rid of the stone face, chilling out more, and being more real–while still working hard and getting things done.
15. Share your passion with people. Another lesson I learned at the Grinnell Seminar was to share my passions with people. I often was afraid to share my passion with people in business settings due a feeling that it was not fully relevant to the business. My passion is learning about and working to reduce global poverty and human suffering both at home and in developing countries. On day three of four of the Grinnell Seminar we were asked to share our passion. They told me that when I did this my eyes lit up and I became real to them. I then learned the most important lesson of all–that they would much rather follow that passionate person with eyes lit up than the stone faced serious leader they were exposed to on days one and two. I’m still working on figuring how and when it is best to share my passion with others, but feel the mental freedom to do so has been a bliss.
16. Marriage is very rarely perfect. Growing up I believed marriage to be a union between two people who were destined to be together and that other than the rare argument, marriage was generally perfect. Seeing the interactions and hearing the stories of many married couples, I now know this to not be true and that a successful marriage takes at the minimum tremendous communication skills on both sides, generally overlapping life plans, and a willingness to compromise with one another.
17. Love and good health are the two of most wonderful things God created. While I believe the purpose of my life is to be happy, help others, and create further life–two of the absolute best things in this world are love and good health. Humans spend more time and money working to acquire and keep both than any other two substances. Love can surely move mountains.
18. A Great woman can make a huge difference to a Great man. I’ve seen this be true in many of the biographies of leaders, Presidents and Captains of Industry that I’ve read in 2007 and seen it true in my own life.
19. Don’t lead women on. Even if you don’t want to ruin what you have now, don’t lead women on. It’s mean and not worth it to do so. I’ve learned this lesson in 2007. I was hurt by a woman during 2007 who I felt led me on. After I could understand what it felt like from the other side it became easier to no longer do–though I still was by no means perfect. I’ve still struggled at times with avoiding this behavior, but I am committed to working on it and being as upfront as possible about feelings–or sometimes delaying sharing feelings until after I know they are stable. Often my feelings are not stable and are tied to how I feel at the moment rather than how I feel overall. I’ve worked on being able to discern which type of feelings are which.
20. Don’t ever let your mind limit yourself. Just because you can’t understand how you’ll achieve any great goal–whether it is to become a billionaire, end world poverty, find a soulmate, or become a global leader–doesn’t mean you should not set the goal. As you progress toward your vision you will figure out how. Man often overestimates what he can accomplish in one year but greatly underestimates what he can achieve in five, ten, and twenty years.

Business Lessons

1. I have to solicit cross-team input in order to get it. I’ve learned that input and feedback from team members has tremendous value and have learned that it is often difficult to get enough of. I learned to proactively seek it through surveys, skip-level meetings, and pulse-check lunches, discussions, and coffees with different staff members. I found that the best ideas very often come bottom-up.
2. A percentage of people will always criticize you regardless of how you perform. I learned in 2007 that regardless of how well you are performing, a small percentage of people will always be critical of you. In the political world, if you can achieve a 60% approval rate you’re doing a tremendous job. It is very difficult to operate in a world in which 40% of people don’t approve of what you are doing–but I’ve learned it comes with the territory of a leader.
3. Stop worrying so much about what people think of you. Just be different, work hard, and get results. Be concerned with what you do and make sure it aligns with your values and principles, but don’t spend endless mind cycles worrying about what people think.
4. You need to have thick skin and persistence to succeed in this life. I learned from my friends Carolina that you must be direct and upfront with people to get what you want in life. I’ve learned through my friend Joktan and my CFO Tim that you often have to negotiate what you want in life. I’ve learned further through enduring criticism that one must have thick skin, perseverance, and persistence to succeed. There will always be someone coming after you.
5. Our team is extremely valuable to the company. In the beginning it was just me and Aaron. Then we added Josh, David, David, Brad. Today we have 80 team members and are growing. I’ve learned that the value of our team is immense. We have made many investments in better benefits, more vacation time, stock plans, and conscious culture-creation for the team and every time the investment has paid off in creating a family that is happier and more productive.
6. Slow times should scare you. While slow times are rare at iContact these days, in the past few years we have had 2-3 slows times that I noticed–periods of 3-4 weeks in which not very much was happening either due to Holidays, vacations, product cycles, or coincidence. In every case, we’ve had an issue underneath the surface that came out as soon as the slow time ended. I’ve learned that whenever I feel there is a time that is slower than usual, to work extra hard and spend and extra time listening to what’s going on at the staff level of operations.
7. Randomly tell people that you appreciate them, that they are doing a great job. People don’t get enough praise. When someone is doing a job well, mention it to them. Don’t let your only interactions be interactions in which you suggest different behavior.
8. Attack issues head on. Be direct and communicative, not passive aggressive when addressing issues. Take a couple minutes to think then act immediately. I took the time to have a three hour late-evening meeting with my partner Aaron in May to clear up some issues we were miscommunicating about before an early morning flight to New York the next day. Holding that meeting was very helpful to our alignment and continue positive interaction. While I’ve not always been successful in doing this, I’ve learned to take the time to meet with people in person to clear up any issues as soon as you detect there may be an issue.
9. It can be very helpful to fundamental investing results if you have an understanding of global macroeconomic trends and causes. Understanding why currency values, interest rates, and commodity prices fluctuate has been very helpful in determining which personal investments to make. The basic lesson that when interest rates go down in a country while a budget deficit rises, currency values will also go down in a country has made Warren Buffet quite a lot of money in the past two years. The great value of a liberal arts education in hindsight is that you can more easily see the bigger picture of how the world operates. Markets are by no means efficient and he who has a perspective that others cannot see will be able to produce premium returns. Now if I could only predict where oil will be in five years. A financial planner friend of mine thinks it will be at $60 per barrel due to the large supplies currently being found and the lag between the time higher prices cause higher technology investment and when higher tech investment causes an increase in supply. Personally, I don’t see any way the price of oil will do anything but go up in my lifetime with a limited supply and demand that will increase many times over before we are able to greatly eliminate dependence on oil as a source of energy.
10. It can be very helpful to fundamental investing results if you can have advisors that set policy on your team. By watching a documentary on the Carlyle private equity group I learned that you can get great returns if you know what the policy and government interaction is going to be on highly regulated industries like defense in advance and you have former Presidents and Secretaries of Defense and State working for you.
11. Don’t make people feel like you are going around them. Skip-level meetings are often very helpful (where you meet with people who don’t directly report to you in order to get a better pulse on the business) but be sure to explain to the person who reports to you that you are theoretically going ‘around’ why you are doing what you are doing and that it is not caused by anything they are doing wrong. Unless of course it is–in which case you need to talk to them about what’s going on right away anyway.
12. Don’t make people feel you are consulting others about their field without them. If you are going to consult with someone outside your company about a topic you have someone in charge of, tell the person in charge of the department what you are doing and why in advance and either invite them to join you or meet with the person afterwards or explain your reasoning why you’d rather meet with the person alone.
13. Speed of implementation matters. Cutting just a day off each stage of a project can save a week of time or more by the time a project is done. Weeks of time saved can greatly increase customer acquisition and internal efficiency. Encourage your team to get one additional thing done before they leave in order to reduce time delays from projects. The very large majority of ‘real hours’ (versus ‘human hours’) spent on a large project is time waiting on persons to review, approve, or provide the next part of the project. It can take many extra weeks to complete a project that only requires only a few hours of human effort if each phase waits in the inbox of an individual for three days instead of two.
14. Take the time to explain to people how your thinking process works. I once felt that because I was CEO I was justified in making small decisions (like the background color or text font face on a web page) without taking the often extended amount of time needed to fully think through and explain my reasoning. I learned that while I may have been justified, I found that things would get done better and more effectively if I did take the time to think through and explain my reasoning fully.
15. Always create a competitive round when you are raising VC. Work to get multiple term sheets when you raise venture capital. Our pre-money valuation increased a full 50% from when we received our first term sheet to when we received our fourth a couple weeks later in May. There really isn’t an easier way to create perceived value than to get competition in a round. If you can create a parallel process and receive multiple term sheets you will have more power. Group mentality does at times take hold, causing the valuation to be bid up with multiple players in the deal and some of the secondary terms to be softened.
16. Have comparables ready when talking valuation. Be prepared with revenue multiples from both public companies that are similar to yours and private comparables. Depending on many factors (team, technology, industry stage, revenue growth, market size) one can expect to be able to raise funds at 2x to 10x your revenues from the trailing twelve months or 1x to 4x your projected revenues from the next twelve months. If you don’t have any revenues yet, the valuation will be whatever you can negotiate with an investor and based upon your experience and any intellectual property you have. At the end of the day, the market valuation for your company is what an investor is willing to pay—and as such it is important to have multiple firms competing to invest in your firm if possible. Depending on the stage of your company, you may be able to raise funds at a 30% to 70% discount off the public market trailing or forward revenue comparables.
17. When giving VC presentations, prepare well and give a knockout presentation.. Invest in a graphic designer to make your presentation look nice and go heavy on actual examples of customer use and light on complex slides. I have seen a short flash product demo video or customer video interview within the presentation work well. Don’t let any slide have more than five bullet points or fifty words.
18. When negotiating raising investment, have a top tier legal advisor on your side. Once you receive a term sheet, have your attorney review it right away and provide feedback before you discuss it with the investment firm. Your negotiating power will be based upon how much you need the money, the reputation of the firm, your reputation as an entrepreneur, any past successes you’ve had, your experience, the quality of your management team, the members of your advisory panel, the size of your addressable market, your market timing, the quality of your technology and IP, your ability to walk away; and whether you have other competing term sheets.
19. Make sure you know which terms are important to you in term sheet negotiation. Generally the valuation, option pool size, liquidation preference, participating preferred, founder revesting, and preferred stock veto rights are the most important terms to negotiate. You may wish to have your attorney or CFO if you have one negotiate the finer points directly with the firm’s attorney.
20. The investment firm providing the highest valuation isn’t always the best firm to work with. I learned that there are many important factors in a venture capital deal. The most important is not the valuation, but instead whether you have good chemistry with the firm who wants to invest and in particular with the person who would be joining your Board of Directors. You will create, or destroy, much more value in the years following the investment by having the right person on your Board and the right firm backing them than you will by going with the firm that provides the absolute highest valuation possible. The other downside of pushing up the valuation beyond what you feel is fair is that the ‘winning’ investor will often ride you much harder to justify their higher purchase price–often creating lots of stress that simply is not worth the cost.

2007 By the Numbers

The next few days I’m going to be writing some posts reviewing this past year.

In 2007, I’ve received 61,457 emails, sent 13,174 emails, spoken in front of approximately 3,445 people at 25 speaking events, received 928 Facebook messages, sent 601 Facebook messages, wrote 181 blog posts, had 135 business lunches, held 83 employee interviews, been on 49 airplanes, talked with 46 venture capital firms, visited 28 cities, attended 27 business dinners, had 20 press interviews, held 11 Entrepreneur & Social Entrepreneur Meetups, read 9 books, been to New York City 5 times, added 4 roommates to our house of entrepreneurs and social entrepreneurs, lost 3 phones, been on 2 magazine covers, been on 1 national television show, and completed 1 book manuscript.