I like the concept of being explicitly accessible to others in my industry. One of my favorite parts of being in the NYC tech/start-up scene is that almost everyone is reachable. I like meeting new people who have common interests, especially when they bring the fire and passion that seem to be in the DNA of so many great entrepreneurs. I often tell people that digital, sports and start-up/career path are three things that fascinate me and that I can talk/think about that stuff all day long. So I’m pretty sure that my office hour sessions will be interesting, at the very least, with the potential for me to learn about new stuff, expand my network and build relationships.

Last week I attended my first office hour sessions with Aaron Cohen at the swanky new co-working space General Assembly. Aaron is a serial entrepreneur who has founded multiple companies and has also been the CEO of Bolt Media and Menupages. I wanted to chat with Aaron abut local media but we hardly even touched that topic as the conversation veered in so many different interesting directions in the 20 minute scheduled time block.

I then held my first office hours last Friday at my office and had the pleasure of speaking with two different young and bright people who have interests in digital sports. I learned more about their current jobs and interests and hopefully shared some worthwhile advice. I enjoyed it.

I sometimes get hit up my friends/acquaintances that need advice with a digital or business idea or project. I try to tell them that the best thing to do is for us to schedule time where I can give my undivided attention and focus to helping out. Hopefully, office hours can be used for this as well.

I plan to hold office hours bi-weekly. It will probably be in the early mornings during the week as my day usually doesn’t get busy until 10am. My schedule will be posted on Ohours so come visit me and/or pass this on to anyone else who might be interested. My next scheduled office hours are this Friday (4/15) at 9am.

Alas, I would be remiss to write this post without mentioning that Ohours was created by my digital buddy and dodgeball teammate Nate Westheimer. Nate is a natural connector and facilitator and, despite being from Cincinatti!!, is one of the true leaders of the NYC digital start-up scene. He led the NYC Tech Meetup for a few years. After leaving his last venture, Nate declared that he needed to learn how to code in his HoPE Manifesto. In a matter of months he did just that and Ohours is his first project as a developer. I love the practicality of what he built, as Nate has been holding weekly office hours for a few years now and recognized the need for a better tool for people to connect, schedule and meet for office hours. If you’re interested to talk to Nate, sign up for his Ohours!

Start-ups move quick so it’s tricky to keep all of my networks and contacts updated on our progress. For Sportsvite’s business partners and clients we regularly send out a corporate update newsletter. But I haven’t properly blogged about Sportsvite since the July 2007. So for all you lucky little Littyhoopsters out there you’re about to get it straight from this blogger’s keyboard…

Once upon a time, circa 2006, Sportsvite.com officially launched with the simple goal to make it easier for people to connect with each other to organize and manage their sports activities. We focused on adult sports because we wanted to create the solution to the very problem that we faced. I, for one, still have a yearning desire to brick three-pointers, pull softballs way foul, and run very slowly. Sports are well organized for youth, high school and even college athletics. But enter the world of adulthood, move to a new city, and start a non-sports professional career and it becomes considerably more difficult to play. In fact our original Sportsvite tagline was Stop Playing With Yourself. Sportsvite’s mantra is that playing sports is just as much fun for an adult. Our aim is to leverage digital and social media to make it easier to do just that.

Sportsvite.com has grown into an online community with over 150K registered members. It helps thousands of people play their favorite sports and activities. Sportsvite members can find other players, teams or leagues in their area. It also makes the life of a rec sports team captain a bit more organized. Along the way, we realized in order to make Sportsvite a scalable and sustainable business we needed to aggregate MILLIONS of players on Sportsvite.com. To do this, we needed to have an even bigger impact on recreational sports.

The first place we looked was at the local sports leagues (think the Urban Professional League or NYCSSC here in NYC). It was clear that these leagues are creating the opportunities for adults to play their favorite team sports. Over 1500 league organizations were using Sportsvite to create league profiles (NYC Partners) to promote their sports leagues to the Sportsvite community (similar to how a business or organization will create a profile on Facebook). This is just a fraction of the thousands of sport & social clubs, parks & rec, YMCA and private local rec sports leagues that can be found in every city, town and neighborhood.

Most league organizers operate as a type of local event producer. They secure field space, hire refs and staff, manage registration and schedules, communicate directly with team captains and players, and produce sports events weekly. We spoke with hundreds of sports league organizers to understand how technology could help leagues more efficiently operate and expand their business. Most league organizers simply didn’t have the expertise or free capital to invest in digital solutions.

In 2010 we launched LeagueApps. Our goal is for it to be the best digital solution to power adult recreational sports leagues. So far, the feedback and response has been promising. Since it was launched in the early fall over 25 leagues have joined the platform. Just this month we’ve launched new league partners in Miami (Miami SSC) Philadelphia (Philly Sports Network), Phoenix (Coed Sports Arizona) and Los Angeles (All City Athletics). Next we plan to work with our league partners to enhance the LeagueApps platform to improve the experience for their members. This includes social media integration, mobile functionality, team management features (death to the dreaded forfeit!) and e-commerce features.

Local sports leagues can be a valuable platform for brands and marketers that want to reach young, active adults through both experiential (at the field) and digital marketing efforts. Yet most leagues don’t have the audience reach or sales experience to secure sponsorship deals. Most brands can’t build a program that has enough size or impact for it to be worthwhile. So Sportsvite has networked these leagues together to aggregate an audience of active young adults. We call it the Recreational Sports Network and it allows our league partners to opt into brand sponsorships opportunities. Over 500 leagues have joined the RSN which represents 1MM+ adult sports players. Through the RSN, we’ve completed sponsorship programs for Clif Bar, Corona, Smokey Bones Bar + Grill, Buffalo Wild Wings and POWERADE.

As Sportsvite builds up its presence in adult recreational sports we’re also looking at other sectors of sports that can use a digital upgrade. Sports camps, AAU tournaments, church leagues, fitness clubs and youth sports are on the radar screen. Amazingly, many of the 5.5MM students that play college intramurals are still going down to the fieldhouse to sign up for their leagues with paper and pen!

We like to think about what the recreational sports world will be like in the next generation. I got to say it’s awesome. Every single at bat, jump shot, second serve and first down will be recorded digitally and shared with your friends, teammates and competition. Every player will have all their stats and results to see how they fare against their friends. Ask any recreational athlete if they would like to feel more like a pro. There answer will be a resounding Marv Albertesque YES. Hit a game-winning shot and read about it on a local blog. Win a league sportsmanship award sponsored by Mastercard…Priceless!

Once a person taps into their passion great things happen. By great things I’m talking about a fantasy sports league made up of your friends in your local rec sports league. Imagine that. Or look at it from a utility angle. How about a mobile app to find, organize or create a pick-up game on the fly by seeing who checks in at the local park.

In the future, everyone will have their 15 minutes of Sportscenter fame.

Here is mine…

How did this happen?

I’d characterize my most dominating personality traits to be independence, efficiency and free/stubborn thinking. For most of the last decade the independent side has driven much of my career direction. I’ve gravitated into entrepreneurial positions where I can better control my own destiny and have the freedom to carve my own path. Even within those positions, I’ve tried to isolate my performance from the rest of the team believing that otherwise I’d be slowed down. It didn’t help that I worked in unstructured work environments.

Now I’ve also always been driven by efficiency. In my schoolwork I was more concerned with doing the right amount of studying/work (judged by me) than with the final result or grade. Socially, I’m definitely on the lazy side of the spectrum. For better or worse this has also carried into my professional career. I don’t like to work hard unless it’s the only way to get something done. More often than not, I’ve been able to figure out shortcuts and this is much more satisfying to me. One positive is that I’m usually able to fully push my ego aside and focus on the end result or goal.

Finally, I’m a stubborn free thinker. I didn’t get accepted into my first five college choices. I was bummed out about it for awhile and one day my mom gave me that look that Brooklyn Jewish mothers have trademarked and told me that if I really wanted to get into any of those schools I could have. She was right. For whatever reason, I never bought into the path. I’d do it the same exact way all over again (Zelda, ayn rand, college hoops and fantasy sports over AP Euro studying= no brainer). I’ve had ample opportunities to follow easier career paths that could be less risky and more financially rewarding. I haven’t. I don’t want to just be successful by worldly standards. I want to be successful by my own standards (not going to get into what that means). I’ve worked in pervious organizations that have reached their goals but I was unimpressed by the way they did it. Right now, I’m kind of enamored with Tony Hsieh (Zappos) and Reed Hastings (NetFlix). They were both able to build successful companies on their own idealistic terms with their own ideal cultures.

As my career has advanced, I’ve started to realize that if I want to keep my independence it will limit my professional upside. A hired gun is just that – impactful and effective but lacking the real power of the person who hired him! Perhaps power and influence is more attractive than independence.

It seems to me that the best way to truly be powerful and influential is through management and leadership. A person who can galvanize a group of people to all work towards the same goal will always be stronger than the individual, right? I also believe that management skills are more transferable. No matter what situation, venture or project a leader can always use these skills they have developed. That seems way easier than trying to learn a new industry as well as I know digital sports media. Finally, I want to do things my way – and the only way that will happen is if I’m in a management position.

Even after writing all this mumbo jumbo I’m still trying to figure out why I’ve developed such a desire to be a leader. It’s a trait that I’ve never really exhibited before other than applying it to myself (and if I’m a leader of one than the jokes on me). I looked at the kids who were captain of my high school sports teams as ass-kissers or coach’s puppets. I never got why my buddy Hal wanted to be class president every year. Even now, very few of my friends/readers seem to have a strong prioritized desire to follow a leadership path (correct me if I’m wrong).

I’ve never had a truly great manager at any organization that I’ve ever been a part of. I don’t think this is uncommon though. A great leader is rare to find. It’s incredible difficult. It’s hard enough to manage yourself, get in your own mind, and control your own actions. Think about how hard it is to do that for a group of diverse people to all achieve a common goal.

I’m learning on the fly. I’m trusting my own instincts, trying to be extremely thoughtful, honest and soaking up as much as possible through blogs, books, conversations and advice. I’m hoping to develop a solid enough foundation so when I make mistakes I can recognize them and correct them with good decisions. I’m not a natural and for most of my life I’ve gravitated towards doings things that I’m naturally good at. It’s a weird feeling of self-awareness when I sense that I’m falling short. I try to challenge myself every day to be more considerate and less selfish. To show less frustration and more inspiration. To focus my thinking on the team and not myself. It’s my biggest professional challenge yet but hopefully I’m up to it.

It’s a bit scary for me to even put all these thoughts and ideas down on your computer screen (or in troy’s case mobile device because he doesn’t own a computer – no way you are still reading this triz!!). I’m not sure what I’m going to think when I look back and read this five or ten year from now. But I don’t think I’m getting any smarter or any sharper over the next decade (genetically, I’m destined to get fatter, snore louder and repeat myself more). But I do hope to become a better leader.

Recently, I’ve been helping a few friends think through there digital business ideas. One way to more fully comprehend a business opportunity is to create a simple pro forma income statement or business model. It’s practically impossible to predict what is going to happen with a new business so a model is used more for a framework to understand key drivers and help make informed decisions.

Most digital businesses derive revenue through E-Commerce (including affiliate fees), subscription products, or advertising revenue. Each of these revenue streams has a few key metrics that help project revenue. Once these drivers are recognized it helps clarify what exactly needs to happen to be successful. For example, digital advertising revenue is a product of visits, page views and CPM rate. A business model also provides a realistic projection of how long, and how much money, it will take to reach certain milestones (most notable profitable). This allows for better planning and cash flow management which is essential in the early stages before a business is profitable.

I created a very simple financial model template that can be used to project website revenue. While this model might not hold up in a meeting with a venture capitalist, it gets to the fundamentals of any website.

If you are in the process of creating a website, or are even thinking about it, play around with this and hit me up if you want to chat through it.

START UP FINANCIAL MODEL
Right click and “save as” the above link to download the Excel spreadsheet.

I do realize that all you Littyhoopsters are not necessarily as fascinated by the blending of jocks, geeks and suits. So I’ve attempted to venture out to find the right audience for these posts.

I syndicated my post on March Madness on Demand to The Wire blog that is part of the Business Insider Network. This is one of the top digital blogs on the web and is a neat way to get my name and ideas out there. I’m planning to write more about sports and digital for them in the future. It was pretty simple to set this up as I reached out directly to the Deputy Editor, Dan Frommer, and after swapping a few emails we had a basic arrangement in place that allows me to contribute. My first post was read over 250 times and retweeted 48 times. My friends Pete, Blake, Ellstein and Matt M. all spotted it on their own and it made me feel big time!

This week I (or whoever is Brian Litvak – without a “c”) had my blog post on a Freemium ticket model idea posted on CNBC’s Sports Biz Blog with Darren Rovell. The blog announced a contest last week to publish guest blog posts. Over 100 submissions were sent in and Darren and team published 14. My post was lucky enough to be selected. This post dissected the idea of a professional sports team giving away tickets in order to increase game attendence and fan base which a team can then monetize in other ways. I’m not sure if this plan makes economic sense right now (and no team has yet to try it) but it’s an interesting thought exercise especially since I believe sports is shifting from an event dominated medium to a media dominated medium. I received a bunch of comments and it was cool to see how people reacted. One guy commented that this was a bad idea because “half of the stadium is filled with homeless people, most of whom aren’t wearing team logos, don’t spend any money on food or parking, don’t smell very nice, and who beg from the other half of the crowd?”. I think this guy might be confused between my idea and the fans of Philadelphia.

By the way, Darren Rovell is from Roslyn (town next to Great Neck) and is just a few years older than me. I give him lots of credit as he single handedly created a niche in sports business reporting (first for ESPN and now for CNBC). He’s been super responsive the few times I’ve reached out to him over the years and therefore I’m not just a fan of his reporting but as him as a person as well. Plus, the Sahn brothers say he is a good dude.

Look forward to sharing some more of my ideas, theories and findings on digital sports business. Even if you don’t read it here, perhaps you’ll see it on the cover of the Wall Street Journal one day. I hope that black and white sketch of my face is pimp

I appreciate the opportunity to share who I am in more detail. It often seems quite difficult to learn enough about a person from one piece of paper or a short and structured conversation. Therefore I’m going to use some of my previous blog posts, things I’ve written long before I knew about this opportunity, to better illustrate my accomplishments and interests. Each link below leads to a blog post that I’ve written over the years.

WORK SUCCESSES

Promotions

• Every major promotion that I’ve earned in my career has led to a new position being created within that organization.
• At my first full-time position at OCSN, it took me a few months to realize I was more interested in how I could help the company generate new revenue streams rather than update web pages as a web editor. It took a few more months for me to meet, greet and successful pitch the executives in the organization to create a new junior business development role for me.
• After OCSN was acquired by CSTV, I was the first person in the OCSN Carlsbad office to move to the CSTV New York City to help develop CSTV’s digital business.
• After working on March Madness On Demand and launching a college fantasy football application (profitable in its first year) I was promoted to Director of Online Business Development to focus on online gaming and community. I was the youngest (and most inexperienced) Director in the organization and reported directly to the CEO.
• As the first employee and part of the founding team at Sportsvite, I’ve grown with the organization. I am part of the management team and now take it upon myself to improve in my leadership and management role while running business development, marketing and sales and contributing to overall strategy.

Management

• As part of the management team at Sportsvite, I currently lead a team of three people (was as high as five) for marketing partnerships, customer acquisition and sponsorship/advertising sales.
• I developed an intern program at Sportsvite (cheap, smart brainpower is invaluable to a startup) in which over ten interns have successfully completed with many going on to take full-time positions in digital media.
• As the youngest Director at CSTV, and with no direct reports or budget, I had to manage up and laterally to secure resources and support to lead digital projects in creating a blog network, podcasting solution and college fantasy football application.

ACADEMIC SUCCESS

• Entered college with 38 credits and sophomore standing due to Advanced Placement courses and test results in high school.
• Accepted into undergraduate business school at University of Michigan (2-year program) and graduated with a BBA degree with distinction (3.5 GPA).
• Completed independent studies in online marketing for a local laundry mat and a search engine optimization project for my own college basketball website, Littyhoops.com
• Volunteered at local elementary school and worked as private tutor (5-10 Hrs per week).

LEADERSHIP

Work

• I believe every startup needs a true leader to instill confidence in the entire team and to pave the way to success. I’ve tried to grow into that role as Sportsvite has matured by leading our business units, making personnel decisions and managing investor’s expectations.
• When I first started at Sportsvite I had no experience in the interviewing and hiring process. I’ve now hired 5 full-time employees and numerous part-time resources and interns.

Littyhoops Blog

• My personal blog has developed an audience of 100 email subscribers that consists of family, friends, colleagues and others. I often try to write about topics that are as interesting to them as it is to me. Things like business networking, failure, and personal growth. This leads to both online and actual conversations with others who share my interests. There are so many great reasons why I love to blog.
• As an early digital adopter I have shared my thoughts on new digital products or services including Twitter, Kayak, Hulu, Kiva, DonorsChoose and even
  ChatRoulette!

• I also write about trends in digital, advertising and media as well as emerging opportunitis in local, television distribution and Facebook.

Digital Media & Sports

• I’ve organized and hosted multiple events in digital sports including nextSports and the first Sports Marketing 2.0 event.
• I’ve authored guest blog posts for Business Insider including this recent post on the new NCAA media rights agreements with CBS and Turner.
• Presented this presentation to Wharton Entrepreneurship and Venture Capital Club

Littyhoops College Basketball Website

• Created Littyhoops.com college basketball website during college (before there were blogs!) and taught myself development and design skills, created content and managed online marketing, SEO, Adsense and partnerships.

My First Job

• I worked for four years during high school for the Police Athletic League. I started as a referee and advanced to hiring and managing a staff of 10 refs each weekend to organize and manage sports activities at multiple field or gym locations in my town. I reported to the police officer in charge (who wrote me a college recommendation) and wrote my college essay about the values I developed from experience.

Sports Captain

• I’m the manager or captain of multiple rec sports teams each year. This sometimes thankless job is part of the inspiration behind the Sportsvite concept!

OTHER STUFF

Hobbies

• Started a book club and have a blog recapping the books that I read.
• My favorite authors are Kurt Vonnegut, Ernest Hemmingway, F.Scott Fitzgerald and John Irving.
• Subscribe to multiple blogs that I read daily through Google RSS Reader.
• I consider myself a writer – thanks in large part to all my blogging.

Travel

• I’ve backpacked, and blogged, my way through Australia and Europe and have also explored India. My most recent trip was to Costa Rica. I’m trying to figure out how to get to Africa and the Far East next!

Professional Organizations

• Early member and active participant of nextNY organization. Organized multiple events in digital sports and held first feedback focus session.

Sports

• I play on numerous recreational sports teams including basketball, multiple softball teams and a dogeball team consisting of nextNY members.
• Training to run a sprint triathlon this fall.
• I’m a huge sports fan and spend a chunk of my free time obsessing over the Yankees, Knicks, Giants, University of Michigan sports and St. John’s basketball. I’m a collge basketball fanatic and take a family trip to watch the NCAA tournament every year!
• Yes, I’m addicted to fantasy sports as a participant and as an amazing business opportunity. I’ve recently contributed to the creation of one of the first twitter-based fantasy sports games.

Volunteer Work

• Part of Big Brother/Big Sister type mentorship program during college.
• Interested in creating my own charity or foundation and becoming more involved in social entrepreneurship.

If this blog post seems like I’m tooting my own horn that’s because I kind of am. One thing that I’ve learned from working at a startup is that there’s nobody else to toot your horn for you (especially at the start). Most people just see a pile of scraps and raw materials and it’s your job to convince them your building a Delorean DMC-12. The only way to do that is to believe in it yourself. This doesn’t happen by boasting, bragging or having all the answers – but rather from being honest, passionate and willing to listen and directly answer all their questions.

I often think about how I should position myself to others. Many people that I speak too don’t feel like they do a good job of concisely and effectively sharing who they are and what they want to accomplish. It’s hard and it takes some planning and practice. Next time I need to do it I’ll have this blog post (both in my mind and right here) as reference.

Small business owners have long ago figured out the key to advertising and marketing while brilliant MBA’s, award-winning agencies, and self-proclaimed “marketing gurus” hopelessly manipulate the 4 P’s of marketing into buzzwords of mass destruction. The simple principle: only spend money if it leads to making money!

Local businesses are advertising the same way that they did a decade ago. This includes the obligatory phone book ad, penny saver coupons and local print publications. If they want to go Hollywood (think car dealers) they pony up with a super cheesy thirty second radio or television advertisement. Case in point…

Until recently, there have been few truly effective (effective = money making) digital platforms for local small businesses to advertise efficiently. The one true success, Google, happens to also be the greatest company of this generation. For those who think Google is just a nifty tool to help pickup French chicks, the true value is that it enables businesses to place small text ads on relevant search result pages AND allows the advertiser to easily track the result of their advertising expense. But there is a tremendous opportunity that goes way beyond Google. Just ask your local pizza place, neighborhood bar, barber shop, arcade or bowling alley. My guess is that many small business owners just aren’t nerdy enough to be advertising through Google. In fact, small businesses often look at their web presence as a cost center in which they have to pay to develop and maintain their own website rather than as a revenue generating marketing play.

New digital start-ups try to conquer the local space because of the vast untapped market but the well runs dry before they ever see substantial advertising revenue. Dating back to the dot com days with Microsoft Sidewalk, to hyperlocal news sites like Backfence.com and experiments from the Washington Post, the local space has been a digital albatross. The cost to create local content far outweighs the non-existent revenue from the zipped pockets of non-digital local business owners.

Thanks to the ever-evolving digital landscape, local businesses now have a plethora of digital resources they can use to help drive sales. Restaurants have an increasingly significant reputation to maintain on review websites like Yelp, Menupages and Citysearch. Businesses can use Facebook fan pages combined with highly targeted facebook ads. Twitter is a fluent platform to instantly connect with customers. There is also a renewed focus and investment in local email newsletters (Thrillist, Urban Daddy, Flavorpill and enhanced television and newspaper websites. To take the place of failing print media companies, local news (Everyblock, Patch) and relevant blogs and blog networks (Outside.In, Placeblogger) are taking their place. An even more promising development is the progress of the mobile web which is naturally location conscious. New apps like Four Square, Loopt and even BBM have tremendous potential to connect advertisers with potential customers. This NY Times article does a good job sizing it up.

Before we all have a neighborhood block party let’s realize it’s going to take at least another decade for Joe the Plumber or the average small business owner to be digitally-aware enough to do their own online marketing. This creates a neat little digital black hole.

Great local digital applications for users.
Meager local advertiser revenues.

In this situation I think the middle man wins. Who or what can help local businesses advertise digitally through the many new local platforms? How can that scale by city or neighborhood? I don’t think an individual publisher or platform can scale on its own because the unit economics don’t work. By that I mean that the cost of monetizing in an individual market is greater than the current revenues generated from a limited local audience. But if the local sales costs can be reduced, or the audience better monetized, then the unit economics can make sense for individual platform/publishers. I don’t think the “middle man” is a marketing agency. That is too manual for the digital world. More likely, the “middle man” is some kind of automated market place that allows local businesses to efficiently spend on local advertising and see a positive ROI. Yeah, that is kind of similar to a Google Adwords model. But it doesn’t overcome the friction of bringing the non-digital small business on to the web. For once I don’t have all the answers! I would love to understand Google’s local strategy.

I’ve become a true believer that Sportsvite’s success will lie in local. Participating in recreational sports is inherently local. No matter how well we can aggregate a recreational sports audience, the most value to marketer’s lies in how Sportsvite can influence their local activity. As Sportsvite captures the attention of players within their community, it is creating a highly effective marketing platform. Now we just need to understand how to reach the local advertisers and then scale to just about everywhere!

Those who are not familiar with the startup culture in their own industry or city are sometimes uncertain how to uncover and evaluate career opportunities. Luckily, it’s not all that difficult to get up to speed. Entrepreneurs are eager to see their friends or associates take the plunge into the startup world. Just be persistent, energetic and resourceful…and by doing so you’ll prove to yourself and to those you connect with that you’re ready for the challenges that lie ahead.

I’ve been planning to write specifically about how one can evaluate a start-up opportunity. Then the other day my superstar dodgeball teammate Charlie O’Donnell wrote an interesting blog post about the misconceptions of MBA’s who are interested in startup opportunities. If you take MBA’s to mean anyone with a distinguished corporate/legal/b-school background that is looking for a mid-level to sr. opportunity than his post covers most people that I have connected with as well. I urge you to read it (and the comment discussion) before you continue on.

Let’s just assume that you’ve proven your value to a startup and now you’re evaluating an opportunity to join a young company. This is a bit more complex that evaluating a corporate offer where the clearly defined levers are the company reputation, salary/cash compensation and position/role. But in a startup, this can be shrouded in smoke murkier than the black stuff on the island . When I was evaluating different startup opportunities (before I started at Sportsvite), I felt overwhelmed trying to figure out which was the best one for me.

Last week I was helping my intern make a similar decision. He is contemplating a move to San Francisco to join a small ad network and was trying to determine if it was as good a fit for him as his Lehigh wrestling uniform was in college. We developed a framework of issues to resolve in order to make a comfortable decision. The key fundamentals of this are company, position, compensation, intangibles. He then worked through the issues, did the research, and dug for the answers he needed to make an informed decision.

I thought it would be worthwhile to share this framework.

Startup Status
Assuming you like what the company actually does it’s important to also understand the current state of the business. Startups come in all different shapes, sizes, philosophies and funding cycles. It’s important to understand where the company is in its growth and where it hopes to go. The obvious and easiest thing to do is learn how many employees are in the company. But that can be misleading, and I would suggest digging a bit deeper to understand the company’s funding and financials.

A startup that is venture funded often means that it has an exit strategy, specific goals with deadlines and some kind of management/organization structure already in place (although this will undoubtedly change in the future). Even the funding round (Angel round vs. Series A or Series B) or investors can hold clues as to the company’s projected path.

In terms of financials, key metrics include current revenues, burn rate and proximity to its break even point and subsequent profitability. This information can help determine the best case and worst case scenarios for the startup as well as the timing for those milestones.

Questions/Issues

• How is Company X funded and who are the current investors?
• Does Company X plan to raise future rounds of finance? When? How much?
• What is the projected growth of the team? What are the next hires/positions?
• What are the revenue goals this year? What is the 5 year plan? (Even if you don’t see specific financials it’s worth a discussion)
• What companies are your closest competitors? What startups have been successful in this space?

Position/Role
A startup is like a sports team. Not only is talent important, but every person needs to play a specific role in order for it to be successful. It’s super important to understand the exact position and make sure it’s a perfect fit. An All-Star point guard isn’t going to be effective on a team that already has a great point guard but needs a big man. Since most Startup organization are still small (less than 40 people) it’s not impossible to get an understanding for how you would fit within the entire organization. Speak to both people above and below you as well as others in lateral positions (since many startups are often flatter than large organizations) and you’ll learn a lot about the organization as well as the culture.

It’s good to begin a dialogue to understand how this position might evolve as the company evolves. In early stage startups, people are often asked to wear more than one hat. If the position includes both marketing and business development duties, find out when they eventually plan to hire someone and what role that hire might play. Also, if you come into an early stage startup (less than 10 people and early in its funding cycle) realize that there is a very good chance they will hire above you as the company matures. That means you can start by reporting directly to the founder or CEO but soon find yourself separated by one or multiple levels as the organization expands.

Questions/Issues

• What do you envision the perfect employee to be like?
• What are your hesitancies/questions with me fitting into the role/team?
• How do you see my position evolving in the future?
• Will I always report to you?
• What do you expect from me above and beyond the job description?
• Would it be possible for me to talk to other people in the organization?

Compensation
Startups are ALWAYS cash-strapped. If they act like they aren’t, that probably means they are wasting money (and that is cause for concern). When I joined CSTV, I figured they had millions and millions of dollars to spare since they had raised a staggering amount of capital from high profile investors. But I soon learned how severely we were burning through cash and how tightly we needed to stick to meager budgets. Since most startups aren’t profitable, it’s a race to get revenues up in order to be profitable or exit before the company runs out of capital. The more a startup keeps down their costs the longer they can go (kind of like a patron in the champagne room).

This means that the base salary will be low. It’s going to be lower than what your market value is in the corporate world. If you are in a revenue generation position, you might be able to negotiate higher commission or bonus structure.

To make up for the salary disparity (and to give employees a stake in the game), startups often offer equity in the company to their employees. I’ve found that it’s very difficult to understand the value of equity agreements (which is already uncertain since it’s usually based on the value of the exit). It’s difficult to quickly get up to speed on equity agreements so its important that you request all the proper documents (equity plan, corporate operating agreement, capital structure) and have somebody who has experience (either a lawyer, VC, or startup veteran) to review your equity agreement and help decipher a potential payout in different scenarios (which might depend on additional funding, that could lead to dilution, and exit value). As I was trying to understand my equity plan at svite, I actually found myself in a private email chain with Fred Wilson and Brad Feld (Two of the most successful venture capitalists in the world) and both agreed it is an incredible complex, unique and cloudy topic. Even with both their advice I was totally confused.

If you agree to an equity plan, make sure you sign all the appropriate documentation BEFORE you begin. If the company is in such an early stage that they haven’t finalized documentation, have your own lawyer put together a document that outline the agreement.

Questions/Issues

• Obtain copies of the equity documents; operating agreement and capital structure (at least understand the employee stock pool and amount of outstanding shares at the current valuation)
• Understand if bonuses can be taken in cash or equity?
• Discuss salary increase philosophy (influenced by additional funding, individual or company performance)
• Ensure that health benefits, retirement plan, expense account, etc. are aligned with expectations or assumptions

Intangibles
My most important advice is that you need to BELIEVE in the company and be PASSIONATE about it. The honeymoon ends as soon as you tie up your laces and start chopping wood (only to realize your Ax is plastic and made by Fisher price). A startup is a roller coaster ride and you need to make sure that you stay committed during the dips. The best way to do this is to truly believe in the mission, team, and eventual success of the company. Believe in the founders, in the management, in the concept and in the strategy. If you join a startup thinking you can do it half-ass or just go along for the ride then you are as off as a Chris Duhon three point attempt. As Charlie wrote ” If someone is hiring one of the first 10 or 20 or even 50 people in their company, they need to be awesome. You can’t hide in a startup and there’s no room for dead weight or mailing it in.”

Sometimes, there is room for some flexibility in a startup organization and you can actually influence some of the details that might be set in stone in a bigger organization. This includes vacation time, ability to work from home, computer and equipment budget, etc. In many startups your job becomes your life so it’s important that it’s comfortable for you. The perfect time to negotiate this is when you know you want the job but before you accept. These sweeteners can play a big role in your overall happiness. Do realize that as the company matures some of these perks might need to be adjusted.

Questions/Issues

• Do I believe in the founder, team?
• What is the background of the members of the team?
• Who in the organization has startup experience?
• Does this keep me up at night with excitement for the possibilities?
• What do I think I will learn here?
• What are the risks? What are the rewards?
• If the company fails, where will that leave me in my career?
• What will I do with all my chedder when we hit it BIG?

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Hopefully, this is a helpful framework to better understand and evaluate startup opportunities. I know I’m missing tons of good information so please leave your thoughts or experiences in the comments. As always, hit me up if you want to chat through this stuff in more detail.

I have a few distinct memories of experiences with the World Wide Web that have made a lasting impression with me. They all happened in college. This makes sense as I really dug deep into the power of the web my freshman year of college when I first encountered high speed Ethernet in Mary Markley Hall. Before that I had to put up with the slowness of dial up and the wackness of the damn AOL busy signal.

I decided to create my very own website called Littyhoops.com in 2002. It was a college basketball website in which I voiced my opinions to the world and picked games. It was a glorified blog before there was such thing as blogs. Therefore, everything took lots more time to setup as I figured out how to code, host, design and manage the site on the fly. But it was all worth it because I loved the feeling of being able to broadcast my message to the world. All of a sudden, I had a soapbox to stand on that was high enough for anybody who wanted to watch. It boggled my mind that what I wrote in my basement apartment could instantly be shared with the world.

Another web memory I had during college was reselling Michigan vs. Ohio State football game tickets my junior year. The game fell on Thanksgiving that year and I realized that many out-of-state students would be going home for the holiday. I worked with my friend Dick B. to collect about 75 tickets and then went about selling them through eBay, craigslist and even a local website called Orange Sorbet. At one point we were selling $15 tickets for $150 each (then damn MSU and TJ Duckett upset Michigan on a phantom second). I would check on the auctions and my email every hour in amazement on how easy it was to sell the tickets and generate revenue. One day, Rich and I met up with a woman in an Ypsilanti restaurant who gave us $1000 in cash for a handful of tickets. I was scrambling to get rid of the final few tickets before I left town myself that weekend and actually somehow set up a meeting for my friend Kraz to meet a dude on the side of the highway to exchange two tickets for an XBOX (impossible to get at the time).

Finally, the third digital memory I have from college is creating a website for Robert and his nephew Robert who ran Champion’s – a local laundrymat/keg market/convenience store down the block from our house in Ann Arbor. Colby, Brodsky and I somehow came up with the idea to convince a teacher to let us do this as an independent study project (easy way to get a guaranteed A). We had fun with it. Posted a bunch of goofy photos, threw up some coupons and beer specials and Ben surely towed the line of indecency with his wily copy. We then “borrowed” some ridiculously large email list and sent an email blast out to every student in greek life (you could still do things like that back in the digtal stone ages). Instantly, the Robert’s saw an effect in sales from the website and email and they quickly realized the value of the website. Unfortunately, soon after Robert and Robert and us had an unfortunate falling out that included racial slurs and death threats.

All three are great memories on how I discovered the power of the web. While I enjoyed creating Littyhoops, I realized that the economics of that website sucked. I would need to increase my traffic by literally 500x to begin to sniff similar revenues as the other two projects. I was most captivated how I could make money from the Internet. It seemed magical. It still does.

So that was basically my long, over the top introduction to what I’ve been thinking about these days — digital business models. The common belief is that there are three ways to generate revenue online.

1) E-commerce
2) Advertising
3) Subscription

One of the very first things I realized at CSTV (and this probably holds true for any big media company) was that if I wanted to get anything new accomplished it better have some advertising dollars attached to it. (Incidently, his is why media companies got into a pickle by giving away all their content for free – they believed the best way to monetize was to grow audience and sell advertising around that aggregated audience.) When you work in sports media you quickly realize that it’s a never-ending cat and mouse game between sports properties and major brands looking to reach the mass audience of sports fans. Unlock brand’s advertising budgets in any way possible and the cash flows and you’re a hero.

Lately though, advertising hasn’t lived up to its billing. There are two main causes. The first is that the advertising market has gone into the crapper during this so-called Great Recession. Marketing budgets have been slashed as marketers are forced to evaluate everything and focus on proven tactics and ROI. The second is that digital advertising just really isn’t all the effective. With the exception of Google, which has an awesome thing going with search, most big brands don’t really understand how their website can help a brand be cooler (branding) or sell stuff (Direct response). Social Networks, Twitter, Facebook (virtual products? please!), blogs and mobile have had difficulty creating innovative monetization models to go along with innovative products, platforms or communication.

Chris Dixon wonders what happens if this is it for digital business innovation? What happens if all these breakthrough platforms end up monetizing in a similar fashion as AOL Instant Messenger? Groundbreaking behavior and communication product for sure, but not a business. That sounds like an industry that I want no part of.

Perhaps the ad market will soon make a comeback and easy advertising revenue starts flowing online again. Traditional media (print, radio, television) all got fat eating off the advertising world. Then in the 80’s cable television came along and innovated a new business model (charge cable companies for distribution of content). My gut tells me that digital is going to create new business models and not just borrow the advertising playbook. I’m more interested than ever in evaluating and innovating new digital business models. Link instant messenger, a great idea or product doesn’t always add up into a great business (especially in the digital world). I want to be in the business of creating great businesses.

E-commerce interests me. It allows you to buy anything from anyone at anytime. It makes efficient and fluid markets and increases transactions. Check out Etsy and buy handmade good from Africa and then think about what you are actually doing! In addition, the market share of people who shop online will increase. Children today view Amazon.com as Toys R’ Us or Wall Mart. E-Commerce has yet to be integrated with the social web. This blows my mind away how far we still have to go when it comes to e-commerce. I want to buy stuff that my friends recommend to me. That’s more effective than any advertisement I will ever view. I expect major innovation in the E-commerce space in the next stage of the web.

Mobile interests me. The utility ability of a mobile application is so powerful and so intimate. Most people have their phone on them at all times. It’s so valuable that the iPhone has been able to do something that the media companies could never really figure out how to do on the web. They charge for applications. The more the product is downloaded the more $ it generates. I like that model.

Subscription and micro-payments interest me. What kinds of digital services are people willing to pay for on the web? I’d love to offer something of such value that a consumer would lock into paying recurring fees to access it.

There are so many great ways to generate money on the web. My goal is start to learn more about some of these different opportunities. I want to talk to people who have non-advertising business models that are generating revenues and are profitable. What are they doing right and what are the fundamentals of their digital business? The tools that are available to an online marketer are as powerful as anything I have ever come across in business. I want to take advantage of that.

I no longer want to hear (or think) about great digital ideas or products. I want to focus on great digital business (and new money making schemes!).

I’m not at the point where I feel comfortable enough to share my career ambitions and goals in this blog post. To be honest, I’m not sure if I’ll ever have the desire to do that. But I do have a few things on the process and how I’m trying to figure it all out.

When I get an idea or concept like this stuck in my head, I usually think and think and then think some more and try to chip away at the issue until I begin to make sense out of it. I’ve always been thankful that my mind works in such a way that the more I focus on something the better I’m able to process it and feel more comfortable. I’ll usually try to clear my head and then think my way out of pickles or stressful situations. The nice thing about being a rational and logical thinker is that it’s easier to trust myself. I’m my own shrink.

Still, sometimes I need a mental boost to get me over the humps. Besides my father (who admittedly is clueless when it comes to today’s digital world) I really don’t have a mentor to turn too. So i rely on good conversations, things I read or even by connecting with people through this blog. I’ve had a few of worthwhile moments recently that I want to mention to ya’ll.

Recently, I’ve been playing career adviser for both of my sisters as they try to figure out their next career moves. I kind of give them the no holds barred brotherly lectures where I recite everything I know all at once in a condescending, know-it-all tone. The analogies I come up with on the fly with Courtney are frighteningly bad as I try to explain the same concept to her in four different ways just to make sure she grasps it exactly how I intended. Discussing and understanding their challenges allows me to realize and reaffirm some of my fundamental principles. Sometimes, solving other people’s problems can be the best way to solve your own.

Last week, I had lunch (La Mazouski) with Mia’s husband who now scares me with his intelligence and understanding of the digital startup world even more than he scares me with his flamboyant exuberance (penis jibbitz!). Jer has a combination of abundant energy and extreme restlessness that can get your gears turning. I find myself still thinking about some of the things we discussed one week later.

Finally, I read a blog post by investor and tech entrepreneur Chris Dixon this week. His blog is all the rage these days as he’s certainly distinguishing himself as a influencer in the tech startup community. Dixon used a classic computer science problem to discuss career path. I sucked at the only computer science class I took in college (got a C+ in C++) but the analogy clicked for me immediately. In my moments of second-guessing, I sometimes have difficulty reconciling the career opportunities that I’ve passed up and wondering if I made those choices for the right reasons. If an 18 year old Brian Litvack looked at a 28 year old Brian Litvack he might even call him an underacheiver (he would definitely call him fat). Chris’s blog post helped me put this insecurity into a larger perspective. It also has helped me better think through the entire topic of my career.

You can read the full blog post, and the comments are also worth a read, but here’s my favorite part…

A classic problem in computer science is hill climbing. Imagine you are dropped at a random spot on a hilly terrain, where you can only see a few feet in each direction (assume it’s foggy or something). The goal is to get to the highest hill.

Consider the simplest algorithm. At any given moment, take a step in the direction that takes you higher. The risk with this method is if you happen to start near the lower hill, you’ll end up at the top of that lower hill, not the top of the tallest hill.

A more sophisticated version of this algorithm adds some randomness into your walk. You start out with lots of randomness and reduce the amount of randomness over time. This gives you a better chance of meandering near the bigger hill before you start your focused, non-random climb.
Another and generally better algorithm has you repeatedly drop yourself in random parts of the terrain, do simple hill climbing, and then after many such attempts step back and decide which of the hills were highest.

 

 

Going back to the job candidate, he has the benefit of having a less foggy view of his terrain. He knows (or at least believes) he wants to end up at the top of a different hill than he is presently climbing. He can see that higher hill from where he stands.

But the lure of the current hill is strong. There is a natural human tendency to make the next step an upward one. He ends up falling for a common trap highlighted by behavioral economists: people tend to systematically overvalue near term over long term rewards. This effect seems to be even stronger in more ambitious people. Their ambition seems to make it hard for them to forgo the nearby upward step.

People early in their career should learn from computer science: meander some in your walk (especially early on), randomly drop yourself into new parts of the terrain, and when you find the highest hill, don’t waste any more time on the current hill no matter how much better the next step up might appear.