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7 Lessons From My First Year as an Entrepreneur

This is a great article from a fellow entrepreneur.

A year ago, I started Greatist with no real clue what I was doing. We’re now the fastest-growing health and fitness site on the Web, so a lot has gone right. But a lot has als0 gone wrong. A year ago, I’d never really hired someone. Never really fired someone. Never incorporated a company in Delaware. Never spent days accounting in Excel, signed an office lease, paid the IRS, saved a crashing website, negotiated with a potential acquirer, or been responsible for six people’s paychecks. But those things could always have been figured out.

The biggest challenges, instead, have been personal, and on that level, it’s never been harder. I’ve never been so busy, so behind, so unsatisfied with how much I can accomplish with the mere 24 hours in each day. At the same time, I’ve never been happier. I’ve never been more optimistic, more excited for what can be achieved, more able to genuinely say I love every second of what I’m doing. Now I can.

Here are 7 lessons I’ve learned this past year of being an entrepreneur:

Starting something for the first time is really, really hard. Imagine the hardest thing you’ve ever worked on. Now imagine that thing is the most important thing you’ve ever done. Then imagine you have no idea what you’re doing. Most startups are different, and most founder motivations and ambitions unique – but no matter what it is, if you think it’s going to be easy, you’re wrong. This experience has been way harder than anything I’ve ever been challenged with. I love that challenge. A startup is a to-do list with infinite scroll. It’s true that it’s never been easier to start a startup, but that doesn’t mean that starting a startup is remotely easy.

Sometimes you just have to make mistakes for yourself. There’s an unbelievable amount of brilliant, experienced entrepreneurs/investors/male models regularly sharing advice on the web ( Vin Vacanti, Fred Wilson, Mark Cuban, Chris Dixon, Ben Horowitz, Albert Wenger, Rob Go, Bijan Sabet, Brad Feld, Jason Goldberg, just to name a few of my favorites). Those + Quora can answer nearly any question. But you’re going to mess up anyway. I recognized that it was likely I’d make a lot of mistakes, but I’ve realized I had to make an awful lot of them for myself. Example: knowing that you should fire someone who isn’t working out because they’re hurting the team’s culture quickly is much easier than actually fully realizing that’s what’s happening and then acting on it. I knew, but I didn’t really know until I felt the taste of mistake in my mouth. And it tastes salty.

Asking others for help and meaning it is important. I’m the worst at asking for help, but I’m getting better. Entrepreneurs are, by nature, usually confident, positive and optimistic, but if success in startups is the outcome of a million random factors, inspiring help from others is among the most important. Asking for help is humbling, but the minute you genuinely eat your pride, tell it like it is, and share what you need is the minute things can change. If what you’ve built is truly meaningful and impressive, let your guard down. Share your hardest challenges, biggest worries and scariest fears, and people will help if they can.

Surround yourself with friends who will remind you you’re awesome when you need it, and call you out when it’s time. In my experience, entrepreneurship is sort of like a see-saw: sometimes it seems like everything is falling apart and, at others, that huge thing you’ve been working to achieve may actually be possible. Friends can be an escape, sure (and you need escapes, big time), but they can also be the external support you need most. It’s hard to keep up with friends regularly when you’re starting a company, but each time I do, I’ve been working increasingly hard to allow them to push me in the way I personally need pushing (and, by the way, try to do the same right back!).

Sharing what you’ve learned with others can pay back in a million different ways. With Greatist, I’ve found putting the time into teaching others has paid me back many times over. I started a class with Skillshare mostly because two awesome buddies, Peter Boyce and Scott Britton, asked me to. I taught How to Grow from 0 to 250,000 Organic Uniques in Under 6 Months with no expectations… and have since taught a few more. Each time I’ve been shocked by how much I’ve learned, from the people who take the class and those who follow up afterwards. I’ve made great friends, started major brand partnerships, been introduced to some remarkable people, and brainstormed amazing ideas with others because of them.

Schedule in specific time to think and be creative. Emails, meetings, sleep, repeat… and suddenly a week has gone by without time to think. This might sound a little silly, but put time blocks into your calendar to just think. I’ve literally just started scheduling “thinking time” on my calendar at regular intervals, and beg everyone on my team to do the same. Also, a lot of my most creative ideas come from doing, seeing, experiencing something else entirely. Some of my best ideas have come from seeing a random movie, attending a jazz concert, or taking the time to explore somewhere new.

The only way to build something different is to do things differently. A good friend, Runkeeper’s Jason Jacobs, said in an interview once: “We have no exit strategy, we have longtime horizons. We are digging our heels in and we are going to slog through this over a long period of time.” I’ve noticed it’s increasingly easy for people in the startup community to become swept up in, “That’s just what everyone else is doing.” It obviously makes some sense to do what others have done to fit how everyone else defines success, but I’m learning that success, to me, is different. I’m getting better and better at realizing that to achieve something different, we need to do different things.

To see think post as it originally appeared on startupnation.com, visit this link: 7 Lessons From My First Year as an Entrepreneur.

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How Long Is Your Startup’s Runway?

Why runway is one of the most important things for a startup founder.

From a simple Google search:

run·way [ruhn-wey]
Noun:
1. Strip of hard ground along which aircraft take off & land.
2. Raised aisle extending into the audience from a stage.

Let me suggest a third definition.

3. The amount of time a startup founder has to figure it out and make it happen before they have to give up and go find a job.

I was seeking advice from an experienced and cashed out entrepreneur the other day – perhaps pricing. He has a sales background and at his previous company he brought in $1 million in business before he took the plunge and quit his job along with his partners. They eventually figured out their business and delivery model and successfully delivered to their customer. He and his partners created for themselves a million dollar runway that gave them room to figure it out and make it happen.

My approach has been drastically different – we have built a product, a large database and a fabulous team – and in spite of single one client, for all intents and purposes we are pre-revenue. However I did start with a runway of my own. My runway is composed of personal savings and investments, for living expenses and funding the business, and programming, finance, and management experience that I am using to figure it out and make it happen.

Young entrepreneurs have the runway of youth and ambition, and a lack of bills and responsibility. Additionally they don’t know what they don’t know, so that makes them fearless and indomitable. That is all the runway they need to figure it out and make it happen.

My friend and I ended our conversation realizing that what we had in common was that we are both dead serious about doing this. We are not just dabbling around with starting up we are both trying to build companies and are willing to do it until we wrest some semblance of order out of the chaos that a company built from scratch can be.

This leads me to suggest a fourth definition:

4. The time a startup founder starts to spend a 100% of their time and attention on their company, in order to ensure that they do not run out of the same.

And this why, entrepreneurship and startups, in spite of surface challenges, are some of the most egalitarian pursuits out there.

As a woman you may have fewer men to relate to and learn from, or get a boost from just because they see themselves in you. But at the end of the day maybe you are more flexible and can find patterns or opportunities that men don’t.

If you are young, you have time on your side, and plenty of mentors who are older and wiser to look to, as well as very little to lose, but you will struggle with your inexperience in managing and in knowing what problems need solving.

If you are older, like me, you have experience on your side and real knowledge of problems that could do with an innovative solution, but you will struggle with an incredible fear of failure and have much more to lose on a real basis, not to mention a family whose future and well-being you put at risk.

But if you are a true entrepreneur you will learn to build from your strengths, and figure the rest of it out and make it happen. You only need a good runway.

This post originally appeared on Women2.org. To see it in its original format, click here.

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8 Ways To Get Press Coverage For Your Fresh Startup

Avoid Large PR Firms

Large PR firms are expensive and in today’s  digitally connected world, overrated.  Twitter, Foursquare, emails, and the plethora of other ways to find and reach out to journalists and bloggers removes the once impenetrable barrier to entry that required traditional PR contacts to crack. When you get to a size where you need a flock of PR professionals stewarding your brand across multiple geographies, hire a PR firm.  At least for the first couple of months, you can do most of the tasks yourself.  At Sparkology, we wasted nearly $20K on a relatively large NYC PR firm that paid little attention to us and our relatively small budget (another blog entry to come!). If you DO decide to hire a PR firm, really consider whether your needs will be better met by a large or smaller agency.

Prep Materials and Target Your Media List

In the past, you needed elaborate press releases, printed pitch decks, and long, formal corporate overviews (see where the $20K goes!?). Today, you just need to be ready with a one-pager that includes the product, company history, and a few lines about the founders.  You’ll also need some good screenshots.

Lastly, make your own media list.  Think about the goal of press.  Is it to raise awareness?  Target early adopters?  Bring in mass market consumers?  Backlinks for SEO?  Be realistic.  You may not get into WSJ, NYT, or Cosmo… but what about Mashable, a local CBS affiliate, or Springwise?  You should have a list of 20-30 publications, writers, and their email addresses.  Avoid generic email addresses like tips@magazine.com.  If you have a couple thousand dollars or a friend in PR, you can use a resource like Cision to get contact info.  If you’re on a budget, use all the usual stalking techniques: twitter, facebook, linkedin, old articles they’ve published, bio pages, about.me, personal blogs, meetup.com, etc.  Here’s a simple way to organize your media list.

Do a quick search of the writers’ work and biography to make sure there are no conflicts.  For example, we knew not to reach out to openly gay reporters because our dating site hadn’t included functionality for gay singles (but will in the future).  Similarly, male reporters who were college dropouts probably would not have liked our strict membership criterion that men hold degrees from top universities.  Neglecting to do this quick research can lead to embarrassing gaffes like this one.

Mine Your Networks

The first coverage of your startup will come through one of your team members’ personal connections.  This is the hustle.  Ask your friends on Facebook if they (or anyone close to them) know any writers/bloggers/journalists (and make sure you ‘like’ each other’s posts so that they get more visibility on news feeds).  Go on LinkedIn and type in the names of publications you are targeting as well as the big name newspapers.  Media is a very incestuous world – if you can get a meeting with any writer, take it.  They will probably know a way to make an introduction to the reporter you need.  Also, go into your college’s alumni database and perform the same searches you did on LinkedIn.  I’m batting a thousand or cold emails that have the words “Fellow UPenn Alum” in the subject line.

One network you’ve probably overlooked is that of your customers.  If your customers have personal profiles, scan them for press-related keywords.  If not, put a little popup on your internal pages that lets customers know you are looking for a connection to the press.

Note that the first publication to cover you does not need to be huge.  It just takes one “influencer” to read a blog, Reddit, or Hacker News and the story is everywhere.

Create Time-Relevant Content

We were taught this beautifully powerful tactic by one of the industry’s true PR mavens.  Journalists and bloggers have a content calendar that they need to abide by.  They need to put out a Dads and Grads story, something about love on Valentine’s  day, something about Christmas, etc.  Take a holiday that’s 3-6 weeks away and spin a story that relates your company to that holiday.  Or even better, create data survey your customers for data that relates your brand to that holiday.  For example, if you are a travel company and July 4th is coming up, poll your users if they would rather fly or drive to their destination.  Any writer speaking about coming home for the holidays will gladly reference your data!  Here’s an example of how we put this strategy to use for Sparkology.

Use Customer Data

See the theme yet?  The press loves data because their readers love data, especially controversial data… So find the data that goes against common perception or includes potty humor. OKCupid published an entire OKTrends blog where they spliced their data (and we’ve done something similar).  If you can’t mine interaction data, integrate a polling platform into your site.  We built a custom, convenient, and non-obtrusive polling platform, because we found that sending customers to survey sites like surveymonkey had low hit rates.  .

Become an Expert

Don’t have enough data yet?  You can still create meaningful articles by becoming experts in your fields.  If you’re a rockstar SEO hacker, detail some of your SEO strategies.  You can even use your platform to encourage other industry experts to opine and generate valuable content.  For example, we run a monthly expert panel where America’s top dating experts give their opinion on a single topic.  Not only are their followers introduced to our service, but their strong opinions make for great press.  Both you and the experts benefit from the additional exposure.

Pay for It. Or Don’t.

Reputable newspapers have strict boundaries between editorial and sales departments.  Many online periodicals and blogs do not.  Many publications are run by profit-driven management whose business model relies on serving ads rather than serving informative articles.  Sometimes you’ll get turned away no matter what you can offer by way of timely data, scoops, or exclusives simply because you refuse to become an advertising partner.

We ran across a situation where a prominent blog started speaking to us about publishing a story and that same day someone from their sales department called us wanting to sell ad space.  If you have the cash and don’t find this contradicting your morals, go for it.  In fact, you might be able to start by contacting the blogs about advertising opportunities.  We chose not to as this would contradict our mantra of ‘our reputation is our greatest asset’.  Not surprisingly, the communication with this publication dried up immediately after we made this decision.

Pitches That Stand Out

Reporters hate being treated like mules for distributing your startup news.  They have egos and principles.  They are humans, not newswires for hire.  We’ve found that the following tactics work:

  • Keep pitches short and informal. Add a picture of an ascii pterodactyl if it’s comical and relevant.  A pitch should start a conversation, not spell out the entire story.
  • Pitch yourself as a resource.  “Fathers Day is coming up.  We’re a cool dating site.  Is there any data you wanted to reference that we could help gather?”
  • Ask for advice.  “We just launched a dating site and you’ve written so many articles about dating. Could I show you the site over coffee and get your feedback?” Even if they don’t write about you, they’ll refer you to three other reporters who might.
  • Show that you are adding value to them rather than asking them to provide you with free advertisement.
  • Build a relationship. Writers are people, not robots eager to disseminate any information you feed them.  Continue to offer them value beyond just pitches and they will become invaluable long-term spokespeople for you regardless of which company you are with.

This article originally appeared on under30ceo.com. To see it in its original format, click here.

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The Innovator’s Guide To Fearless Decision-Making

Making decisions is never easy. Decisions inevitably have to be made based on imperfect information, especially the toughest decisions. One wrong decision is sometimes enough to kill a start-up.

Here are 7 keys to bold decision-making from Katherine Von Jan (Founder & CEO, RadMatter):

  1. Seek diverse advice – Be honest that you are in exploration mode, and talk to every kind of stakeholder related to your quest. Customers, users, subject matter experts, investors, successful entrepreneurs, failed entrepreneurs, authors, journalists, bartenders. Ask and listen, and always give them something appropriate in return.
  2. Find the patterns in the fodder – Take your ego out of it, and let the most important threads emerge. Do it alone, do it with others. Just don’t try to find answers – because you still might not be asking the right question. Notice what is there.
  3. Frame the question – Figure out exactly what you need to know, and what the implications are. What would you do if you had the answer to the question? (Is it worth answering this at all?) Test this with your team.
  4. Ask experts for a reality check – Figure out who the top 3 people are you’d like to have answer the question. If you can’t get those people, try finding others with a similar DNA. Share your question, the implications, and any of the answers that seemed to emerge already.
  5. Trust your gut – You know the answer even if you don’t want to admit it. Write down your decision as if it doesn’t matter. (It’s like hitting save instead of send on that email you wrote in haste.)
  6. Practice communicating your decision. Imagine you are talking to your customers and your team – your ultimate stakeholders. Share your decision in 50 emotions. Say it with sadness, joy, fear, anger, delight… Does it feel authentic? Say it so many ways, that the only thing you feel at the end is confident that no matter how you say it, it’s right.
  7. Implement your decision – Own your success and your failure. Don’t be afraid to make a mistake, because the only mistake you can make is not actually making a decision.

To see the article in its entirety, click here: The Innovator’s Guide To Fearless Decision-Making

This article was originally published on Women 2.0

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7 Tips for Bootstrapping Your Startup

boot image

Here’s a great post from mashable.com about the basics of bootstrapping:

Most entrepreneurs dream of taking an idea and turning it into a successful company, but that takes time and capital investment. Most startups don’t get funded by venture capital or angel investors; the money often comes from your savings, credit cards or friends. Because initial cash flow may be tight, you need to keep your budget realistic in order to stretch every dollar. That’s where bootstrapping comes in.

Bootstrapping means starting a company with little or no money, but utilizing the resources readily available to you. This means keeping your budget low, not taking a salary, working with your team to develop your product for sweat equity or outsourcing some functions altogether. It may take you longer to get your product to market because you are relying on yourself for everything, and often learning as you go. It is, however, a way to keep developing your startup concept.

There are plenty of startups that have been successful without taking outside capital. 37Signals has profiles on a few of them. Campaign Monitor was able to bootstrap because the founders had the background necessary to build and design the product. They also used the profits from their consulting business to fund the project. When Admoda started, they set out to bootstrap from the start, avoid the need for investment, make a lot of money and have fun. The founders put up the original investment and then reinvested the profits to avoid taking outside capital.

How can you learn from those examples and get your bootstrapped startup on the right path? These strategies can get you started.

1. Test the Market

Before you spend money on anything, you should talk to potential customers about their level of interest in your product. Ask them how they would use it, what features they might like to see and how much they would consider paying for it.

This will help validate your model and justify spending the time and money to build your company. It will also help determine which functionality you need immediately, versus what can wait until you gain more traction.

2. Efficiency

Marketing Image

To bootstrap, you need to be as efficient as possible. That could mean doing small, inexpensive marketing tests until you find the best results. When designing your website, first add the most important functionality in order to get a product to market, but to minimize your later work, make sure to consider additional features.

3. Keep the Team Small

A large team could drain your cash more quickly than any other expense in your budget. Until you have a positive cash flow, only hire people you absolutely need. If necessary, give current team members multiple job functions, and offer stock option incentives instead of cash.

4. Interns

Using interns at your startup is a win/win for both parties. The intern gains valuable experience working at a startup and you get support at little to no cost. Since the team is small, the intern might have more influence than they would at a larger company, becoming involved in many aspects of the business.

For your startup, interns provide free or inexpensive labor that leads to quicker profitability.

5. Marketing

Business News Tablet Image

Hiring a PR firm can be very expensive, and there is no guarantee that they are going to get you featured in a magazine or blog. Try outsourcing your press releases, but contact reporters on your own. Find stories and outlets that are related to your project and come up with a simple pitch for a story idea.

Use the free service MediaSync to get a reporter’s email address and contact him or her directly. Reporters are interested in hearing from the CEO of a company, and if you have a good story idea, they will respond. Help a Reporter is another site worth mentioning — reporters search for experts like you to quote in their stories. It never hurts to make yourself available.

6. Outsourcing

If you don’t have the capital to hire an employee on a short-term project, consider outsourcing the work. You can easily outsource your web design and programming, but you will need to weigh the pros and cons of not having that person on-site.

Some websites that can help in your search for off-site talent include Elance and Freelancer. On these sites you can either post your project and have people bid on it, or you can search through the talent and contact potential candidates directly.

7. Social Networks

Use Facebook and Twitter to connect with your customers. Both are free networks that you can use to promote your business to a broad audience. Become the expert in your field and blog on your website or other sites related to your industry. This will keep customers coming back often, meaning higher potential for sales.


Bootstrapping your company can be a rewarding and beneficial experience. It demonstrates how you can accomplish a lot with a small amount of capital. Once you have proven your product in the market, you may need to take on outside capital to help with the growth period. But continue to manage your growing budget as if you’re still bootstrapping; it will help you keep costs down and stretch your money toward success.

Bill Clark is the CEO of MicroAngel Capital Partners, a venture firm that gives more investors access to alternative investments. He also gives investors the ability to invest in startups online through crowdfunding. You can follow him on Twitter @austinbillc.

To see the original post, click this link: 7 Tips for Bootstrapping Your Startup

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Are Entrepreneurs Born or Made?

Psychology has long pondered whether people are a product of their environment and life experiences (nurture) or the result of their genetic make up (nature). There are differing opinions among experts and different schools of thought have dominated at different times throughout history.

There’s strong evidence that the environment around a child all the way through the adolescent years plays a major role in the child’s personality, and by extension, the likelihood of that child entering any given profession. If a child has several fire truck toys, reads books where firefighters are the main heroes, dresses as a firefighter for Halloween, and has a fire truck bed frame, the child will have an early predisposition toward becoming a firefighter later in life. If the parents encourage, rather than squash this enthusiasm for firefighters, there’s a descent chance the child may grow up to be a firefighter; especially if he/she has real life role models who are in the profession, such as the parents friends.

Similarly, a child who is regularly encouraged to solve problems and answer questions, rather than given the answers, will develop the critical reasoning skills necessary to become a leader and an entrepreneur. A promising young entrepreneur will, at minimum, display 3 of several key qualities. First, the child notices inadequacies in the surrounding environment and questions them, rather than accepting them. Second, the child shows motivation and determination to resolve or fix the observed inadequacies. Third, the child is resourceful. These skills can be nurtured by parents, teachers, peers, or others that the child interacts with on a regular basis. As Cameron Herald points out, academic curriculum and attitudes in school can go a long way toward creating future entrepreneurs. At a young age, especially between 8 and 12, the books a child reads can help develop an entrepreneurial mindset. As a parent seeking to encourage entrepreurism in a child, two of the best things you can do are introduce the child to adult entrepreneurs that the child can use as role models, and frequently ask the child how to solve problems that arise in daily life. Here’s more info on teaching your kids to be an entrepreneur. Perhaps the biggest piece of evidence that the a child’s environment influences his/her likelihood of becoming a future entrepreneur is that growing up with a parent in the house who is an entrepreneur, significantly increases the chance of the child becoming an entrepreneur.

The problem with the last piece of evidence is that having a parent who is an entrepreneur, may imply a genetic predisposition for a child to become an entrepreneur. That’s how complicated the nature vs. nurture debate can be. A lot of the evidence could be used for either side of the argument. The idea that children follow in their parents footsteps isn’t unique to entrepreneurs. Famous investor Warren Buffet’s father was a stockbroker. Angelina Jolie, Charlie Sheen, Michael Douglas and others all followed in their parents footsteps as actors. In addition, countless doctors, lawyers, jewelers, carpenters, longshoremen, and others follow in their parents footsteps. It makes sense that if a parent is very good at a sport (or a profession) there’s a genetic predisposition toward that activity and that the genetics will be passed on to the next generation.

In short, there’s no easy way to tell if a child’s future as an entrepreneur is due to nature or nurture, but growing up with entrepreneurial parents in an environment that encourages and champions entrepreneurial activity and thinking creates a very strong predisposition for a child to become an entrepreneur.

Here’s another Ted Talk about the current state of the education system and how it relates to entrepreneurship. Click Here
Keep an eye out for VentureStart’s new domian coming soon.

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Entrepreneurs Start Young

Entrepreneurs often start young, very young. Many future entrepreneurs start small businesses as children. Some examples include, a snow removal business, a lemonade stand, or a used video game company, among others. Cameron Herald, CEO of 1-800-GOT-JUNK and founder of BackPocket COO started several businesses as a child. He went on to become a very successful entrepreneur and gave a Ted Talk 2 years ago about the need to encourage entrepreneurism in children, rather than stifle it. There are certain character traits that Herald believes help predict the likelihood a child will or could potentially become an entrepreneur, and rather than try to fit a square peg into a round hole, Herald suggests schools and parents should encourage those characteristics. He’s largely right. If the American education system (and others) encouraged entrepreneurism from a young age and recognized it as career path in the same way as law or finance, the country would be much more innovative. In addition, small businesses (including start-ups) comprise more than 50% of non-farm US GDP. A strong pipeline of young entrepreneurs could help boost that number and US GDP significantly.

All this talk about young entrepreneurs leads to the classic psychological question, is it nature or nurture. Herold is suggesting that nurture, the experiences the child has, plays a major role in that child’s likelihood of becoming an entrepreneur in the future. We’ll discuss nature vs. nurture for entrepreneurs later this week.

Until then, with Cameron Herald’s  Ted Talk

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