TK: What's To Come

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Week Four, Five... It starts to blur

Oops. Jeremy was right. Stop journaling, and before you know it, you've let it slide. 

Like most everyone else, it seems, I'm still dealing with the roller coaster emotions of starting something, fearing failure but trying not to care too much, wanting to hurry to get something up and running, then dealing with the reality that everything takes much longer than it should.

I've had some great highs: another meeting with my mentor a week and a half ago, a group GSD session the following Friday after our startup visit, and a "running" networking opportunity with the founder of a running brand that I respect greatly, as well as the founder of a nonprofit with running connections. 

And then the lows: never enough time. The usual pattern is that I leave one of these meetings on a high and feeling all fired up, then I go off on my own and get bogged down in some details, or impatient over the dozens of small tasks that need to take place to turn vision into an executed plan. So I need to ask myself at the end of each week: Has there been progress over the previous week? If so, what?

So for the last week, I can say definitely yes. Grit Mode is in live beta, a rudimentary logo is up, I'm putting up bits of content, getting the name out there, rebooting my social media presence, and have scheduled a web design meeting for this week. 

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Week Three: Ideas, Ads and a Kick in the Pants

Lots of learning and inspiration again. The week started off on a good note last Sunday when I watched Bill Gross's IdeaLab IdeaDay presentation, which really resonated with me in several ways. First, the outline on how ideas are generated, evaluated and ranked was very clear and straightforward. Second, the concept of funding "stage gates" provided a couple of useful criteria for how to spend money. Finally, listening to the ten ideas offered to the audience, I was surprised by my own reactions to some of the ideas. I like to think of myself as creative and open to innovation, but I found myself reacting like the naysayers mentioned throughout "The Myths of Innovation," thinking, "oh, no, that would never work" about a number of the ideas, and coming up with reasons why certain ideas were doomed to fail. At the same time, I was also really impressed and humbled by the generosity displayed in Gross's offering up of ideas, and his commitment to improving the world through sharing and helping.

On Monday, we had two guest speakers from opposite ends of the media spectrum: Julia of Watershed Post, a bootstrapping, barely breaking even hyperlocal news site for the economically struggling Catskills area, and Santiago of Monocle, an impossibly well-funded glossy publication catering to the global 1%. I wouldn't have imagined that these two media outlets would have much in common, but they did in terms of how they exert control over their advertisers. Julia does so by creating simple ads for her advertisers, rather than offering to accept whatever they might send her, and she follows up with them to ask if the ads are working. Similarly, Monocle, to preserve the high standards of its brand, vets its advertisers and works with them to create ad content that matches the Monocle aesthetic, and even developing product collaborations with . These examples made me think more about the possibilities for working with advertisers and brands not only to generate revenue for my business, but also to provide a service that creates value for others.

The week ended on a high note. It was Valentine's Day and we visited Kickstarter, and there was chocolate. I can't go into details but their new space in Greenpoint was unbelievable, and to think that this was built from the crowdfunding, sharing and helping impulse... That was very exciting.

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Week Two: Methodology to the Madness

I walked into this week expecting another round of the ups and downs and roller-coaster rides of startup emotion. But then, prepared for the unpredictable, I found myself less fazed by the doubts and uncertainties that shook me up in the early days. So this is the new normal.

  Methodology was a focal point of the week: How to pitch and raise lots of money, how to find the people you need and how to manage your follow-up swith them, how to conduct market research with questionnaires, how to organize your email, how to apply scientific methodology to business problems. The focus on problem solving makes it feel like everything can be managed, every issue broken down into sub-issues and sub-sub-issues until all that is left is a series of to-do lists.

  All of this provided a fitting build-up to my first meeting with my mentor on Friday afternoon. The highlight of my week was getting critical advice on how to structure my product plan in a reasonable, and rather scientific, manner. Left to my own devices, I know I’d be trying to do way too many things at once or in too short a period of time, while probably overlooking some key matters that need to be addressed along the way, with resulting frustration. With my mentor’s guidance, I now have a good outline for planning, a key list of the broad deliverables with dates attached, and a schedule for future meetings. 

[tksky-blog]

Week One: Marriage or Speed-Dating?

This week the real learning began, and it was tumultuous.

There was the excitement of scheduling meetings, discussing ideas and watching them evolve, going places and doing things. Then there was the uncertainty, self-doubt, and the sense that things are changing even if I don’t want them to.

 That’s when the community of our class helps a ton. During our pitching/intro session in our first class with Jeff J. on Monday afternoon, I learned that I’m not the only one that’s shifting about. We are all, in some way or other, “crossing the river by feeling for stones,” to quote the Chinese reform-era phrasing of Deng Xiaoping.

On Wednesday, my feelings were confirmed some more when Jeff Mignon told us that it’s important for an entrepreneur to manage their own expectations and morale, because there will be many, many, many ups and downs. We need all the perseverance and optimism we can muster to innovate.

Jeff J. told us to be prepared for wildly contradictory advice. We should love our projects with a passion that will sustain us for 10 years and that can be communicated to our consumers and investors, yet we should be wary of falling so far in love with our ideas that we are unable to discard the ones that are failing. Are we getting married or just speed-dating here? 

Either way, Jeff J. says, you are boss of your business, and have to decide what to do. But you also have to listen to your customers, and provide a service to them, not just an ego-driven vision of what you think is best for the world.

 It’s exciting to develop these new ways of thinking, figuring out not only what I want my business to look like but how to deal with the contradictory advice and impulses, learning to think in different ways, putting the business model together and doing the market research and competitive analysis—all new concepts to me. Brandon Diamond likened the process of creating a business to going backpacking for a year, in that not only will you learn from the experience but you’ll learn so much about yourself, that it can only be a positive thing. 

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Orientation Week

Lessons learned:

Sponsored content/branded content/native advertising: Whatever we call it, it's how new media companies see the future of revenue and profitability for the journalism business. And there are different ways to get there. Models include creating a platform for writers to connect to companies to create content (Contently), assigning sponsored themes to a features team that sits in the news department (Mashable), or enforcing a total separation between news and business (Buzzfeed).

Mobile and personalization are really important too. From the Buzzfeed visit: "Mobile first, not desktop. Social first, not search."

Awful things on the Internet (slideshows, clickbait viral headlines) don't just annoy me, they're unsustainable, because the platforms relied on to generate traffic, such as Google or Facebook, can easily change the rules to put the perpetrators out of business. Plus, you're alienating your users. And we need users to champion our ventures. 

Agreed upon everywhere: hard news doesn't have to abide by the same metrics as cats. Traction and traffic are very different things (Ben Smith). Still, analytics are extremely critical to understanding everything everyone does online and it seems most of the companies we visited are creating their own tools for data analysis. 

When it comes to fundraising, more than one entrepreneur emphasized looking at actual cash needs rather than trying to raise too much too soon. Stick with what's necessary, build something and get it out there, and start getting into the feedback loop that will improve the end product. Another founder explained the tradeoffs between raising a lot of money and the constraints on exit strategies. Angels and VCs expect such a large return on their investment that it can limit a company's flexibility in some ways, forcing the founders to think bigger by necessity. Companies such as Mashable and Muckrack have gotten pretty far with minimal outside investment. 

Ask for advice first, not money. In the early days when you need money it's best to have a pre-existing relationship with the people who will back you. And make a spreadsheet of all the people you want to talk to and start looking for ways to make connections, whether through other contacts, research on LinkedIn, or plain old cold-emailing. Build a stable of advisors, who should not be looking for a chunk of your company off the bat.

Some of our experiences confirmed some of my hunches about what I want to do. The example of The Dodo, a RebelMouse community focused on animal stories, shows how niche media can be championed by some of the top people in the business and get significant financial backing and press attention. (Of course, it helps to have a Ken Lerer behind a venture.) VCs will look for incredible growth prospects and/or a passionate group of users that is hyper-engaged. 

Samuel Beckett inadvertently wrote the motto of the startup/entrepreneurial spirit: "Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better." Keep learning and find your own path. Most ideas don't work out, some business models have to go through multiple iterations, and some companies spend thousands a year to renew domain names that will never see the light of content. 

Common sense about human relations: Resolve people tensions quickly, talk in person and avoid email wars, and watch what you say because everyone talks and gossips. 

Competition is verification that you're on the right path. (Paul Berry)

You are better at almost anything than you think you are. (Contently)

My fellow fellows are amazing. I've decided my long-term goal is to become an angel investor so that I can fund great people and ideas like theirs. To get there, though, I'm going to have to make a successful business first.