Lovelletters: Startup Chess and the Zen of Ordering

[Editor's Note: The latest installment of Lovelletters, GeekWire's startup advice column, features an exchange between Rebecca and Jenni Hogan, the KIRO-TV personality behind the website Mission Hot Mama.]

Dear Lovelletters,

I just launched my website – MissionHotMama– and it’s going better than I could have dreamed. Opportunities are everywhere to grow, build the team, and monetize. There are different kinds of financial offers coming in, from sponsorships to funding plus even potential partnerships that could really benefit the community that supports me. I want to make sure I embrace this momentum and make smart decisions. I’d love to know your opinion on what to focus on and when?


Dear HotMama,

Thanks for your Lovelletter!  I’m a big fan of Socrates, and am also of Jewish descent, so in those grand traditions, I’d like to answer your question with a question (or three).

  • Who is your customer — tell me about their “psychographic” (what they want and need) as well as demographic.
  • How will you know that you’ve succeeded in your mission (what are the metrics of success in terms of your customer experience, and your business goals)?
  • What is your threshhold in terms of prioritizing these goals? For many, it’s a tolerance for ramen noodles and couch-surfing, for others, it’s about opportunity cost of your capital, but everyone has a limit. What matters most to you, now? Pageviews, engagement, profitability, breadth, depth?

In the meantime, I’ll leave you with this:

  • People are like fish. We can be easily distracted by shiny objects.
  • A throwback to a Startup Day talk from Ben Huh a couple years ago: as a new entrepreneur, you can’t be big and focus.  So as you zoom in on all these opportunities, use the lens of your end-game: does this (seemingly incremental) decision support my ultimate goal?  Be a broken record– keep asking yourself that question.
  • Ordering matters. Quoting Steve Harris (ThinkAutomatic) in a chess analogy, even if you know what the end-goal is (check-mate), and where your pieces need to end up on the board, the order in which you move them can determine whether or not they’ll ever get there.   These decisions have both short- and long-term impact, and include whom you hire, with whom you partner, the content on your site, and ultimately, exit scenarios.

Lovelletters


Dear Lovelletters,

Thanks! Here is my stab at answering those questions:

  • MissionHotMama is dedicated to impacting women in a positive way through social media.
  • Our customer is the reader. They’re working mothers (or soon to be mothers), who enjoy striving for the best in life and are online savvy.
  • They’re busy and do things with a purpose but love knowing their actions help other people.

To succeed in our mission we want to inspire them to spend time on themselves because if they feel great and kick booty in life then the people they do things for will benefit even more. We measure this by their interaction on the site, response to our calls to action, and their passion in spreading our mission to friends. My top goal is that I want to see them engaged in the site in a meaningful way, and use every social media channel to drive that goal. I’ve got a key hire in mind, am intrigued by growth opportunities, and want to make sure I sustain this business.

HM


Dear HotMama,

This context is really helpful!  I think your brand statement — which may continue to evolve — might need one more element:  you’re all about helping these mamas become the stars of their own lives.  Given your target market, think about ways you can reward what they care about (helping others).  You want impact, not just impressions. I love that you’re “dogfooding” it (you’re your own target market)– so at the end of the day, make sure you keep your eye on customer satisfaction as you’re putting things in order on the business side.

Now about that housekeeping:

  1. Get your corporate entity established, work through your “cap table” (i.e., capitalization, who owns what today, who will own what in the future, what is the business worth now). I’m not a lawyer, don’t play one on TV, but can send you to some folks who are trusted counsel. I’m putting this one first on the list as it’s cheaper to get it done right (now) than pay someone to unravel this later.
  2. Bring in a player who’s got skin in the game (some equity) and will eat what they kill (commission).   Get that cap table piece straight before slicing up the equity pie; this hire is second in line, but on the heels of step one.
  3. Hire folks who are core to your value proposition and carrying out your mission, go outside for some adult supervision (legal, accounting), and think about having some advisors or consultants teach you how to fish (in your case, with some specific social media channels), so you can empower your hot mamas to fish (read: execute) moving forward!  That key hire should be part of partnership discussions, so put her to work on this third step, stat.
  4. Keep killing it while bootstrapping. Fundraising will take time, so as you’re getting your ducks in a row there, set yourself up to hit those business milestones we discussed offline.  This will make the company much more attractive to investment, and frankly, command a higher valuation for you in the market.  The most successful companies that I know who’ve gotten funding do so because they can bootstrap, not because they can’t.

You’ve got some really interesting opportunities, some which could benefit from expansion capital, some of which provide that capital, but as you get your house in order, I know you’ll stay true to your mission!

xoxo Lovelletters

Rebecca Lovell, GeekWire’s chief business officer, is the former executive director of the Northwest Entrepreneur Network, teaches a class on Venture Capital in the UW Foster MBA program, and is also serving as a mentor for TechStars and a community advisor for Startup Weekend.  Submit your lovelletter to rebecca@geekwire.com. She can be found in cafes and karaoke bars near you, and is always happy to talk shop with startups.

  • http://twitter.com/jennihogan Jenni Hogan

    Thanks so much for your advice!! Cheers to helping mamas dream big xo I can’t wait to share chapter #2 with you. 

    • Anonymous

      Thank you, Jenni! Very much looking forward to the next installment from the Chief Hot Mama. ;)

    • Anonymous

      Thank you, Jenni! Very much looking forward to the next installment from the Chief Hot Mama. ;)

  • http://twitter.com/bestgeekfriend Matt Ebert

    Love the advice Rebecca, you rock :)

    -Jenni’s Chief Geek Officer

    • Anonymous

      LOVE the title, Matt!  Thanks for reading and the props.  :)

  • Deb Hagen-Lukens

    I love this concept, Rebecca! Great advice, naturally. Good luck, Jenni! I know this business is near and dear to your heart.