An Exercise in Startup Ambition: What's your ask of Obama?

Given that he doesn't have much to do these days, Barack Obama goes poking around Crunchbase one day and he stumbles upon your startup.  He finds your company, and obviously being super impressed, he reaches out and asks you what he can do to help.

What do you ask of him?  (Or anyone else on that level...)

This isn't an easy answer.  The truth is, you're probably not ready to handle whatever the former leader of the free world can do for you, but you're obviously not going to let this opportunity go, right?  You have to come up with something.

This is a problem of multiple dimensions:

First off, you have to narrow the scope of possibilities.  This is hard.  Obama could probably do just about *anything* for you, but you have to pick one or two concrete things.  You can't be like, "I don't know, what were you thinking?"  He doesn't know anything about startups and you're lucky he even thought of you at all.  You're going to now throw it back to him to plan out what he might do for you?  No, you have to make an ask.

Second, anything you come up with is barely going to register for him in terms of level of impact, but it's going to be more then game changing for you--it's going to feel ridiculous.

Maybe your company is seed funded, or has some friends and family, or is barely more than a Powerpoint.  Even if you have your Series A, the scale that you're operating on probably doesn't even come close to what he's been thinking about these days.  He's on the "ending malaria/making sure every woman in the world gets equal pay" kind of level", and you're out there building an app with three devs, some cheese dip and an office dog.  Even if you have a worthwhile mission, you're going to have to get over the fact that anything that he could come up with that he'd pay attention to is going to feel crazy to even ask of him. 

But this is how you make a leap as a startup.  

One of the easiest things you can ask of something like that is to invest.  Investing insures that someone is always part of your company.  It gives you an excuse to e-mail them and your updates keep you top of mind for them.  It gives you an excuse to ask for more later.  Getting someone to invest in your next round is like getting to wish for more wishes and having it granted.

Get over whether you know if this person invests or not or what size check they can write.  Any person who gets to this level of success could probably write at least a $10k check or maybe more than you think.  Remember that you're not asking for their money--you're providing them with a great opportunity for them to trade their wealth for interestingness.  This is something they do all the time in a variety of ways.  

Advisory boards are also a great way to rope people in that you probably have no business getting on boards.  The key is to make them about something bigger than just your company.  If you're a financial startup, make them about financial empowerment.  If you're a fashion company, make it about style trends.  If you're a consumer product, make it about world class customer experience, etc.  

It's really easy to be focused on short term goals as a founder--getting to that next raise, making that next hire, or just making sure your bills are paid.  The companies that make huge leaps in impact and value execute these kinds of headline making moves, leaving their competition far behind in the rear view mirror.  Knowing what these moves could even be is hard, and it's probably something worth talking to your investors or thought partners about, and definitely something to plan around.  This comes into play so many times.  People you know will say, "Hey, I know the former CEO of X and she's retiring and looking for something to do."  

Don't let those opportunities pass you by.

Find Success by Helping a Mom Find Success in Your Company

A few years ago, a friend of mine got hired by a company as a software developer.  She was an early riser and liked to get into the office around 8AM.  A diligent worker, she was super focused from the moment she sat down at her desk--and so by the time 6PM came around, she had gotten a lot of work done and ready to call it a day.  

Her young male colleagues had a different approach.  They strolled in at around 10 or 11AM, and didn't really get going for real until about noon.  They spent a lot of time distracting themselves, but worked deep into the night--doing the same amount of work as she did, but stretching it out until 10 or 11 at night.  

Because my friend would take off "early", she got a reputation for not working as hard as everyone else, even though the results said otherwise.  Eventually, they let her go.  

What struct me about this situation was that it was a culture that obviously couldn't scale past young, single people.  I thought, "Wow, there's no possible way anyone with a kid can ever work at this company."  

As I spoke with Adam Milligan about in the Startup Recruiting Podcast, tech companies are idea factories--and they win by bringing the best ideas to light.  That means that successful environments are ones that foster a diversity of perspectives, support great communication, and favor quality of solutions over the speed and hours of simply "typing" the code.

That's why a great barometer of your potential for success can be found in how ready your company is to support a mom (or a dad, of course) returning to the workforce after taking time off for family.  If your hiring process really does favor the people who can bring the best ideas to the table, statistically speaking you should have a lot of moms in that process, particularly when they're often your biggest customers.  The question is, can they find success in your environment, and what might hold them back.

That's where efforts like Path Forward come into play.  Path Forward is a nonprofit organization on a mission to empower people to restart their careers after time spent focused on caregiving--not just moms raising a kid, but all sorts of family situations. They fulfill this mission by working with companies to create midcareer internships — sometimes called “returnships” — to give women (and men) a jump start back to the paid workforce.

I interviewed Path Forward's founder, Tami Forman, on the Startup Recruiting Podcast (or here at Soundcloud, in case iTunes hasn't updated yet) to talk about companies can go about making their environments supportive of this transition and how the companies involved in the program have tapped this underutilized talent pool.  (Over 80% of the participants in their program wind up getting hired by the companies that they intern at.)

I'm a big believer that companies should rethink their purpose in order to achieve sustainable success.  What if the goal wasn't to create shareholder value, but to create the best place for the most talented team (not just individual people) to work?  Remember, teams are more than the sum of their parts.  Wouldn't product and sales success flow naturally from that?  So why not focus on it as a priority?  Seems to me that's something that should be done from day one, not just when you get around to hiring your first Head of People.  

What I Say When a Founder Asks for Feedback

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A Story About Fear, Shame, Expectations and Money: My Investment in The Financial Gym

Today, I can finally announce Brooklyn Bridge Ventures' investment in The Financial Gym's $1.8mm seed round, which I led, alongside Alpine Meridian, Secocha Ventures and several high ranking execs from the finance world.

What's the Financial Gym?

It's a membership based space and service where you can work with a Certified Financial Trainer 1:1 to get financially healthy.  

What's the Financial Gym?

This is the Financial Gym...

The Financial Gym is the culmination of founder Shannon McLay's desire to eliminate the "fear and shame" that comes with financial difficulty--something people are facing more than ever before.  Two-thirds of people in the US have no more than just a few hundred dollars in savingsSeven in ten college grads finish with an average of $40,000 in debt, adding up to a record high $1.4 trillion dollars in total--a 150% jump in the last decade.  And wages?  Wages have grown 0.2% annually since the 1970's, lagging inflation.  Each new generation is forced to do more, with less, despite startlingly low levels of financial literacy--only a quarter of millennials can demonstrate a basic understanding of personal financial concepts.  People are graduating with sky high expectations of themselves and what they can do in the world, but no one ever bothered to teach them how to manage a shrinking checking account in a world of low pay, suffocating debt and high costs.  

Apps might work for the most disciplined and well off people--but the moment you have to make hard decisions about selling things to downsize, when you want to talk about a purchase, or when you need some extra accountability to stay on track you'll fall right off of them.  Anyone who has ever had a personal trainer give you a 6AM wake up call or who has gotten grief for missing your regular Soul Cycle class knows you can't cheat a human coach.  

Membership provides you planning meetings, follow ups, regular check-ins, as well as events at their beautiful new space in Flatiron (with more locations to come, obviously!).  There's no downside to scheduling a free 15 minute warm-up call to learn more.  

What I also want to add into this story is a little bit about expectations.  I don't think I've ever met a founder who has more expectations of themselves than Shannon.  Sure, we have a financial plan, but Shannon's got a whisper number of her own that she's managing to herself that I'm sure is an order of magnitude greater than the plan we set out.  Much of our interaction is around making sure not every move she makes at the Financial Gym is going to go right--even though she's proving me wrong so far.  :)  Her bio reads that she runs "the world’s greatest financial services company" and I honestly think it's true--or it will be when the Gym is in every city across the country.  I don't think there's a single company in the finance space whose customers have the same kind of positive emotion towards a company as members of The Financial Gym.  

She also faced a ton of expectations during this fundraising.  Other investors wanted her to be anything other than what she was.  They told her to play down the brick and mortar in her pitch.  They said she should be an app.  They said she should be a bot.  

People have asked me how I've come to fund 20 female founders and counting, and I think I realized after meeting with Shannon what gets in the way--expectations.  I can think of countless deals that I got to a yes only after asking the question, "What do you really need to raise?" or "Are these numbers really as far as you think you can take this company?"  

I asked her if building physical spaces was really important to her and she said it was--so I asked why it was so played down in her deck.  When she said that it wasn't what investors wanted to see I just told her she wasn't pitching the right investors--that if she really wanted to build a brick and mortar company, she should just own that and find people who see her vision.  She fixed the deck to include her plan for multi-location, multi-city world domination with Financial Gyms everywhere and I responded with a term sheet.  

So I'll end this story with a motto the Financial Gym uses with its clients:

"What are you working for?"

If you want to get funding, I think your best chance is if the answer isn't "VCs".  

The Atomic Element of Your Marketing

In the last couple of weeks, I've had two similar conversations with my portfolio companies.  They were just starting to build out their marketing strategy and they were faced with the challenge of how to staff it.  Do you hire someone senior who might feel like the execution of the work was beneath them--or who simply hadn't done it in a while?  Or, do you hire someone adept at the actual creation piece, but who needed guidance around how things were strategically put together at a high level?

We had opted to create the high level strategy as a board--since no one knew the companies and their customers better than those that created it and invested in it.  What we realized was that we were in a search for consistency.  What would be the common thread across all of these available channels?

What we needed was an atomic element of our marketing.  What was it that we actually wanted our marketing to do or to show?  Do we inspire?  Do we tell stories?  Do we help?  Do we show off?  Are we all about people?

If we're about people, than people need to be in every single piece of marketing collateral that we create.  If we tell stories, than everything you see from us--from the TV ads to our packaging to our Instagram posts, will be stories, because that's what we do.  

Once you figure out your atomic element, it becomes a lot easier to fit your brand message into various channels, because you know the vessel of delivery--the atomic element of your marketing.