The Toolshed

A place for visioning, tinkering, and building around the topics of education reform, technology, and female entrepreneurship.

Musings on Entrepreneurship.

If I could distill my main learnings over the past nine months down to three things, it would be:

  1. Ask for a lot of advice, but understand that someone’s opinion is just one data point.  I’ve spent a lot of time setting up coffees and calls with fellow entrepreneurs and investors over the last year, seeking their advice and perspective.  (Incidentally, I’ve also received a healthy amount of unsolicited advice from folks that run the gamut from well-intentioned to self-aggrandizing.)  I’ve learned a lot through these interactions, and I think I’ve dodged a number of bullets and/or been able to get ahead of some of the questions and challenges that are coming down the pike.  And one enormous ancillary benefit has been gaining confidence in pitching my business and presenting myself as an entrepreneur.  Having the opportunity to talk about Fizz in a low-stakes environment has strengthened my skill at pitching Fizz in higher-intensity moments–it’s helped me smooth out the narrative and even the jargon I used to frame my undertaking.  And observing how other entrepreneurs talk about their work has also refined my approach–whether it’s seeing how I don’t want to be perceived or how I do.  But what’s struck me most about this concerted effort to learn as much as I can from folks further along than I?  It’s that there are literally no right answers in entrepreneurship.  I’ve even had entrepreneurs tell me completely opposed viewpoints–entrepreneur A says that SEO/SEM doesn’t matter in the short term and to put all our energy into direct sales; entrepreneur B says you’ve got to put in the time early on to get your content marketing strategy in place or you’re cooked down the road when you’re running out of money and still scrambling for inbounds.  Entrepreneur A says that there’s no way we’ll raise a seed round with our business model and our traction and Entrepreneur B says he raised his while pre-revenue and without any connections to the Chicago community.  It can be really, really hard not to get whiplash or to feel disheartened in this environment.  But what we’ve come to say, internally, is: “well, that’s one data point.”  And maybe it should be a consolation that there’s such a wide constellation of responses–if the answers were obvious and consistent, we’d feel a little stupid.
  2. Customer servitude, customer servitude, customer servitude.  They purchase, therefore we are.  I was sort of gobsmacked earlier this year when a couple of entrepreneurs were sitting around venting about how “stupid” their customers were.  They were swapping stories along the lines of: “You won’t believe the DUMB ticket I got from customer service” and “These idiots keep trying to use the system in this weird way…”  I was so frustrated–those instances are GIFTS.  You are getting real, live customers who care about your tool to tell you when something isn’t quite right.  Releasing a product is a series of unpleasant encounters with reality–yes, unpleasant because you realize where your hypotheses were wrong and where your estimates fell short and it can be a lot of work to address those gaps.  But at the end of the day we have to understand that we exist to serve a customer and if the customer isn’t clear on how to use your product, that’s your fault.  That’s your job. I’ve also noticed that our customers will often talk about us, as in my co-founder and I, when they’re talking about why they like Fizz.  They’ll say: “I really like working with you guys.”  I don’t mean to be self-promoting, but I sincerely believe that genuine care and attention to the customer will get you ahead, build loyalty, and drive sales.
  3. Customer acquisition is king.  I think we had a leg up on this learning early on because my co-founder has a background in sales operations and really brought a lot of insight into B2B sales right out the gate.  We knew we needed to get Fizz feedback ASAP and that we had to operationalize a sales process that would enable us to validate our market hypotheses STAT.  But, like every entrepreneur, I underestimated the complexity of customer acquisition, and the tremendous amount of time and energy and emotional turmoil it would consume.  An investor recently told us that he thinks a lot of startups fail because they don’t think enough about customer acquisition, and that he looks for an “unfair advantage in customer acquisition” when he’s making an investment.  That’s what we’re after now.  We’ve cultivated an interesting set of insights about which companies to target and why, and we’ve also developed some unique lead sources that I think are putting us on the right path.  Something is working, because we’re seeing big conversions from cold outbound emails to appointments set.  But this piece is so freaking complex.  I sometimes get lost in it myself: which of the market subsugments should we try and for how long?  What marketing message should we send their way?  What pricepoint is right for that individual?  Is the product yet developed enough to meet that stakeholder’s needs?  Etc.  It feels like there can be so many levers to pull, and everyone will give you different advice on which to pull first and why.



The Leaky Pipeline Issue.

The topic of the scarcity of women in technology comes up on a nearly daily basis for me, in forms as wide-ranging as a well-intentioned male acquaintance asking “what it’s like to be a woman in tech” (these conversations are often painfully loaded with awkward assumptions) to a dear friend talking passionately about a gender-freighted experience she or a friend has had in the industry to scouting new talent for my start-up.

Well, the sharp Freada Kapor Klein said it best at a recent demo event I participated in out in Oakland, CA: “It’s not just a pipeline issue.  It’s a leaky pipeline issue.”  It’s not just getting girls into the funnel, it’s keeping them in the funnel for a long time.  (This is a large part of what interests me about Fizz — it’s potential to retain and promote the best talent in a more fair and equitable way.  But that’s a bloglet for another day.  Suffice to say that I have a lot to say on the issue of gender bias in talent management.)

My thoughts on this complex issue evolve over time, but top of mind thoughts for today:

  1.  Invest in girl empowerment programs, including ones focused on STEM education for girls.  (But not exclusively STEM-focused programs.  I would argue that programs focused on nurturing creative confidence + physical fitness can have strong adjacent outcomes that will in turn lead to more women pursuing “typically male” careers.  Maybe this is a hat tip to my educational background in the humanities and my confounding subsequent dedication to the world of technology.  But I digress.)  Nike does a lot of interesting work in this area, but there are also smaller rockstar non-profits and impact businesses addressing this need in different ways.  My friend Annie Warshaw runs a rad company called Mission Propelle that empowers girls through yoga, literacy, and mentorship.  Annie will change the world because she’s insanely talented and bright and approaches her work with so much authenticity and energy.  It’s programs like hers that can widen the funnel to include more girls.
  2. Mentor the women around you.  I have dedicated a lot of time to supporting the women (especially younger ones) in my life.  I am intentional about taking my female interns and colleagues out for coffee/lunch/a drink to talk about professional development + challenges.  Especially with the younger ladies, I am nauseatingly explicit: “Make sure your voice is heard!” “You can do this!” “I expect great things out of you!” And I always share some of the specific tactics I’ve learned.  A lot of it — in my opinion — is becoming aware of when you’re tripping over your own gender and inadvertently conforming to gender norms.  I didn’t even know I was supposed to — or that I could– negotiate my salary until I read Lean In.  No joke.  I read this book and immediately went to my boss at the time and asked for a raise.  I got it.  I also didn’t realize I was often brushing off praise and reattributing my accomplishments to the team.  It was hard to coach myself out of that mindset — and I’m sure an argument can be made that it’s kinda beautiful and rad that most women are inclined to share glory with others — but I trained myself to bite my tongue and say, “Thank you.”  And then there are even more minute tactics I’ve learned — for example, I am typically not the loudest person in the room.  I’d rather listen, take it all in, and then share a well-formed opinion.  I’m more inclined to ask a probing question than to make an aggressive claim.  But you need to make sure your voice is heard or it becomes habit to sit back and let the boys duke it out.  You need your horse in the race.  So there were times earlier in my career when I would head into a male-dominated meeting and tell myself: “You must say something within the first minute.”  It worked.  Once your voice has been heard in the conversation, you’ve set a precedent for participation.  And, at the suggestion of my brilliant aunt, I semi-recently used power poses to counteract a particularly aggressive male I was working with on a frequent basis.  He just took up a ton of space.  I felt trampled over, shut out, silenced.  Power poses changed everything.  Spread out your papers on the desk, put your hands behind your head, put your hands on your hips.  Show that you can take up space, too.
  3. Seek mentorship from the women around you.  I give and take on the mentorship side of things.  While I try to be mindful about nurturing the more junior ladies in my life, I also look for women who can teach me.  I have a monthly mastermind with a fellow female entrepreneur — her support and thoughtful guidance humble me and fuel me, and have bugged many-a-bright-and-more-accomplished woman with requests for advice.  But the point here is: let’s build an ecosystem of women helping women.  My personal opinion is that building out these networks organically is more powerful than participating in a “women in tech” group.  No knock against them — I understand that they work for many.  But in my experience trying to launch an “ed-tech women” group here in Chicago, we all show up and then don’t know what to do.  “OK, we’re here.  Next?”  If you’re instead proactively seeking targeted advice and showing love and support for the women in your professional network, things happen.  Just my two cents.  I also think there’s a kind of weird profiteering that happens in some of these professional networks.  I remember I received some sort of “invite” to be one of the top women in technology in such-and-such female network.  After a lengthy “screening” call, they let me know I’d be billed $1000/year.  What the hell?!  Just, no.
  4. Don’t demonize the men.  Yes, there are horrific stories of outright sexism emerging on the reg.  This is the latest and most stomach-churningly annoying. But let me be real: many (maybe the majority?) of my biggest cheerleaders and strongest mentors have been men.  I’m fortunate to have the tireless encouragement of my father, brother, husband, and brothers-in-law.  They are all convicted in my abilities and dedicated to helping me succeed.  And I’m talking about the Jason Henrichses of the world, wicked smart businessmen who understand that diversity is not just a “good thing” but a necessity in the workplace and who are working to even the playing field in any way they can.  As an example, Jason rounded up some other awesome guys here in Chicago — Ethan Austin at GiveForward and Adam London at Uptake among them — in an informal working group focused on promoting female entrepreneurship.  All three of them took time out of their busy days to encourage me in the early days of co-founding my new start-up, opened up their networks to me, and gave me rock-solid advice.  And there are well-known gents out there making some noise about this issue, like marketing genius Everette Taylor (read about it here). So, it’s insultingly reductive to focus this conversation on what men in the workplace do or do not do.  (Illustrative example being the weird turn this Hacker News thread comparing the pros and cons of being covered by HackerNews vs. TechCrunch vs. ProductHunt took when folks started assaulting Ryan Hoover of ProductHunt for building an elitist, white-male-only “echoing chamber” disguised as a product discovery platform.)

As with all things, an evolution.


Moneythink is a learning-oriented organization.  I can say this with confidence because I have been tasked with and resourced to tackle some pretty big questions, to float solutions, and then to report back on what we’ve learned.  I work hard to ensure that every item on my roadmap is linked to a “what we want to learn” statement; my CEO is wont to ask me to target learnings for various undertakings and pilots; I have a living document called “The Vault” where I chart user insights and problems.

I love this.

Recently, the rest of the senior leadership team huddled up to think about articulating this orientation a bit more sharply.  I had drawn up an organizational snapshot that identified, at every level of the organization, the questions that we are tackling at each layer — the provocations around which we orient our work.  At the highest level, for example, we are asking: How might we build the financial capability of American youth?  We have core solutions we’ve advanced in response to this, and we will be measuring our outcomes against specific goals.  At the tech exec level, I own the provocation: “How might we use technology to drive the long-term financial outcomes we’ve identified for ourselves?”  I have my own solutions to this question.  When I bring my product manager on board, I will have him or her own the question: “HMW drive engagement with the smartphone technology we’ve built?”

I like this strategy because it resonates with perhaps the best bit of advice I’ve picked up this year: “Lead by owning the questions, not the plans.”  How powerful, humbling, and clear is that imperative?  My impression as a younger member of the workforce was that senior leadership was dictating strategy from the top-down.  This model highlights a more empowering model of leadership: we set the questions, we push our staff to answer them with proposed solutions to the best of their abilities, and we measure their efforts.  If things aren’t working, it becomes pretty clear that new solutions are in order.

HCD vs. Mission.

I just enjoyed the most exhilarating and exhausting two-day workshop visioning around the future of our technology solution with our tech partners.  It was exhilarating in that taking a step back to look at the big picture and to dream really big about where we can go reminded me ever more poignantly of the mission I am working toward and how my day-to-day struggles pertain to those big social goals.  It reinvigorated a love of the product we’ve developed, almost made me nostalgic and proud of the amount of thought and effort we’ve put into this solution.  It made me feel unalone in my work on technology strategy, where I can often feel like an island given the small nature of our organization.  (And, to quote John Donne, no man is an island.) It was exhausting in that it required a lot of mental gymnastics, looking at our work across a big canvas and then diving down to study the finest minutiae — which actions should trigger which push notifications and how complex those schemas are (or aren’t) to implement; how we can scale back desired analytics reporting features into an MVP version (i.e., which metrics matter); whether or not the addition of a student’s school beneath his/her name is a valuable addition and the level of visibility different users should have, full-stop.  It was a lot of drilling deep and getting into the weeds, a lot of pulling and sharing of information, a lot of long pauses as we puzzled over potential solutions — and then a lot of sweeping up into Big Dream Talk.

It was all-around awesome.

And yet.  There was a cloying voice in my head that kept asking: “Shouldn’t we have the kids here?  Shouldn’t we be re-starting the process we undertook when we brought in to help us?  Is it OK to vision and build off of what we’ve already built without going back to the source?”

And yet.  We have learned a lot about our students and how they relate to our technology.  We know that there is a direct correlation between number of likes/comments received on a post and overall performance in the app.  We know that they “just want to know someone is listening.”  We know that certain types of classrooms are more optimized for tech adoption.  We know that students often are unable to see themselves as “savers” or as financially empowered because they do not believe they have the resources to do so (and by resources, I literally mean that they do not think that they are financial beings because they do not have enough money).  We know that students spend the majority of their free cash on food purchases and shoe purchases.  We know that they like to “flex” (a term new to me) their cash, to show off the stash of dollars that they have.  (What this suggests is problematic — lack of access to accounts; lack of understanding of security risks; desire to emulate what they’ve seen in pop culture, especially music videos; association of self-worth with cash holdings; etc.)  We know that they love emojis (the vast majority of posts are accompanied by them).  We know that they like points for points’ sake.  We know that they like to unlock surprises.  We know all of this based on tests we’ve run, conversations we’ve had, posts kids have made, and data analysis.  So, I came around to the view that I did have the students’ voices present in the room — just mediated, perhaps, by a lot of thinking and data analysis and reflections.

There was another strain at hand.  There were the clear comments, observations, and insights we’d gleaned (as outlined above) that pointed us in certain feature directions.  And then there were the mission-level, organizational-level hopes we had.  If the end goal is to help students make better financial decisions, there are certain…breaks? disconnects? between making a product that is fun and sticky and making a product that drives and reflects the performance of specific financial behaviors.  And often these things just don’t match up.  Is it OK to test a feature that may be more vitamin than painkiller?  Do we always need to shroud the vitamins in painkillers?  Is it OK to have a high-level, org-level idea informed by best practices in the field and to implement that feature even if users haven’t asked for it?  And, dare I say it, even if users have suggested the opposite?  Let me give you an example: we know that the social nature of our solution was one of the key value propositions for our students.  Time and time again, when asked why they used the app, they would say: “I liked seeing what other people were buying,” “I liked comparing my results to others,” “I liked that someone was listening.”  And we’d also see, in the data, that the more comments and likes they earned, the higher the retention rate.  And we’d notice that the more kids that were posting, the more likely that others were to post.  These are fairly obvious and even expected observations, but they are meaty and not-to-be-ignored, nonetheless.  There is something sticky and powerful and even natural to kids to be sharing information and to seek out and receive affirmation in the form of digital likes.

And yet.  When we’re thinking about our work from a financial outcome perspective, one idea we’d had was to include a “financial meter” modal that might pop up when students log in each week.  They answer three questions: did you save today? (respond to this by tapping a single dollar sign; two dollar signs; or three dollar signs to reflect the relative level of saving); did you spend money today? (again, three dollar sign options to reflect the amount of saving); and how do you feel about your finances? (with three or four possible smiley faces).  We think this would be fascinating in that we could gather aggregate trends about whether or not our kids are saving more and their overall affect around their financial status.  This would be powerful data for us as a program and would have the added benefit of making students feel like the tool is a bit more personal, a way to think about and store financial information about themselves.

And yet.  They haven’t asked for this; in fact, they seem most attracted to sharing moments.  And this would be the opposite.  How do you reconcile the HCD approach, listening carefully to the wants and needs of the user and only building to their specs, vs. a big mission around prevention?  Does HCD only work best when we have a painkiller solution on the table?  What about the vitamins?


My husband works for Groupon and has developed an incredible amount of insight into sales strategy and operations.  They are a truly data-driven company, and the kinds of analysis they’re conducting and the level of data they’re leveraging is astounding.  Drilling a level deeper, he’s constantly bringing home fascinating tidbits around optimized sales tactics — from the time of day, to the length of call, to the tone of voice, to everything in between.  He has even more mind-blowing insight around incentivizing salespeople to hit their targets, motivating a young salesforce, and — in general — being a bad-ass manager.  (He may be the only person I’ve ever met that was a born manager.  He’s a force.)

But one of the most powerful pieces of advice he’s brought home came from one of his managers, who said:

“If you’re doing the same thing at the end of the year that you were doing at the beginning of the year, you’re not doing your job.”

What a powerful charge for personal, professional, and organizational growth.  Our CEO often says: “We want to obsolete ourselves.”  It took me awhile to come around to this phrase: it’s intentionally aggressive and even challenging to digest.  And yet.  For a non-profit trying to solve a big problem, evolution to the point of extinction is the ultimate goal.  Solve the problem not just fully but fundamentally — at the root — and you won’t need to be around anymore.  This, of course, requires a massive vision and confidence in our ability to literally change the fabric of our culture in substantial and meaningful ways.  It may mean mandating financial education; it may mean bringing better, more affordable products and services to the un- and under-banked; it may building pop culture references reflecting greater fiscal responsibility and financial mindfulness.  It probably means all of these things and more.  But at the root of all of this is the assumption that, in order to deliver something powerful, we must continue to evolve and grow and tackle and iterate until the problem is totally eradicated.

Though my husband’s boss was not speaking in terms of our organizational mission, I see the thread that ties here.  And I also see the incredible power in charging your employees to push themselves to grow, to continue to solve new problems and create new efficiencies, to resist the desire to rest on one’s laurels.  In a fast-paced company like Groupon, it’s a problem if your staff aren’t changing given the rate of evolution the organization continues to see.  I love the idea of instilling this sense of expected change and growth up front.  For one thing, it prevents the likelihood that folks will rebel when things change too much or too quickly; they will have been onboarded with the expectation that things will and should and must change.

So – I digressed a bit from my earlier goal of sharing 5 learnings per week.  I may oscillate between one big learning or five smaller ones.  This blog, too, will evolve.

If You’re Not Surprised, It’s Not Useful.

As per my new routine, I’m taking stock of my key learnings from this past week:

1.  “The biggest thing I’ve learned about providing direction is that you do it with your ears and not your mouth.”  This quote comes from Silicon Valley darling Kim Malone Scott, in a great article reflecting on lessons learned from managing people at Apple, Google, Dropbox, Twitter, and Square.  This is tough advice to apply; work is busy, and good managers are efficient.  And listening and altering plans based on what you hear can be time-consuming and occasionally schedule-thwarting.  But she makes great points about how to lead and build a productive, happy workforce.

2.  “If you’re not surprised, it’s not useful.”  I can’t remember where I heard this, but I jotted it down as a good piece of wisdom with regards to testing a product.  (It has “Lean Startup” written all over it, so I’ll chalk it up to one of the brilliant speakers from that event.)  I think the big takeaway here is that, as a product owner, you need to spend your time looking for what’s not working or what’s working out in a way that differs from your expectations, as those are the areas that need your attention.  If all is going to plan, you’re not growing, or your not pushing yourself, or your not measuring the right thing.

3.  “Pitching is a narrative art.”  One of the most painful but beneficial parts of participating in an accelerator (Moneythink was in FFWD’s inaugural class) was rehearsing my pitch.  A few things I’ve learned:

-Slap stats are a good way to grab attention

-Use an unexpected turn of phrase to evoke a smile (our CEO Ted is good at this; he often uses phrases like “put those benjamins in the bank,” which softens the audience and conveys our youthfulness)

-Connect the project to your own passions/motivations (I still struggle with this as I’m not one of the co-founders and our founder’s story is particularly illustrative — of our lean approach, of our youthful energy, of our big-hearted compassion, of our rootedness in the urban landscape — but time and time again, folks remember the passion and commitment of an organizational leader that has communicated his/her personal connection to the mission)

-Don’t shy away from sharing your BHAGs (big, hairy, audacious goals): I initially felt a little sheepish sharing the huge goals we had for ourselves; as a relatively risk-averse individual, I would have preferred to share our realistic targets for the next two years.  Push yourself to talk big during a pitch; paint the vision.)

-End with an ask.  A pitch is about asking for something (usually money), so be up front and ask for what you need at the end.  The pitchee (er, catcher?) is expecting it.

-But most importantly: tell a story.  This is the oldest adage in the book, but people will really hang onto your words when you get the connected to a user experience, to the story of why the app was created, the story of why you use the product.  Whatever it is, tell a story.

4.  Design is about moving from an existing state to a preferred one.  This is the most gorgeous definition of design I’ve ever heard, and I picked it up at the Cusp Conference earlier this year, an incredible design event that invited me to speak about design thinking in a non-profit setting.   I occasionally feel that there is no end to “design” — what’s the difference between strategy and design, for example, in a business setting?  (I’ve heard IDEO talk about “organizational design” and “business design,” for example.)  At any rate, this is about as good a definition as I’ve ever heard.  It’s nestled right up there with a definition for “poetry” that I picked up in an undergrad “Intro to English Lit: Beowulf through Shakespeare” lecture class I took as a freshman at the University of Virginia.  I had dreaded the class at first — it was a huge “gut” class with hundreds of kids in the lecture hall, and we’d then break out for discussion sessions with TAs once a week.  But the lectures — my God, the lectures!  They were absolutely phenomenal.  I could barely see my professor from the back of my 500-person auditorium, but I will never forget her defining poetry: “poetry is a distillation of emotion into a preconfigured form.”

5.  “A startup is a human institution developing something under conditions of great uncertainty.”  This is an Eric Ries classic — another great definition to keep in the ether.

Good Managers Are Made, Not Born — And Other Discoveries.

I went on my first run in over 2.5 months this past week while visiting family in Naples, FL for the Christmas holiday.  Earlier this fall, I struggled with an unfortunate health situation that prevented me from exercising.  It was simultaneous torture and joy to be told, frankly and dispassionately by my doctor, that I could not run for the next three months.  I actually despise running (“How can I have only run .63 miles?  It feels like I’ve been out here for hours!”) but know that exercise is good for body and mind and have the Catholic discipline to force myself to do it.  My father one time told me: “You can cure almost anything with water and exercise.”  I’ve clung to that potentially spurious adage for years, likely to my own detriment at times.  (I’ve prolonged many a cold by running in frosty climes prior to recovery.)

At any rate, on the four-mile loop around my parents’ neighborhood, I found myself stopping multiple times to jot down things I’ve learned at work on my iPhone notepad to bring to bear here in this toolshed over the coming year.  Some of them are bits of wisdom I’ve inherited from folks much wiser than I; others are half-formed observations and intuitions from my own direct efforts — flotsam and jetsam circulating and surfacing, some of dubious use and others, likely, a meaningful component of the lifelong professional credo I suppose I’m seeking to build through this blog.

At any rate, my taking stock from this past week:

1.  Good managers are made, not born.*  At my previous place of employment, the sharpest tools in the shed were promoted quickly to managerial roles.  I recall an HR consultant that was working with us on a range of unfortunate (and, in retrospect, petty and frustratingly time-consuming) personnel issues saying to me: “You know, too often, people that are good at what they do are promoted to a management role.  But what few realize is that management is a skill, and many of these people need support and training to be effective supervisors.”  I internalized this for some time.  On the one hand, I felt foolish for not recognizing this myself.  On the other, it made me feel relieved — I made so many mistakes as a green manager that I almost want to send thank yous and apologies now, five years later — and this wisdom made me realize that no one can be expected to knock it out of the park as a manager right out of the gate.

*Except for maybe my husband.  My husband may defy this truth.  He is a seriously talented people manager, and has always been.  It exhausts him, but he is wicked good at it.  He has incredible intuition when it comes to addressing people and situation in the workplace.

2.  A managerial promotion should not necessarily be a reward for good performance.  Related to the above, I read this fascinating post that makes the case that, especially in technical environments, management should not necessarily be the reward for strong performance.  I asked a friend of mine who works at Yammer about this, as I knew he’d been promoted from a senior programming position to management recently, and had encountered some challenges in the transition.  (We’d talked previously about the gaping differences between maker’s time and manager’s time.)  He had some interesting corroborative thoughts:

“About 3-4 years after college, I had the opportunity to manage people probably due to similar circumstances outlined in the blog post. At the time, I had no idea what I was doing and, now after looking back, know I definitely did certain things very poorly. At Yammer, I passed up my first opportunity to manage because of my first experience with management. I had a second opportunity at Yammer and decided to jump into it because I made a decision that I didn’t want to code my entire career. I went in knowing that I would have to learn how to be a good manager, so I had a different perspective than my first foray into the role. Going back to the blog, there are definitely senior coders that never want to manage. I have a few on my team. I tend to “reward” them through similar means (give them the projects that have a lot of impact), but I also force them to grow by challenging them to not be “owners” of the code. There are definitely some truths in that blog post, but everyone is a snowflake and sometimes people need to learn by getting burned (like me).”

3.  We may need to think outside the box to imagine an org structure not oriented around the idea that management is the only path for career progression.  When I first heard Matt Mullenweg, CEO of WordPress, talking in an interview at last year’s Lean Startup Conference about his truly distributed, remote, and flat organization, I probably shared the same amount of confusion and bemusement that his interviewee, Sarah Milstein, displays.  At times, Mullenweg comes off as a disconnected and spacey hippie, but there is some beautiful synchrony and integrity between his open-source product and his organizational ethos.  At WordPress, everyone works in small and fluid teams, and team leaders occasionally emerge and then step back.  There is no rigidity or structure to this, and becoming a lead does not mean higher compensation or my authority.  It’s difficult for me to imagine this sort of organization working well in any industry outside of technology, and even within technology, it makes me wonder about productivity.  But still, there’s something intriguing about his anti-hierarchical tack that resonates with the above observations.

4.  If someone else can do it 70% as well as you can, you should delegate.  I have to admit that my main struggle as a manager is relinquishing control.  I am a perfectionist and I will embarrassingly admit that I occasionally hold the unhealthy, rude, and overly egotistic view that I can do certain things better than the people reporting to me.  That’s why this bit of wisdom I picked up from a blog I read a few months ago was incredibly useful in terms of making the judgement call as to whether to delegate or own it yourself.

5.  A start-up is a human institution developing something under conditions of great uncertainty.  This comes from the maestro, Eric Ries, and I think this will prove to be a useful definition to have on hand.

Taking Stock: 12.19.2014

I recently attended The Lean Startup Conference in San Francisco.  I learned a lot that I have brought back to my work in Chicago, the most powerful of which is the liberating discovery that everyone fails in the product space, and that your strength as a product lead stems from resiliency and faith in the process of iterative design.  (As an aside, it makes me wonder if we shouldn’t call product people “process people.”)  I took away a lot of gems, some useful activities and frameworks, and a newfound appreciation for the art of the presentation.

My favorite quote of the entire event came from Dan Milstein, who said:

“Lead by owning the questions, not the plans.”

Despite a broadly positive experience, I did bristle at the cultish-ness of the event.  There was something distasteful about the “us” vs “them” rhetoric woven throughout the presentations, as though all conference attendees were of the enlightened ilk while the rest of “upper management” and “the establishment” were blindly and mindlessly using antiquated, problematic, and unsuccessful techniques.  I do happen to believe that the lean startup methodology should be the ethos of the modern tech company, but there is also the question of what happens when a company grows up and necessarily needs to focus on efficiency vs. innovation in order to scale cheaply.  Perhaps it’s unfair to position these two forces at opposite ends of the seesaw, but there was something in the language of many-a talk that made we want to push back a bit, made me want to understand whether there are certain environments, timeframes, situations, etc., where lean needs to take a backseat to other forces for growth.

But this is probably the contrarian voice in me that draws back at any “us vs. them” formulation.

At any rate, one of the most helpful practices I picked up and will apply to my own work moving forward is what I will rename as the weekly learning inventory: a five minute activity each Friday to pause and take stock of major/top-of-mind learnings from the previous week.  I will be sharing these here each week.  A good hook to draw me back into writing more liberally about my observations and experiences.

Today I will share two weeks’ worth of inventory:

December 12, 2014

  • Lead by owning the questions, not the plans.
  • When it comes to pricing, ask for as much as you can with a straight face.  (Great advice from a mentor of mine out in SF.  I’ve been selling our technology to willing, like-minded partners and, despite a fair amount of research and consultation and thinking and reading, still feel insecure about the pricing model we have in place.  The process of validating it through customer conversations is not only time-consuming but also, from a personal standpoint, challenging for me.  I’ve never been in a position to ask for money.  My mentor had the above advice to offer, alongside the general provocation: “Ask for twice as much as you feel comfortable asking for.”  A speaker at LEAN corroborated this advice when he said: “If you’re not uncomfortable asking for money, you’re asking too late.”)
  • Our app is the space between nothing and a financial product. (Our COO Joe pointed out that our technology is sort of a stepping stone towards having a student open a financial product; I hadn’t been thinking of the technology as a trainer of sorts, but he’s onto something with this framing.)
  • Piloting something is a series of unpleasant encounters with reality. (#truedat)
  • Our app is best-suited to drive results around saving and mindful spending.  (We have been pushing to conceive of the app as a one-stop shop for issuing challenges across a range of financial habits and practices, but the photo-centric nature of the technology really fits in best for saving and spending habits.  It’s frankly challenging to envision interesting, generative challenges around safe financial product use or making money, though I’m open to pushback.

December 19, 2014

  • High achievers own the process, not the end product.
  • Most (even highly traditional) schools and folks that work in them view financial education as “dry.”  (An interesting re-framing of our value proposition.  I think that if we can sell them on the idea that we’re doing something fun, light, different to have huge, real impact, we’ll see lots of hand waving.)
  • At the end of the day, we are all humans with complex psychologies.  Business is not as rational as one might expect.  (I have been slowly coming to this perspective over the past six years.  Everything we do is driven by humans, their motivations, their passions, and their hatreds.  This is so basic that it’s almost embarrassing to write, but I have been recently struck by the power of truly thinking through the motivations of the person across the table, whether it’s a partner, a mentor, a student, a staff member.)
  • “I wish access was enough.  I wish education as enough.  But they’re not.”   (An interesting speaker from Ounce of Prevention mentioned this during an event I spoke at earlier this week.  She was provoking some of the students that had completed a class on human centered design and put together project pitches to think beyond education, beyond access — what will really drive change in a community?  This gets to the point above.)
  • Lean methodologies are a continuation of the human centered design process.  (I see them as tightly related, and possibly not in a temporal sense.  There are a lot of different overlaps.  I think that HCD is centered upon a language of empathy whereas lean is more about analytics and growth, which shade them in different ways, respectively.)

How Do You Know It’s “The One”?

I have a post-it on the front of my Moleskine notebook that accompanies me everywhere: “What is the ONE metric that matters?”  I keep this visual to remind myself to constantly keep high-level programmatic goals top-of-mind as I navigate our decision-making as a start-up non-profit.  But how do you know what metric matters most in a field that has, to date, been using inadequate proxies for measuring financial literacy?  In our field, most of us measure impact by looking at student-reported data from surveys centered around knowledge gain and attitude change.  Can you define a mortgage?  Are you more likely to set a budget because of this program?  How much money will you earn if you put $500 into a savings account with .05% interest?  (By the way, some measure impact even more imprecisely by simply reporting the number of youth they have reached.)  But none of these accurately tell you whether your student will actually be a more financially responsible adult.

Part of this is because it’s very difficult to identify a financially literate adult.  It’s far easier to point out financial illiteracy than it is the inverse: we know when we see someone spending beyond their means or paying off the minimum on their credit card for years or splurging on a want despite more pressing immediate needs.  But identifying a financially literate adult is far more difficult because it’s often what they’re NOT doing — how do you measure NOT spending?   In short, you can’t know whether someone is making good financial decisions based on a bank account statement.  It may be safe to say that most financially stable adults save regularly, spend less than they make, have positive net worth, and pay off their credit card bills on time — but for many of the students we serve — students living below the poverty line — these metrics may not be possible, despite their best efforts.  The other part is that no one knows what kinds of interventions will put teens on the path to good financial practices in the future.  Is it opening a savings account for a child?  Is it pushing kids to go to college?  Is it teaching kids how to budget?  These are moving targets that we think about — and extensively — on a daily basis.  I have had more conversations than I can count exploring the intricacies of this thinking — and that’s just trying to figure out what the end goal should look like.  The waters get muddier when you think about the early indicators that help us know our kids are on track, and, beyond that, the one metric amongst many that really matters in making that determination.

We’re right in the muck right now, talking through and around a refined impact measurement framework that encompasses a lot of these questions and concerns, but we had a phenomenal conversation with one of our board members, Shayne Evans, Director of both the University of Chicago Charter School and Urban Education Institute, that proved helpful to me and that I in turn wish to share out.  He showed us the framework he uses at his charter high school.  The end goal for him is college graduation for all of his students.  He then backwards designs from that goal by identifying various metrics that help him determine whether his kids are on track while in high school.  He clusters these metrics into high-level categories — High School Success, Student Progress, School Values — and then provides primary and secondary measures for each that he can then report on regularly.  Despite the fact that he tracks a number of different metrics, he advised us to track many, but commit to one — and then really build it out and reflect growth.  You can always move on to another metric once you’ve significantly moved the needle, but focusing on, say, 15 different metrics results in confusion and imprecision.  You can also begin by using imperfect measures — proxies, almost — and continue to iterate until you have the right measure and the right data coming in.  But the end goal is to communicate continuous growth on one important metric and then be able to explain both the importance of that metric and the reasons for its growth in a convincing way.

Returning to my initial question: how do you know your metric is “the one”?  I think part of this is thinking carefully through desired end outcomes.  What do we want our kids to report back to us regarding their financial situations when they are adults?  And then how do we backwards track those goals to what we can realistically accomplish within the classroom?  If we want all of our kids to grow up and budget, what do we need kids doing when they are 17 years old and have no regular income?  What’s realistic?  I think we’re getting close to identifying some leading metrics, but part of it, as one of our other board members said, will be “a big leap of faith.”

Mount Helicon for Entrepreneurs?

In ancient Greek literature, poets in search of inspiration trekked to Mount Helicon, home to the muses of the arts.  This artistic ritual came to mind the other day when a business friend of mine shared that his organization had recently established an innovation department, and was spending a lot of time reading and thinking about inspiration: “Where does innovation come from?  What are the conditions that cultivate it?”

I had two separate and distinct thoughts.  One was that it might be impossible to identify these conditions.  Having recently read Daily Rituals, a book that presents the varied creative practices of different geniuses, artists, writers, and thinkers in short 1-2 page snippets, it was easy enough for me to say that it takes all kinds of kinds to create, and that all those different kinds have wildly different practices.  There’s no one artistic temperament: some live ascetic, monk-like existences, others indulge freely in drink and drug; some need social engagement, others recede from it; some are methodical about their artwork, “working” on regular schedules, while others might go months without producing anything and then create a lot all at once.  Now, I realize that artistic production and innovation are not necessarily synonymous with one another, and that we shouldn’t let that unexplained metaphor pass us by.  But at the same time, both revolve vigorously around principles of good design and are fueled by creativity and an ability to see the world around us (or some bit of the world around us) in a new and different light.  So, let’s accept, for now, that possibly flimsy logic, and push beyond.  Returning to the book: I instantly thought that perhaps innovation springs from a range of different contexts.  I thought about IDEO’s human centered design process, which truly begins from the ground up.  And then I thought about more the “lean startup” model, which posits that you can hedge your bets on a good idea — so long as you quickly and regularly test it and change tacks accordingly.  In these two models, innovation comes from two rather different processes.  At the same time, I would say that the only unifying tie that bound the miscellany of stories in the Daily Ritual book was that almost all of the creators afforded themselves some amount of “maker’s time” — that is, swathes of time dedicated only to creation, uncluttered by the noise of daily life.

So this led me to my second thought: perhaps there are certain general conditions that enable us to create and innovate and iterate more readily.  I began to think more critically about the times where things have really begun to “gel” or “click” or whatever the right motion is there — where new ideas come to a head, presenting themselves with a dramatic curtsy in that awesome moment where you realize: “YES, that’s what it is!  That just feels right!”  A couple of different useful contexts came to mind:

(1)  Structured time to talk through an idea or a cluster of ideas or a “cloud” of ideas — i.e., some nebulous mix of concerns and concepts that you just know you need to think about — with your smartest, most open-minded colleagues.  Sometimes you just need to sit down with your brain trust to talk through an idea from top to bottom, throwing everything out there.  (Everything.  Let it all hang out.  I recently floated the idea of trying to seek a federal charter for a national youth credit union so that we could create the ideal financial product for our teens, as there’s just nothing out there on the market that is meeting our expectations.  And we are a three-person organization with a fairly massive mentorship machine in place.  So — think big, too.)  You’ll be surprised at what comes out of the jostle and shake of ideas — people emphasizing new aspects of the problem or introducing new ones or going off the deep-end.  I’ve come through a lot of challenging points by talking things through with my wicked smart colleagues when I’ve suggested we block off an hour or two and really slog through something.

(2)  Implicit in the above, but: complete open-mindedness.  If you feel yourself constructing a wall that you won’t let yourself beyond (i.e., “no, we couldn’t offer our kids prepaid cards because schools will resist the idea of product placement and will probably be more comfortable with savings products anyway, which are almost indisputably well-received”), push beyond it and continue to explore.  Having colleagues that share that unbridled will to explore is an incredible gift, so you should seek them out in your organization or encourage this and lead by example.  (At my previous job, we occasionally encouraged one another to use the phrase: “Yes, and…”  — a technique from improvisational comedy that encourages comedians to build off what their cast-mates have just said to keep the story going rather than nipping things in the bud prematurely.)

(3)  To balance the structured brainstorm sessions — big greenswards of “maker’s time.”  Time to just tinker, think, read, reflect.  This was really hard for me to adjust to after living on manager’s time for so long; I felt like I was being unproductive.  But I really needed it in order to fulfill the duties of my role as Chief Innovation Officer.  And I continue to need to remind myself to set this time aside and leave it unencroached by the noise of email, checklists, and the like.  Sometimes I need to do other “things” to occupy myself physically during this time — exercise, or read articles, or jot down notes, or write open-ended Word documents to myself, or, dans la facon d’IDEO (in the IDEO way), write down a lot of post-it notes to capture a lot of different, distinct thoughts — but those mornings where I’ve cleared my schedule until noon or even later to really think through a specific problem or issue are inevitably the most fruitful part of my week.

(4)  Talk to a lot of people.  Like, a ton.  Our CEO, Ted, is an absolute networking beast.  He’s connected me with what feels like half of the city of Chicago and I’ve had the most incredible range of conversations as a result.  To be frank, maybe 10% or less of these conversations actually leave me thinking: “Oh, interesting, that helped me solve this problem.”  But they help me situate my thinking in really interesting ways.  For example, learning how for-profits orient themselves prior to an app launch helped me think through the launch of our app as a non-profit in a new and different way.  And learning about the metrics that gaming apps conventionally use to measure their engagement helped me think more critically about our app because I realized many of them did not apply or did not matter to our model.  Talking to a lot of people also helps you nail your pitch — great practice for delivering it to the big guns down the road.

(5)  Related to the above: read a lot.  And from a wide and varied range of sources.  You want to read the obscure blog post from a teacher in Missouri bemoaning the technology issues in her classroom, and the platitudes (or rants) from the CTO of a school district, and the blog written by the product manager of a new ed tech company, and the Washington Post’s op-ed on MOOCs, and the Tech Crunch article on a new Google acquisition, and everything in between.  Read, read, read.  And use Pocket to help with this — I tag all of the articles I read so I can quickly search my tags and call up articles I read that I want to reference down the road.

With this blend of practices and conditions, I’m convinced you can really drive innovation in your own organization.  The issue, I think, is that many organizations are not outfitted to accommodate this due to various institutionalized processes and rituals.  I’m curious to know how, for example, Coke handles their innovation team — does it function differently than most of the other units?  How so?