One month, 100 rejections

There are great reasons, as a nonprofit, to look for long-term, sustainable sources of revenues, to build a business model that brings in earned income or investor capital.  Philanthropic funds are so hard to come by and often so expensive to raise.

But I also see a lot of intellectually appealing arguments made by founders about not being a traditional nonprofit, when what’s really going on is that they’re just not willing to get out and fundraise.  I’ve seen missions contorted and organizations drifting far away from their original purpose because a founder has decided “I’m not a fundraiser.”

The best part is: all of the best fundraisers I know also say “I’m not a fundraiser.”

(except for one, Jennifer McCrea, who is putting the mojo back into fundraising.)

Here’s the thing.  Most people aren’t fundraisers.  Most people find it petrifying at first.  Most people fail at first, feel like they are hitting up their friends, even feel a little bit ashamed.

But the part I really, truly don’t get is how you could be willing to devote years of your life to a project but not be willing to ask people to fund it.  And I don’t mean write grant proposals, I mean ask people who are philanthropically active to write a check to help make your dream possible.

So here’s my pitch: this thing that you’re willing to devote your life to?   Take one month and get out of the building, knock on every door you can, and promise yourself that you won’t stop until you’re actually rejected 100 times.  Keep track of the 100 rejections so it’s real and you’re making progress.

Because I’m positive you can survive 100 rejections.

Because I’m positive that even if you get rejected 100 times, your idea will get stronger by virtue of talking to all of those smart people.

And because I’m sure that if you set out to get rejected 100 times you’ll raise the money you need long before you hit 100.

More not less

Recently I had the chance to attend a roundtable discussion on how to scale innovations in global development.

One of the participants, a successful serial entrepreneur, related an important and telling story about why it’s hard to seed innovation in the nonprofit sector. She said she’d raised $200 million in her life, $190M in her four for-profit enterprises and $10M on behalf of nonprofits that had important innovations that needed funding.

With her for-profit ventures, her experience was that when she’d ask a venture capitalist for $1M to fund a new innovation, if they said yes to funding they would typically invest $1.5M or $2M because they knew that she probably needed more money (“runway”) to get it right – that there would be twists and turns in the road, and that the best way to minimize her chance of success was to underfund her.

Her nonprofit fundraising might have the same starting point: asking for $1M to fund a new innovation. In one case she was working on raising $1M from a foundation, and they approved the funding. However, though she asked for $1M they had only approved $750,000 of funding. I wish I’d found this outcome more surprising. If anything I was expecting her to say they gave her $100,000. But the story about VC fundraising was news to me, the idea that a funder would often tell the entrepreneur that they’d asked for too little money.

A big part of what holds us back in the nonprofit sector is that we’re stuck in a program delivery mindset. In that mindset your philanthropy is paying for a set of defined tasks and as a donor your goal is efficiency. And if efficiency is your goal, you might be right in thinking that you could eek out more bang for your buck by giving a little less money than you were asked for.

But new ideas are different – you’re not aiming for efficiency you’re aiming for success. That means that giving less than what’s needed or doing things like challenge grants or other mechanisms designed to “catalyze” other funding are probably a terrible idea. An underfunded innovation cannot get more efficient, it can just have too little cash, which will either suffocate it or force the entrepreneur to spend more time fundraising and less time building the business.

Once we decide a new idea is worth funding, might we take a page from folks whose job is to bet on innovations and write bigger, not smaller, checks?



When I grow up

It wasn’t until three or four years ago that I figured out what I wanted to be when I grow up. Not what specific job, not each twist and turn of my career. The characteristics of a job that is right for me: my strengths, where I shine, where and how I can deliver value to an organization.

While I’d feigned clarity and direction in countless prior job interviews and graduate school applications, I felt like I didn’t know in any real way where I was headed. I knew I’d been good at school, and since graduating college I’d managed to figure out a lot of things I didn’t like. But I still had a pretty limited affirmative understanding of what I was put on this earth to do.

No doubt our educational institutions are a huge part of the problem. Even in graduate schools, which are meant to prepare students for the next stage in their careers and to help them get there, I spent 99% of my time “learning stuff” and 1% of my time trying to figure out who I was and what made me tick. That can’t possibly be the right balance, yet that’s how nearly all of these programs are structured. (Sure, part of this is on me. I made the mistake of thinking Business School was school when it didn’t need to be.)

I can’t overstate how many incredible people I meet who have no idea what they’re supposed to do with their lives.

So, first and foremost: it’s OK that you don’t know. It takes time.

Second, this notion of figuring out exactly what you want to be when you grow up is an anachronism. It’s time to dispense with the preschoolers’ notion of careers (doctor, lawyer, footballer, firefighter) which is pretty much the only mental model we all have. Instead, the work begins with exploring questions like: what am I best at? What things seem really easy for me that are difficult for others? When do I shine? What kinds of problems do I like solving? How much uncertainty makes me comfortable/uncomfortable? How much recognition do I need? From whom? Why? How much do I like risk? Am I more conceptual or concrete? Do I love ideas or execution? How am I at building relationships? Am I creative? Do I like to teach others?

I think we knew all this stuff once, and we forgot it.

A short story: weekends in my house are a juggling act bouncing between three kids. Yet last weekend I managed to get a few uninterrupted hours with my 8-year-old son, and I’d told him we could do anything he wanted. While all the kids in his class would likely use that time to play soccer or baseball (and yes if I’d let him we’d have played video games), his idea of a perfect afternoon was to go to a craft store, buy a box of popsicle sticks, a package of pipe-cleaners, a piece of green foam, a piece of Styrofoam, some Elmer’s gel glue, and, as a bonus, a packet of fake moss, and then spend a few house building a model playground from scratch in our basement. Voila:

I have no idea what my son is going to be when he grows up, and I don’t suspect that he’ll know that for a while. But I know that he gets joy out of creating things and out of using his imagination. It engages him fully. In some way and in some form, he’s going to have to make stuff if he’s going to be really happy.

That’s the only level at which I’ve been able to figure out what I’m meant to do in the world. It’s not a shingle I can hang on the door or a defined career in any traditional sense of the word. What it is is a first-time understanding of who I am, of what the organizations I’m part of seem to need from me, of roles I continually find myself playing whether I choose to or not.

Slowly, the outline started to form, and once I saw that initial outline, my job was to keep trying to get the picture into sharper focus. Still lots of work to do – a lifetime of work – but it feels a lot easier than groping around pretending that I’m supposed to fit myself and my career into some little box I first heard about when I was a little kid.

There are fewer and fewer boxes out there, and you probably don’t want to fit into any of them anyhow.


I was having a tough day.  Lots of work requiring real emotional energy.  I was feeling drained.

On my way home a guy is jamming on the jazz piano.  Just jamming.

I keep on walking.

Then I stop.

I turn around.

I drop $5 in the bucket.

We exchange a few words.  We both smile.  Both our days get better.

There’s joy in giving.  Real, actual joy.

Nothing intangible about it.

Goldilocks giving

When it finally comes time to ask someone to make a philanthropic donation, how much should you as for – a little, too much, or just right?

“Too little” is never right.  If anything, “too little” is a polite way for someone to say “no.”

“Just right” in my experience also isn’t the answer.

Why?  Because we need to ask the most of everyone if we are going to accomplish great things together.  To be our best we all stretch, we reach just a bit too far, we dream audacious dreams because before something can happen we have to imagine that it just might be possible.  So too with giving.  It should be a stretch, should feel a little outlandish and a bit impossible.  At that moment of connection and excitement and commitment, people will go a bit further if you ask them – and even if they don’t no one gets hurt along the way.  We’re all grown-ups here.

This is particularly important because of how people tend to approach renewals of their giving.  While occasionally someone who gives at a low amount relative their other charitable work will jump to a significantly higher level, those sorts of shifts are rare.  Which means that if things work out well, the giving conversation you are having about this year is setting the bar for giving for next year and the year after that and…

In this case, “too hot” is better than “just right.”

Bok choy, not chicken

One of the things that I’ve discovered about being a (mostly) vegetarian / (sorta) vegan* is that if I don’t plan accordingly I will nearly always be starving whenever I fly anywhere.  The vegetarian options on a plane are inevitably either very sad salads or cheese plates, hence the hunger.

Last week when getting off a plane in San Francisco I had an extra 10 minutes before being picked up at the airport, and I found a small place to get Chinese food, mostly stir-fry.  You’ve been to this place and its many cousins: pick the entrée (chicken, beef, etc.) to go with your noodles or rice for $10.  As usual there was no non-meat option, which to me means no lunch option, so I asked the woman behind the counter what I could do and she told me that they’d be happy to whip up a vegetable stir fry (for $16, but that’s another story).

This got me thinking about doing what I want versus following rules that I set for myself.

The omnivore I used to be would have happily and without a second thought ordered the chicken or beef entrée.  The vegetarian I aspire to be saw nothing to eat and asked a different question that led to a different outcome – one that I was just as happy with (and my omnivorous self would have liked just fine as well, but would never have dreamed of asking).  With the pre-existing rule in place I behaved differently and got a better outcome for me.

Reflecting on my ongoing exploration of the practice of generosity, it’s impossible to ignore that virtually every major religion has specific norms and expectations around generosity, giving, caring for others. When I think about what my generosity exploration is a reaction against, part of the answer is the modern, progressive, liberal, often not-so-religious worldview that is all too familiar to me as an American northeasterner who went to a liberal arts college.  In this worldview I’m supposed to be aware of and care about the world, supposed to believe in the role of government and believe in social safety nets, but in terms of how I individually am supposed to act, what’s considered right and wrong, sacred and profane, how I fit into a broader group (my community, my religion, my extended family) and how and when I subjugate what feels right to me to rules or expectations or group norms or tradition – it’s a conversation we rarely have and often don’t even know how to start.

What have we lost in this world free of constraints?  What do we give up when we shed rules, expectations, obligations, a sense of duty or service or respect for traditions?

The balancing act is that I am a huge believer in bucking tradition, in unshackling ourselves from a set of norms that keep us from contributing to our full potential, to recognizing all that we have to offer and all that the world needs from us.  At the same time I know from my own experience that creating a set of expectations – of rules – whether around food or a practice of generosity or, yes, religion causes me to take actions I wouldn’t otherwise take, actions that expose me to different experiences and different people and different behaviors….not each one exactly what I hope it will be, but more often than not I’m discovering wisdom and connection and a sense of place and belonging along the way.

How much do I really know what is best for me and how I carry myself in the world?  And how much are we all giving up when we give up our obligations?



* “(sorta) vegan” is what I’m able to pull off without embracing meat/cheese substitutes and/or avoiding nearly all foods and restaurants.  It essentially equates to low dairy.

24 hours

I keep wondering what people are getting at when they put a huge effort into shaking hands, making conversation and swapping business cards and then disappear off the face of the earth.

Almost as bad is following up days or weeks later to say how nice it was to meet.  By choosing to (re)start your conversation weeks down the line when you have the option to do it within 24 hours you’re communicating that lots of other things are more important to you.  This conversation is low on your list.

That may be right.  Just be clear that it is a decision.