The Greatest Startup Story of All-Time

Tim Westergren and his rugged journey founding Pandora is the greatest startup story — by far — that I’ve ever heard (or maybe second to the Founding Fathers  starting America).

I was meeting with a friend last night to discuss her startup.  We were talking about the mindset of absolute persistence it takes to be successful.  This morning, I sent her the NYTimes article, “How Pandora Slipped Past the Junkyard.”  I think it’s so inspiring that I keep an excerpt tacked to my desk:

By the end of 2001, he had 50 employees and no money. Every two weeks, he held all-hands meetings to beg people to work, unpaid, for another two weeks. That went on for two years.

Meanwhile, he appealed to venture capitalists, charged up 11 credit cards and considered a company trip to Reno to gamble for more money. The dot-com bubble had burst, and shell-shocked investors were not interested in a company that relied on people, who required salaries and health insurance, instead of computers.

In March 2004, he made his 348th pitch seeking backers. Larry Marcus, a venture capitalist at Walden Venture Capital and a musician, decided to lead a $9 million investment.

“The pitch that he gave wasn’t that interesting,” Mr. Marcus said. “But what was incredibly interesting was Tim himself. We could tell he was an entrepreneur who wasn’t going to fail.”


Let’s do a little math: from the beginning in 1999 to his breakthrough investment in 2004, Tim gave 348 pitches in roughly 225 weeks.  That’s three pitches every two weeks for five years — PLUS being told “no” about 99.9% of the time. 

Not only was Tim’s pace unbelievable, but he had to withstand the brutal mental hardship of repeated rejections all while shouldering the responsibility of payroll, revenues, and strategy.

Some might say this level of persistence is actually naive or bad business.  Sure, it turned out well, but to go on as long as he did without the traction he needed may not be the smartest thing.  I totally get that. But it doesn’t make this story any less awe-inspiring.

Thanks, Tim, for the example you set.


Who is Validating You?

If I created a list of the five most important things for a young, nonprofiit startup founder, this would be tied for #1:

Third-party validators.

And let me put an even finer point on it: Third-party validators with access to philanthropists.

This was the make or break for my organization in the earliest days.  We were extremely fortunate to have the confidence of one of the best social entrepreneurs around, Alan Khazei — co-founder and former CEO of City Year and Be The Change.  He was so fired up about what we were doing that he was willing to make introductions to potential funders.

Very importantly, he also did more than just make intros — he consistently helped us in a ton of ways.  To potential funders, this says: someone I trust is keeping an eye on things and that’s important because I don’t have time.

And it paid off.  Just a few months into the startup period, Alan helped us secure two meetings with two incredible leaders and philanthropists.  We didn’t have a big strategic plan or every question answered.  We had a clear need and a clear way to pilot our solution.  A few weeks later we had $5k and then a little bit after that we had a 1:1 challenge grant for $50,000.

After the second meeting, Josh (who gave the challenge grant) told Alan specifically that he didn’t have time to work with us on a regular basis and asked Alan if he did.  Alan said yes, joined our board, stayed involved (still is), and Josh issued the challenge grant.  We matched it 82 days later.

In a video interview, Josh describes similar situations.  He says:

A social entrepreneur is doing a startup, and unless you have the time to do due diligence yourself or unless you have someone else who’s going to be involved to watch over it for you, don’t donate.

You can watch the entire video and others on a great site, (scroll down to the video titled: “No foundation, no staff: Josh Bekenstein leverages knowledge from trusted philanthropists and experts”)

That leaves the question — who is the third-party validator who can open philanthropic doors?  It’s hard.  For my organization, we’re trying to build a grassroots movement to make national service programs like AmeriCorps a political priority.  So Alan, as a key stakeholder of AmeriCorps, made a lot of sense.  And many others have followed his lead in helping us.  And that has been invaluable.

Trusted relationships are the most important currency.  And Alan (and many, many others) gave us a lot of their “relationship capital.”

Unsolicited advice for young nonprofit founders: find the people who care about your success, have access to philanthropists, and earn their trust…quickly.

Articles of the Week: Making Yourself a CEO, 5 Changes to Nonprofits in 2013, How to Allocate Your Time, and more

Making Yourself a CEO by Ben Horowitz

The article is largely about giving feedback and really well done:

To become elite at giving feedback, you must elevate yourself beyond a basic technique like the shit sandwich.  You must develop a style that matches your own personality and values. Here are the keys to being effective…

5 Things that Will Change the Way Nonprofits Work in 2013 by Suzanne Perry, Caroline Preston, and Cody Switzer in the Chronicle of Philanthropy

How Mike Rothberg Went from Sleeping on Couches to Running a $5 Million VC Fund by Alyson Shontell

You might read this and say “Yeah, he went to Stanford and Harvard, giving him a great network.  He’s basically starting from third base.”  Certainly helps a ton.  But what I love about this story is the bare-bones living and do-whatever-it-takes approach.

How to Allocate Your Time, and Your Effort by Elizabeth Grace Saunders in

One of the better time management articles I’ve read — a ton of great actionable advice.

The rules changed when I started my own business over seven years ago. I realized that doing A-work in everything limited my success.

Q & A with a Startup Founder: Emily Cherniack

This post is part of an ongoing Q & A series with startup founders, experienced social entrepreneurs, fundraisers, and philanthropists to help aspiring or current startup leaders make big things happen.  The first installment is with the amazing Emily Cherniack, founder of New Politics.

Describe your organization in 3-5 sentences:

New Politics is a political organization that embodies a “human capital” strategy to improve the outcomes of our politics and governance– anchored by alumni of the service and social entrepreneur movements. Our vision is that one day our political system functions more effectively because a majority of our political leaders have first dedicated themselves to a period of national service and thus are undaunted by our toughest challenges, work to find common ground, put our communities first, and solve our problems.

New Politics works to achieve this vision by recruiting, training, providing support, and electing candidates to local and state offices and building a grassroots base to do so.

Where are you in the startup phase (how long, are you full-time, etc)?

New Politics is almost 6 months old.  The organization started out as an idea with some initial conversations in March and by end of July I was working full time on the organization.

How did you get into the position of leading a new venture?  And what motivated you to “go for it”

I actually never thought that I would start an organization.  I am much more of a behind the scenes person and spent the past few years in the role as Chief of Staff to the amazing social entrepreneur Alan Khazei.  I had just finished leading his U.S Senate race and was looking for my next job opportunity.  Ever since I worked on my first campaign in 2009 I had been fascinated by the entire candidate process and wondered why more people from the service and social entrepreneur space weren’t running.  To me, these were the amazing leaders who should be running for office.  I was also seeing the challenges our elected leaders had in their lack of ability to work together.  It was at this point I realized that this was something that was desperately needed.

How do you handle mistakes and setbacks?

When starting an organization, it’s important to keep in mind that you will make mistakes and you will have setbacks.  Nothing is going to be perfect, or work out exactly how you think it will.  I have found that mistakes and setbacks are an important learning tool for reflection and figuring out how to improve.  My first big mistake happened when I went to pitch my first potential donor.  I totally thought he would support this new idea, which would help give me some resources to work on this full time.  As it turned out, the person did not like this idea and was definitely not going to support it.  I was at a loss because I was so sure I would get his support that I had no other potential donors lined up to meet with and had no idea what to do about getting start up funding.

After reflecting on this setback I realized that I made a mistake going to this person so early in the development stage.  The idea wasn’t really complete yet and I should have waited before approaching him first.  I also realized not to put all your eggs in one basket.  It’s important to meet with as many people as possible because you never know who will be inspired and who will want to support you.  My first key supporters were people that I actually did not think would be the first ones in and now I have some great champions who have the energy and belief in this idea to be long term advisers and mentors.

What are the most important skills and characteristics to start an organization?

No one is going to have all the skills they need to start an organization.  The most important skill is self-awareness and knowing what you are good at and what you need other people for.  I think being a great relationship manager is very important because you have to connect with people whether it is donors, potential team members/staff, your board or advisory committee.   Communication is also a skill that is incredibly important for a start up.  You have to be able to communicate your vision and what you are trying to do.  It’s something that I have been working on because it is actually not my strength.  The more you can communicate simply what you are doing, the more people will want to be involved in it.

Commitment is also important.  There is a saying at City Year, where I used to work that “your commitment brings about the commitment of others”.   I truly believe that the more passionate and committed you are to your organization, the more others will feel that energy and want to also be involved.

How did you decide to “go for it” and start your organization?

I had finished a political campaign and was looking for another job.  I had been thinking about this idea for awhile but never had the opportunity to do anything about it and realized that this was the time—now or never.   I truly believe that if we don’t get the best people into politics that our country will not get back on track and I didn’t want to sit on the sidelines anymore and wait for that to happen.  I also think life is short and I figured that if I didn’t start this now, I would always look back and wonder, what if?  I would rather take risks, start something and fail then be afraid to fail.  My motto is “Go big or go home”.

What’s the hardest part about starting an organization that you didn’t expect?

I didn’t expect it to be so lonely.  I am hoping to have more resources soon to build a team but even with that, it can definitely be lonely being a leader.  At the end of the day, you are the one that has to keep plugging along and setting the vision for the organization, and that can sometimes be very lonely.

What types of advisers should a founder recruit?

It’s important to recruit people who can balance your strengths.  For example, if you are not a great fundraiser, you should recruit someone who has that experience to be helpful to you.  It’s important to have a balance of skills and diversity from your advisers.  If you are working in diverse communities and all your advisers are white men, you are not going to have diversity in perspective.  It is also important to have advisers you can be totally honest with.  Save the dog and pony show for other situations.  Your advisers should be people you can trust to say the tough things to, admit mistakes, and truly ask for help.

What characteristic of your personality to use the most as a startup founder?

Starting an organization is really hard and the one characteristic I rely on the most is perseverance. I have found that having the perseverance to accomplish a long-term goal no matter what obstacles or challenges are has been key.   There have been several times that quitting would have been easiest but it’s been my willingness to stick with it, even when others thought I should give up, has been the most important characteristic I have used in this endeavor.

Articles of the Week: 5 Tips to Become a Master Networker, Creating Company Culture, and More

A round-up of my favorite articles from the week that could be helpful to aspiring entrepreneurs, startup founders, and anyone looking to make something happen.

Become a Master Networker: 5 Quick Tips

Best explanation of what makes the best networkers I’ve seen.  Some of it might feel counterintuitive or counterproductive, but it’s spot-on.

Programming Your Culture by Ben Horowitz

Ideally, a cultural design point will be trivial to implement, but will have far reaching behavioral consequences. Key to this kind of mechanism is shock value.

The Future of You by Thomas Chamorrow-Premuzic on

Welcome to a new era of work, where your future depends on being a signal in the noisy universe of human capital. In order to achieve this, you will need to master three things: self-branding, entrepreneurship, and hyperconnectivity.

Managing Startups: Best Posts of 2012 

Articles of the Week: 10 Reasons People Resist Change, 5 Mentors Every Entrepreneur Must Have, 1 Simple Trick to Creativity, and More

A round-up of my favorite articles from the week that could be helpful to aspiring entrepreneurs, startup founders, and anyone looking to make something happen.

10 Reasons People Resist Change by Rosabeth Moss Kanter, Harvard Business Review

5 Mentors Every Entrepreneur Must Have by Joanna Lord,

5 Ways to Push Your Company Past the Startup Phase by James Green, Mashable

1 Simple Trick to Creativity — Constrain Yourself by Daniel Epstein,

How Nonprofits Convince Millennials to Give: Customize the Cause by Victor Luckerson, TIME

Gift Ideas for the New Social Entrepreneur in Your Life

A couple of weeks ago I suggested five holiday gift ideas for a startup founder.  Here are a few more:

Management Training Courses

The Management Center does outstanding work. I’ve attended a training and put the lessons to work.  Good for managers at different levels and well priced.  Details and dates here.

If you’re looking for a cheaper option in this area, the book by the leaders of The Management Center, Jerry Hauser and Alison Green, is a must-read.  I had my team read it and I refer to it regularly.  Managing to Change the World: The Nonprofit Manager’s Guide to Getting Results.

And if you’re looking for an even cheaper option, you can sign-up your special someone for their free newsletter.

Harvard Business Review Subscription

90% (maybe more) of the articles are not about social change explicitly.  But as French novelist Marcel Proust said, “The real act of discovery consists not in finding new lands but in seeing with new eyes.”  That’s what the research, discussion of innovation, and lessons from other fields will do for a social entrepreneur and founder.

It’s one of the more expensive subscriptions, but you get both monthly magazine and complete online access.

Fast Company and Inc. Magazines

Want to give a thought-provoking magazine but less expensive than HBR.  These are two good options.

Social Innovation Articles of the Week: Restoring the Soul of Politics, Forbes 30 under 30, Ugly Sweaters, and What’s Your Story

How Technology Has Restored the Soul of Politics by Joe Trippi

The setting is politics, but the lessons are larger — the diminished role of “experts” and the erosion of top-down messaging.  Good lessons for a young entrepreneur in any field.  The money excerpt:

But the outstanding fact of the 2012 election is that the pollsters, consultants, advisors, and political gatekeepers who guarded the old way of doing politics lost bigger than Mitt ­Romney or the Republican Party itself. There is perhaps no human activity where power is so jealously protected as it is in professional politics. The old guard will try to demonstrate its usefulness for a few more elections, and some will doubtless adapt. But its dominance has passed.

30 under 30

Forbes is out with its list of 30 under 30, including the categories of Social Entrepreneurs, Education, Energy, Law/Policy, Science/Healthcare, and more.

Ugly Sweaters

Great idea to use the fun of ugly sweaters to raise money.  Routine activities are important (that’s why they become routines).  But that also means they become less noteworthy and that’s a challenge when it comes to things like end of year fundraising.  I’m always a big believer of applying the creative to the routine.  That’s how to break through the noise and get attention.

Some wear ugly sweaters.  Others don’t wear shoesSome grow mustaches.  One company is selling a mundane product with a hilarious video (7.7 million views!).  And a new advocacy campaign convinced its elder leader (and former Senator) to dance Gangnam Style (coverage in CNN, USA Today, NPR, and 170k video views).

What’s Your Story? The Answer May Land You a Job

Pitching a potential investor or coalition member is very similar to a job interview.  They are sizing you up as much, if not more, than the organization or the cause.  After all, as a leader/founder you and the organization are pretty much the same thing.

That’s why I found this interview with with, Karl Heiselman, CEO of a big brand consulting firm, so interesting.  To the question: How do you hire? What qualities are you look for? He answered:

The first thing I always ask is, “What’s your story?” The way somebody answers that is a pretty good indication of what they’re all about. If they’re just talking about the job, I find that really unattractive. If I feel like they’re being sincere and honest about what it is that they want to do with their life, even if it doesn’t line up exactly with what we want in our position, I find that far more attractive. When you ask people, “What’s your story?” they can answer that a million ways, and where somebody goes with the answer is a pretty good indication of who they are.

In a meeting with potential donors, of course outlining the need, progress, model, and strategic plan all matter a great deal.  But as Alan Khazei taught me, “People give to people.”  Your story of self matters a lot. It’s not a distraction or self-centered to tell it.  It can be the difference between a new donor, advocate, coalition member, or ally — or not.

For inspiration, do yourself a favor and watch Jim Gilliam’s “The Internet is my Religion” — so moving.

Articles of the Week: How Well Do You Take a Punch, Best Productivity Apps of ’12, Emotion v. Knowledge, and Icarus Sessions

How Well Do You Take A Punch? by Fred Wilson (investor in Twitter, Tumblr, Foursquare, etc.)

Best Productivity Apps 2012 from Business Insider

Startup founders and teams have a lot going on.  Check out some tools to make it easier.  I was surprised to see Asana left off the list. Started by a Facebook co-founder and getting lots of praise.  It’s what I use.

Why Emotion, Not Knowledge, Is the Catalyst for Change by Dan and Chip Heath for Fast Company (authors of two of my favorite books, Switch and Made to Stick — amazing books for anyone who is trying to make anything happen.)

The Icarus Sessions — go present your idea to others in 140 seconds.  Sessions happening around the country.

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