Allyson Downey, Weespring, Entrepreneur

imgresSince I seem to have made into the women founders space Allyson was either introduced or reached out to me several years ago when she was in the early phases of Weespring.  It wasn’t for me but I got to sit on the sidelines and watch her grow even though she didn’t even know that I was watching.  She is on a listserv with me and she has become a vocal leader in the group.  I read that she had wrote a book , Here’s the Plan: Your Practical, Tactical Guide to Advancing Your Career During Pregnancy and Parenthood.  I have had this conversation with more than a handful of women.  It was time to tell Allyson’s story.

She grew up in Warwick, Rhode Island.  Her step-father was an entrepreneur.  He ran a series of side businesses from an electronics business to a record store in town to the concession stand at the local bingo hall and then a business that removed all the garbage from the local beach.  He made an impact on her growing up.  Her parents had divorced when she was 5 and he was a major part of her life.  Her Mom was a teacher in the local elementary focusing mostly on reading recovery and literacy.

Allyson’s first business was when she was 8.  She had gone to a festival and saw people painting faces and was blown away.  She started a face painting business for kids birthday parties.  She created a book, like the person at the festival, with pictures of all the different faces she could create.  She used her cousin as the guinea pig.  She advertised herself at the local health club with a sheet of paper and a phone number at the bottom that you could tear off to call her.  She said it is amazing thinking back on that experience that people actually hired her to paint 5-6 year olds faces at their bday parties.

She graduated high school and went to Colby where she majored in English.  She spent her junior year in Cork Ireland for one semester.  She had a good friend in Edinburgh that same semester so they traveled for a month afterward.  In the summers she worked even selling Cutco knives at one point.  She also taught creative writing classes at the Kemp school for junior high school kids and went on to run it one summer.

After graduating Colby she moved to NYC.  She had a boyfriend there who had graduated a year earlier and so she like so many other women I know followed him.  The economy was terrible and jobs were scarce.  Her thesis advisor suggested she go get her MFA and so she did.  She got into Columbia and although she wasn’t sure this is what she wanted to do the timing was right. She moved in with three other women who were in the publishing world and quickly realized her heart was not in it.  She was going to school and working for a literary agent part time because she was strapped for cash.  Full time in school, 25 hours a week for a literary agent and 10 hours a week tutoring too was insanely stressful.

Even though it was a tough road she landed her dream job as the editorial assistant for the cookbook editor at Doubleday.  She saw it as a way to be in publishing without having to interrupt her own writing.  Low and behold she never wrote a word of fiction but she did get to work on Jean George’s and Mark Bittman’s book.  She was 23 and life seemed kind of glamorous.

It was 2004 and she got bit by the political bug.  She did not understand why people her age were not voting and began organizing cocktail parties for her peers to hear people speak about politics and register to vote.  After 5 of them she got an offer to be a fundraiser for a campaign in upstate NY.  She called her parents to see if she could come home, get her high school car and live in upstate NY for 6 months.  They thought she was insane but supported her decision.

Allyson went to work for a 26 year old Democrat woman who was running for Congress in a Republican district.   Despite the fact that this woman loss significantly Allyson got noticed. She was offered 5 job opportunities for major campaigns.  She took a job with the Spitzer campaign and become number 3 in the fundraising group.  Over the next two years she worked her ass off trying to build up her own profile without stepping on anyone’s toes.  She was to raise money from the women’s movement for Spitzer which in hindsight is hilarious.  It isn’t easy getting $250 from a woman (it is consistent in start-up fundraising too) but Allyson targeted upstate where the other two fundraisers were in the city.  She raised $5m over a year and a half.

Not surprising she kept on taking on more and more responsibility.  When it was time for Spitzer’s NY convention she rented out the baseball field in Buffalo bringing on Jimmy Fallon as the emcee with a line-up of Natalie Merchant and James Taylor put together in a mere 8 weeks with a $1.5m budget.   What she loved about the political world is that there were zero constraints on your age, if you could get shit done you were given responsibility.  While Spitzer was just entering the office the conversations began around the post campaign and they asked Allyson to run his re-election campaign.  She took it on with the goal of raising $6-8m the first two years he was in office and $12-15 the next two years and then there was the spectacular downfall.

Allyson was so stressed that she was having novocaine shot into her teeth because she was mashing them at night during that time.  The downfall was in many ways a massive weight off her shoulders.  She went out and had 75 interviews in a month to see if anyone was interested in her.  Her question was consistent to everyone…if you were in my shoes what would you do next?  The common response among women were get a MBA which she found surprising but realized that these women needed outside validation that men did not.

She applied to Columbia, got in and went in thinking it was necessary medicine but discovered she loved it.  She said when she was in the MFA program she would always get hit on by the MBA assholes and now she was one.

After graduating she went to Credit Suisse because many fundraisers easily transitioned into wealth management and she did too but then she got pregnant.  Twenty weeks into her pregnancy she had complications and the doctors order was go home and directly to bed with the order to stay off her feet for the rest of your pregnancy.  She called the team leader wanting to know who she should talk to about working remotely from home.  She heard nothing.  Then she emailed and heard nothing.  She couldn’t believe it.  She had this rocket ship career where she had always excelled and now she was being treated like shit.

Her doctor suggested she email again and cc him on it.  She did and someone from HR finally called her back.  They gave her insurance info to fill out for medical disability.  She was scared and freaked knowing that her career at Credit Suisse was over.  She was home, depressed and couldn’t believe that she was being discriminated against for being pregnant and having to lie on the couch.

Allyson had a healthy baby and four months later she is wondering now what.  She begins to talk to non-profits and charter schools about raising money.  She gets 3 job offers and takes a job at New Leaders which is essentially Teach for America for principals.  She becomes the executive director of major gifts.  A head hunter told her she would be super bored if she wasn’t leading the charge.  She had figured that she had a baby, she did not want to be stressed and wanted to leave the office at 5pm every day.  Within four months she was bored out of her mind. I know that feeling because I did the same thing.  Just because you think that taking a back seat is the best thing to do at one point if you aren’t a back seat person it just doesn’t work.

It was being bored that the idea for Weespring started.  She began to jot down ideas.  Her husband was in business school at the time.  The two of them began to work on Weespring on nights and weekends.  Incorporated and up to her ears in the business she went to the annual business retreat with New Leaders.  She knew she’d never be happy there.  She went back to her hotel room, called her husband and said I have to quit.  She did and two weeks later they were accepted into Techstars.

It was 2013, she raised about $800K for the business.  She wasn’t sure what the model was quite yet and it was really hard to raise anymore money.  After two years of being scrappy and making that cash last the business began to make money.  2016 they were in the black and very mindful about how to build the business without needing to raise more cash.  Allyson is really glad that she raised only from angels.  They allowed her to figure it out.

In 2014 she decides to write the book.  She knows the publishing industry and she wanted to write about something that would help other women who have children during their careers.  As for Credit Suisse, they worked it out but she refused to not tell her story.  Hopefully they learned from their mistakes too.

I’d never count Allyson out.  I love that she figured out Weespring and continues to build the business.  She defines the multiple women who I have watched and invested in…essentially failure is just not an option.