Jessica Jackley: Being a Happy & Successful Founder/CEO/Mom

Transcript follows & video below 

This interview was generated after Paige Craig published a post Putting Women First about his thoughts investing in a pregnant Jessica. Jessica’s response & comment was inspirational for me.  Jessica had just found out she is pregnant with twin boys when I interviewed her.

I guess I just want to acknowledge you really because I just found that the comment that you put on Paige’s post was just really awe inspiring. That’s what made me want to reach out & interview you. I’ve been interviewing vcs, angels & women about the shortfall in funding for women. Adeo Ressi from made a really salient point. He said that

The startup culture was actually created by men & the only way that we are really going to encourage more women into being entrepreneurs, having startups & going for funding, is actually to change the culture. I just thought Wow, no-one’s said that but it’s actually so the truth because you have to be manic.

Adeo Ressi

I have to make sure that I read that.

Jessica Jackley

I’ll actually send you the link. But it impressed a lot of us when I posted it. I thought it was really spot on because you have to be really insane to be an entrepreneur these days, the workload. So that’s what really spoke to me & I just wanted to read your comment for people that possibly hadn’t seen it.

I know that Paige said:

“A pregnant founder / CEO is going to fail her company”) that popped up in his head, I’m glad he asked the specific question he did – specifically: “…how in the hell is this founder* going to lead a team, build a company and change the world for these businesses carrying a kid around for the next few months and then caring for the kids after?”

Paige Craig

And your response:

There’s another aspect of this conversation about a founder of a company to have the goal of achieving balance at all when in start-up mode, and I’d like to address that too. Do I work long hours? Weekends? Of course. Pull all-nighters when needed? Sure. But working until I fall asleep on my laptop and doing nothing else on a regular basis makes me less effective. Turns out that getting at least a little sleep, exercising regularly, having healthy relationships outside of work, spending time with my family, reading a book for fun now and then, etc. makes me a better Founder/CEO.
The next paragraph I really loved: In fact, this isn’t just how I run my life, but it’s how my cofounder Dana and I run our company. We created ProFounder with the intention of shaping a healthier – and more efficacious – culture that gives everyone on our team the opportunity to be a full person, not just a cog in a machine. We not only encourage but celebrate each other’s victories in and beyond work.  At our last team retreat, we reported our proudest moments personally and professionally; on the personal side of things, every single individual shared some detail about how the most important relationships in their lives had become better since they began working at ProFounder. This model is working. Business is thriving. We are flourishing. And we’re trying to give every entrepreneur we work with through the ProFounder platform the same options for their own endeavors, starting with the chance to include investors who care about them as human beings – who are invested not just in their business but in them as people.
The last paragraph that really spoke to me: I have no desire to fit that old stereotype. I desire to live a life that is rich in relationships both in and outside of work. I desire to reap the many different rewards that are abundant in my job, working in this incredible start-up every day. I want to surround myself with a team, including investors, that challenges me and helps make me better. I want to live my life transparently, and if being a happy, successful Founder/CEO/Mom serves as a helpful example to anyone who wants to use me as such, great

Jessica Jackley

Well you’re definitely a role model for me!

Thank you for saying that, it means a lot. You’ve already been down this path but that means a lot to me!

Jessica Jackley

Yeah I’ve been down this path, but I have to say I was much more driven. So I’m going to put my hand up for that! I wondered if you could just talk to me about your past history sourcing venture capital & how it’s been for you as a woman?

I’ll tell you this, with Kiva, the company I started before Profounder, it was really interesting because I got to interact with everyone as a donor in terms of high net worth individuals who helped fund Kiva’s operations. Or I spoke with people as lenders & really I should have flipped that. First & foremost everyone can be a lender, right? So that’s how I interacted with everyone & that lending relationship, I have a lot to say about that. How to promote the connection of equality, the connection of dignity & respect as the business partner not that traditional donor/beneficiary power thing that can happen. That’s the first level but then with a lot of folks in Silicon Valley that did serve as also serve as professional investors, maybe they’re vcs, I often interacted with them as volunteers through Kiva’s board. Or as advisors or donors for the organization which again was a non profit. What was interesting about that experience & I think feeds into how I’ve interacted with our funders now for ProFounder which are a collection of more than 30 friends, family, community members, angels, some professional venture capitalists as well.
So I interacted with donors in a charitable way for them to contribute financially. The focus was about the social return, that’s just what it’s about. So I think that served me well & it served Dana & I well in interacting with our investors because they’ve self selected & we’ve chosen them. We’ve said no to some very major funders because we didn’t think that there was a cultural fit. Lots of money on the line there! We really wanted to include people who believed in the vision & who want the mission of what we’re trying to do that they’re committed to that. When you look at our funders (& I know your question was what is it like as a woman to interact) so part of it is, I know I can speak about our specific experience & I am a woman so this will be at least one data point, how’s that? I know for me the social part of it & the idea of the big picture change for the world that we want to cause is always front & center in this, always part of the story. Yes by the way, & it’s not by the way, it’s central we don’t want to be intellectually lazy about it & not have a robust, strong, scalable, profitable institution. By the way I find it funny coming in a very non-traditional order of things like doing non-profits first & then doing a for profit, you have to reiterate over & over again ‘No, no, no I mean profitable even though Kiva at many points & will be in the future a sustainable organization. It’s the same concept it’s just a different word right? I think that that’s been really helpful to us & I think perhaps that is more of a natural fit as a woman leader. It feels very much like a natural fit for me to talk about the story, to talk about the point of all this & then get into the structure of the business & why it’s a great business model, our revenue, how we’re going to make money, that sort of thing. Our collection of funders now is awesome. We really wanted to prove not only that crowd funding could be done but that it has value above & beyond just actually getting the funding that you need. We have true friends & family investors in our company right now, all the way up to the lead funder in the first round. We’ve raised a total of $1.3m so far. We’re actually still wrapping up a bridge round but in the lead round a third of it was taken by Kapor Capital Mitch & Frieda Kapor & Stephen DeBerry on their team, are true advocates in so many ways for women entrepreneurs. Frieda Klein is just a phenomenal woman, I could do a whole interview just about her. Her background is just incredible. So we felt really good about that fit. So far my experience has been, I think I’ve been using the same values, the same framework, a lot of the same language that I’ve always used & always will use. I don’t want to fit stereotypes & I’m not trying to fit anyone else’s model per se. Dana & I are just trying to do what we want to do in the world & I think naturally we are 2 women who believe in the same things & believe in the same change that we want to see. It comes out as the whole package, when you invest with us, when you partner with us in that way, we really believe it’s partnership. We really engage our investors a lot & they’re ready for that which is great. We’re not just talking about here’s the money you’re going to get back. We’re talking about here’s the thing that we’re going to go do together in the world.

Jessica Jackley

I really like the idea that you’re focused on finding a great fit with an investor. That’s a baton that I’ve been waving around a lot, is that you really do have to find a good match with an investor & I talk about the chemistry between investors & founders. In the course of trying to find those funders did you come across any bias or any challenges in being a woman approaching investors at all?

Well it’s so funny, I don’t know if you can see the gears turning but I’m trying to think what to quote anonymously. We almost thought at one point, oh my god we need to start an anonomyous blog about all the things that were happening. Let me screen what is appropriate. The short answer is yes. I generally believe that everyone’s out there doing their best & doesn’t have bad intentions. So when people offend or put their foot in the mouth or something, it’s good not to be reactionary & so offended that you just sort of fight back with something but to use it as a chance to get on the same page with someone & tell them what you believe & why you would see the world differently than what they just did or something like that. I think a lot of people just get angry & stomp out & cut things off. If & when you can have an ongoing dialogue then that’s the thing, keep the dialogue going. This is why I was so excited to have that conversation out in the world, publicly with Paige, one of our investors. The dialogue itself is the thing. Yes we’ve had some interesting struggles & interesting comments to us. We’ve been asked out. We’ve had the flippant comments here & there about being women. One funder who we’re not working with, made a comment about that he was worried about future funding (even though he wouldn’t do this) conversations going down a different path & us being hit on by other funders. It was just such a strange sort of cop out for it. But again in general it’s a big wide world out there & there are a lot of people. Even though you might be sitting across the table from someone who doesn’t look like you, is not the same gender as you, I feel like i learn all the time from men who themselves would fit that old stereotype funders entrepreneurs & teach me about how to treat people the right way. I have absolutely had mostly a positive experience. I wish selfishly that there were more people that looked like me. I sometimes when I give lectures & I talk about both Kiva & Profounder & entrepreneurship overall I have a slide that’s supposed to be funny. I’m not a comedian but it’s a picture of the Madmen cast actually & it’s about men in suits & I talk about how a lot of the traditional funding world doesn’t look like me. I’m not wearing a suit, I’m not a guy, what does that mean. it would be nice to encounter more women. I think in about 70 plus meetings with investors, we actually only met with 2 who were women as we were raising our seed & our bridge rounds. It would have been nice to talk to more women. But we’re going to make that happen.

Jessica Jackley

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