Meet DreamGirl Sarah Milstein: CEO of Lean Start-up Productions

22Sarah is thoughtful and witty. I met her at Blogging While Brown. She led an informative and inspiring presentation on how to become a professional speaker. I was able to grab a few minutes with her after her presentation and she was equally as endearing as when on stage. A HUGE plus and definitely a marker of being a badass DreamGirl.

What do you do and why is it important?
The company I run, Lean Startup Productions, teaches people to build and scale high-risk startups. In everything we create—conferences, training workshops, articles, webcasts—we seek to demystify the mechanics of entrepreneurship and to show many types of people as entrepreneurs. Our goal is to help democratize entrepreneurship, making it more accessible and more successful for a broad range of people.

What advice would you give to your 20 year-old self?
Get more sleep. Seriously. In my 20s, I stinted on sleep, and in retrospect, I think I was less happy and less productive as a result. I’m a night person, I’ve now structured my life such that don’t have to wake up super-early most days. It’s paying off.

What are three things that you know for sure?
1. Scheduling time with family and friends is a long-term investment in your own happiness. 2. In the US, our education, health and criminal justice systems all need complete overhauls. 3. It’s a good idea to keep a lot of chocolate chips in the freezer in case you need a quick sweet snack.

What is the best advice (financial, emotional, spiritual, health-related) that you have ever received? Why did that piece of wisdom resonate with you so much?
I wish I had received a piece of advice that I could say has guided me over time, but honestly, I either haven’t received such wisdom or I haven’t taken it in. At different times in my life, different things have resonated.

What is going on in your business/career that EVERYONE should know about now?
Is there a product or services that we should ALL know about? Later this summer, my company is going to roll out a site that I’m pretty excited about. But there’s nothing to see yet! Right now, our flagship conference—designed to help entrepreneurs learn from each other–is coming together. It’s been very popular in the past, but I believe that this year we’re really going raise the quality of the sessions and increase attendees’ opportunities to meet other relevant people. We have a reputation (well deserved) for bringing to the stage women and people of color who are terrific speakers with great advice to share; this year, we’ll continue that work and do more to make sure that people often under-represented at business conferences as attendees can join us, too.

What makes you a DreamGirl?
I’ve learned that I don’t really like working in corporate environments or even in established non-profit organizations for long periods. So I’ve forged a career that has let me work in other ways. It’s not as obvious how to go about building your worklife when you want to do something unconventional, and it’s taken a while to line up my skills and interests and opportunities. But I’m now running a startup that I care about, and I draw a salary, and I get to try new rules for work (like no email after 7p; see below).

What rituals, if any, do you do on a daily, monthly, or yearly to keep you focused, positive, or centered?
My company has a rule that you don’t send email after 7p in whatever timezone you’re working in or on the weekends (you can work as late as you want, but then you have to queue up email to send the next day). Though I occasionally have to work nights or weekends, that rule really helps me focus during the day and take breaks from work reliably—which then makes me more effective during the day.

How do you handle setbacks? What skills, support, or personality trait do you rely on the most to help you overcome adversity?

At Lean Startup Productions, we tend to think in terms of opportunities for “continuous improvement,” which I find a useful and motivating way to frame glitches and disappointments. When I have to play through significant challenges, I tend to process those with my life partner (who’s also an entrepreneur), a couple of close friends and/or an executive coach that I work with. I wouldn’t say that I have a personality trait that’s particularly useful in these situations, but I have found that as I’ve gotten older, I’ve gotten a lot better at learning from adversity and keeping it in perspective. I’ve also gotten better at those things as I’ve gotten more sleep!

Sarah Milstein is CEO and co-founder of Lean Startup Productions, a media company that teaches people how to build and scale high-risk startups. She is also co-author of The Twitter Book, and she writes regularly about race, gender and merit-based decision making. Previously, she was a regular freelance contributor to The New York Times, among other outlets; she founded Just Food’s CSA in NYC program; and she helped children’s musician Laurie Berkner launch her record label. She splits her time between New York and San Francisco. Bonus fact: She was the 21st user of Twitter.
@SarahM
Blog: http://dogsandshoes.com

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