8 Startup Lessons You Could Learn from Gotham Gal

Posted on Apr 16, 2011 | 27 comments

8 Startup Lessons You Could Learn from Gotham Gal

It’s easy to think that the wife of a well-known & successful VC (Fred Wilson) would have had an easy and storied life of wealth and privilege. I had previously had the opportunity to spend time with Joanne Wilson, Fred’s wife, and knew otherwise.

That’s why I was so interested in having “The Gotham Gal” come on This Week in VC (video link on YouTube, download iTunes, episode 15)) and dispel those myths. In fact, as she tells it, in their early career when Fred was young in VC, Joanne was earning 3x more money. Well into their 30’s “they were living paycheck-to-paycheck” as Joanne had taken time off of work to raise three children.

After college Joanne worked for 4 years in retail apparel at Macy’s where she initially managed sales reps on the floor and then worked as a buyer of clothing. After 4 years of retail she went to “the other side of the business” working for a clothing brand where she sold apparel to department stores and other companies. This is where she first developed sales skills.

She doubled her salary by going into sales. Then after a year she got into the business side and learned how to manufacture, what the margins of the business were, etc.  She left there to join a man running a clothing brand. She came in and took over the business. In 18 months from $1.5m to $12m in sales. She did this because she had great rapport with buyers. She knew their business needs because she had been on both sides of the business.

Below is a nice summary of our interview with some great quotes from Joanne. I think this video should serve as an inspiration to any young aspiring female entrepreneur (and male!) and is worth watching when you have a few moments.

But for everybody else, where are 6 things you could learn from Joanne Wilson:

Sales: until about minute 20

1. Get out of your comfort zone – don’t just work on the things you know how to do or like doing “People tend to gravitate toward areas that they know. Totally get outside your comfort zone. Put yourself in a position to learn things you don’t know” We talked about this in the context of management (in retail her motto was, “get away from the cosmetics department. You already know that”), in sales and more broadly as an entrepreneur.

2. To be effective at sales you need to really understand the business of the person who will buy your product. “[I was effective at sales because] I understood their business. Most people who worked in the business didn’t know how to make a profit & loss. I provided information for my customers to make their lives easier.” Really understanding the business of your customer matters. It’s the key to growing a successful business and is a theme the Steve Blank plays up a lot. I agree whole heartedly. The other money quote she gave that I loved was, “”Totally get out of your office.” Sounds kind of obvious. Not enough entrepreneurs dedicate enough of their day to this.

3. In sales you also need to establish rapport, ask insightful questions & then shut your mouth! “A lot of sales is innate. A really good sales person can get people excited and get people to tell you information they won’t tell other people. Build rapport in whatever way you can. Who knows, it could be fishing or whatever.  Say very little. The less you say, the more the person on the other side gives you back. As a sales person, just ask the right questions and you’ll get the answers you need.”

4. Be a mensch – the world is small than you think and bad karma will catch up to you “We’re in a very small community. Life is too short to be a dick.” There’s no reason to be nasty to your competitors or mud sling. There’s no need to bad-mouth other people. It’s surprising how small the tech community is and the older you get the more you realize how much people from earlier in your life have a way of coming back into it. Be a mensch.

On being a woman, becoming a mom & forming a sense of identity [20-45 ]

5. For women – “Don’t get off the train completely when you have children. You need to keep your skills. You need to keep your database in terms of connections and the people you know. You need to keep your relationships up.”

“When I stopped working it was quite a shock to our system. Even if you continue working, you’re still responsible for [your kids well being]. I didn’t think about who was going to put food in the refrigerator.”

“The Internet saved my life. I needed something to find my own identity.” She went to work running sales for Jason Calacanis at Silicon Alley Reporter (mid 90’s). The Internet really re-connected Joanne with her former working self.

Invested in “Catchafire,” which is a business that helps people (mostly women) connect with pro bono opportunities where they can put their skills to use. Take a little break but keep your skills fresh.

“There are so many places you can go on the Net where you can find your community. I would tell women to find them.”

6. The current generation of college students want to be entrepreneurs more than rock stars – “This next generation is going to be very interesting. After seeing “The Social Network” there is an increased attitude amongst this generation (of women) that … why not go into startups? They all want to be entrepreneurs – they don’t want to be rock stars.”

7. To run an effective business it’s really important to hire women in your company & as advisors – “Men tend to pump up their chests more (than women). I think it’s really important (to hire women). Women take a look at things differently. They understand things differently. Make sure they’re on your board, your board of advisors, whatever. Make sure 50% of the people you hire are women. The women are out there.

Certainly if you look at eCommerce & social media – women are the ones using these products. What better to have on your team than someone who understands this at a fundamental level.”

8. Women need to start becoming entrepreneurs at a younger age – “Don’t go to work for big companies, don’t get an MBA, go to work for a startup and start on this path. Start early. In the next generation everybody (including women (are going to write code).”

“The majority of businesses that I’ve been investing in lately are ‘women businesses.’

You can watch it all on YouTube or download from iTunes for free.

  • http://www.6tiers.com 6tiers

    ‘To run an effective business it’s really important to hire women in your company & as advisors’

    Great comment. I believe good decisions are when a diverse set of people from different backgrounds come together to analyze a problem thoroughly and present a solution. So if you want your business to succeed, have diversity (women/minority) in your work place. This is one way to ensure good decisions will be made more often than not.

  • http://www.facebook.com/profile.php?id=689987025 Jebb Dykstra

    Great lessons and advice from Gotham Gal. Thank you Mark for breaking out the video in bite-size chunks.

  • http://twitter.com/jw512 Jason Wesbecher

    15 years wasted in my comfort zone. Going to start living in public. I launched a blog tonight, thanks in small part to my passive observation of this community. Thanks for the inspiration. (the blog is http://www.lingonomics.com).

  • http://twitter.com/tientown Barbara Tien

    Awesome interview, thank you. I believe the author you referred to about the differences in speaking styles between men and women was Deborah Tannen, she’s a linguistics professor at Georgetown and the book was her best selling “You Just Don’t Understand:
    Women and Men in Conversation” from several years ago. (http://www9.georgetown.edu/faculty/tannend/)

    For many years women in business, and tech in particular struggled to, rise to Henry Higgins challenge and “be more like a man.” (http://www.stlyrics.com/lyrics/myfairlady/ahymntohim.htm)

    Joanne Wilson, in your gracious interview, highlights why it’s better for all of us that women aren’t more like men. Cheers!

  • http://hirethoughts.blogspot.com Donna Brewington White

    Great interview, Mark! Thank you.

    I say that the more we can hear from Joanne Wilson, the better. One of the things that makes GG such a very interesting person is the multifaceted perspective she brings given her various roles and vantage points and her ability to meaningfully process this.

    It continues to be extremely interesting to hear about how women with children manage what is often a much more complex career strategy and life cycle. I am a firm believer that it does not have to be kids OR career, although just like with the concept of “having it all” you can’t always have it all at once.

    I found it interesting (and encouraging) that you encourage startup teams to ensure that women are hired early on to round out the team. When you intentionally hire outside of what may come more naturally, a more perceptive and even nuanced approach to recruiting and hiring may be required (or at least it may “feel” more nuanced) — and without a lot of experience in hiring, this is more difficult. While I own that this is a generalization, I find that people who are hiring often go for the most straightforward and obvious fit which does not always result in hiring the best person for the job or in a more “diverse” team.

    I would be VERY interested in a post from you that addresses how you would encourage startups to go about hiring women — creating more diversity on the team while at the same time hiring the best person for the job. Because of course we want the latter, right?

  • Ella Dyer

    Thank you Joanne, your candid conversation has given us much to think about. Please join us at StartupChicks.net and see how we’re following your suggestions.
    All the best,

  • http://twitter.com/rrohan189 rrohan189

    Thanks Mark – I really like the summary format. Thanks for sharing!

  • http://bothsidesofthetable.com msuster

    Totally agree because it’s seldom that our customer bases are devoid of women! Plus, even if they were, as Joanne points out – women look at the world differently. Why not mix that perspective into the pot?

  • http://bothsidesofthetable.com msuster

    Thanks. Make sure to watch it when you get time. She gives better advice than my summary notes! 😉

  • http://bothsidesofthetable.com msuster

    Awesome, Jason. The key to blogging is to be sure that you a) keep the content coming and b) promote it to gain an active following. Increasingly people are blogging into social environments like Tumblr. That might help, too.

    Plus, your travel hacks might make for great articles so you probably have about 40 posts just in the comments in your side notes! Make sure to atomize your posts to get more production.

  • http://bothsidesofthetable.com msuster

    That’s exactly the book. It changed me. It gave me a perspective into the differences in how women & men think that has stood the test of time in personal and work relationships. I recommend it to anybody.

  • http://bothsidesofthetable.com msuster

    Thanks for writing. It was nice to hear lessons from the GG. I wanted to reinforce the idea to other women that many successful men have wives who were equally (or more) successful wives pre-family (and post family, too!). My wife is one of those.

    re: hiring women in startups – I will address at some point. Right now it’s a bit too personal to the companies I’m working with but with the passage of time I can talk about it a bit more.

  • http://bothsidesofthetable.com msuster

    Thanks for writing. It was nice to hear lessons from the GG. I wanted to reinforce the idea to other women that many successful men have wives who were equally (or more) successful wives pre-family (and post family, too!). My wife is one of those.

    re: hiring women in startups – I will address at some point. Right now it’s a bit too personal to the companies I’m working with but with the passage of time I can talk about it a bit more.

  • http://www.6tiers.com 6tiers

    ‘Why not mix that perspective into the pot?’

    This ‘luxury of bias’ may not be sustainable anymore. ‘Why not women’ is slowly gravitating towards ‘We need women’. Women in business is no more ‘a nice to do’…present day its all about wining. The company that has a better mix will have a better chance of success.

    The problem with any one-dimensional team (could be all male or all female or other) is group-think occurs. Not necessarily a bad thing if you’re a boss but you might just miss a perspective that makes for a well-rounded decision.

  • http://twitter.com/mariawv Maria Wich-Vila

    Thank you so much for this – not just for the great interview overall, but also for the mention of CatchAFire – I hadn’t heard of it before, and I just signed up (even though I’m in LA, not NYC, but…)

    Several companies out there are trying to do part-time job-matching for moms, but I spoke with the founder of one and she said that it’s surprisingly difficult to steer big companies away from the “100 hours a week, 100% of those hours in an office” paradigm. This seemed ridiculously illogical to me at the time, but I’ve seen first-hand now that it’s true. Until companies open their eyes and become more flexible in their thinking, they’re missing out on a great opportunity…and both parties lose. (some of the mommy-track jobs at big companies are a good start, but they do tend to relegate bright women to dead-end dungeons like “training”)

    Hopefully the silver lining of this frustrating situation is that more moms (in addition to recent grads) will start founding businesses and creating their own opportunities…though ideally we’d have more choices!

  • http://www.gothamgal.com Gotham Gal

    thanks mark. it was so great to speak with you. the conversation we had rarely takes place in the day to day world of the tech industry. i hope to have more of them!

  • http://www.twitter.com/gcsf Gary Chou

    Jason, great to see you going public.

  • http://notesfromtheninjabunny.tumblr.com/ Emily Merkle

    Mark – thanks for sharing; Joanne – great insight, and thank you for promoting women in business. All too often I’ve been told – by female entrepreneurs like myself – (and I’m 36) – you “look too young/won’t be taken seriously by male C-level”…to – you’re too blonde/too aggressive/too strident/have too strong a personality…women are NOT respected in this industry – even female-run operations – and it is beyond insulting.

    Joanne, keep on keeping on…if I can be of any help, I’m in.

  • Dave W Baldwin

    FWIW… Emily, the early 30’s thing hits both genders. My son just turned 34 and I had to mentor him when he was 31-32. That’s the age where you have an idea to improve results (profit) but not listened to because you’re considered a kid.

    Then you have to be careful because you just do the deed, get noticed by the upper echelon and then have to perform miracles as the other deadbeats try to bite your flesh.

    Just pay attention to what the older/experienced bunch are missing out on (including their own age demo) and fill the need with your sweat. The biggest lesson we learn is via the safe haven we end up killing ourselves to fill the pocket of someone else, becoming a stat.

  • Dave W Baldwin

    Good interview. There is big opportunity out there due to the needs of gals who are trying to do the job, the kids, the everything that can be thrown at you after school thing and so on.

    If you are designing a product, make it useful for the female. They control the $$ in the household. Their time is precious and will be open to a gadget helping in their organization of life.

  • Kim Straub


    Glad I listened to the whole interview and not just read the summary because I would have missed the shout out you gave me at the end! As the “lady” who came up to you last week at NYU, I’m taking your advice and taking just an hour at least 5 days a week to focus on code. It’s nice to know what is practical for my schedule still “counts.” That question I asked you came from reading somewhere that you can’t be a “specialist” if you’re going to launch a company. I think I interpreted that as needing to know everything halfway decently before I made the leap, which, as an outsider to this industry, would take forever. At some point you’ve got to just “do” and tell yourself you’ve learned enough to get by. And for me, that’s focusing on what I do best–all the outward-facing stuff–and taking an hour or two each day to “dabble” in one of the areas outside my comfort zone.

    So great to see Joanne talk about her talent for sales, and give that skill set the credit it deserves. I was telling you how there’s this notion circulating around that being “the business guy” isn’t good enough and that you need to make yourself over into “a product guy,” if, you know, marketing, sales, customer acquisition, biz dev, and pr is “all” that you’re good at. That’s some seriously flawed thinking in that, I’m realizing, and needs to be addressed. We might be scaring off a lot of women who, like myself, bring those skills to the table and think there’s no room for another “business guy/gal.”

  • Mstengel

    Great article and love her comments. I’m a female entrepreneur myself, started in college a couple years ago with 3 other women and are trying to grow. Is there any way to get in touch with her? I always love getting advice/help!

  • http://bestresearchpaper.com/ research papers

    thanks from me too))) usually i dont like things of that kind but this time i liked it)

  • LaVonne Reimer

    Mark, I appreciate all your posts, especially the way you continue the dialog via comments. This one appealed to me for many of the same reasons already covered but point #2 brought back a memory. I’m now a lawyer who has firmly turned entrepreneur but back when I first started practicing law I couldn’t understand why my partners were always summoning clients to our 20th floor offices. It made so much more sense to me to go and see them in their environment. Understand why they started their company and how they thought about it. That’s what I did. I just thought of it as being a better lawyer. Looking back on it now I can’t say whether it was a female perspective or not but it surely was the beginning of the end of my career as a lawyer. The business side just seemed so much more interesting! Thanks again for another inspiring post.

  • http://academia-research.com/ essay jobs

    Useful post. Thanks for it.

  • http://www.prudentcloud.com Subraya Mallya

    Great insights around sales for Gotham Gal. As for amount of talking by sales guys – I had this line (that I borrowed from some book I read) for my sales guys – we have two years and one mouth – so listening should be twice as much as your talk. It is so true. Another one I used to tell sales guys was – be a doctor and not an auctioneer. As you can imagine coming from a techie guy – sales guys did not appreciate it as much :)

  • http://notesfromtheninjabunny.tumblr.com/ Emily Merkle

    Well – you know – I’ve proven that I can generate revenue with my strategies. I am 36 – been in 12 years. I do not worry about deadbeats – I do not work for large bureaucratic companies. Deadbeats wash out. I’ve sweated enough. I am tired of – as you say – filling other people’s pockets while they lord about. I will not stand for it. But I do not know how to break through. I look young – say 28. I am reasonably attractive. I am running into gender discrimination. I feel sometimes I intimidate men….??