Moving From a Small Startup to a Bigger Startup

Most of my few readers know by now that I’ve moved on to a new gig as the Content Marketing Manager at Localytics, an app analytics and marketing company.

At 40 people, this is a bigger company than Shareaholic was. I wanted to reflect a little on the experience of working at different sizes of companies, as I’ve now worked at 6-10 person, 40-person and 300-something person companies.


Are We Iterating When We Should Be Pivoting?

I think the unfortunate thing about caring about your job as more than just a job is exactly that: you care. You emotionally feel something for your idea or project that you are working on. When things change or don’t go well, you feel that too.

To be honest, this social business hub thing is a pivot and this is tough. I enjoyed a refreshing moment of clarity going home last week and spending time with my parents. They ask questions like “when is a startup not a startup anymore?” and just recently understood my job thanks to a news piece they watched on Fox News about Charlie Sheen. Far outside of the Boston startup/social media echochamber that I live in, they loved me when I was a waitress and don’t really care what I do when I grow up. I’m enough for them. I think a point of reference is important.

What is a pivot? I hear that word tossed around a lot and I wanted to make sure I was acurately diagnosing my experience. I researched a little and found this inspiring video. In this video, super angel Mike Maples outlines three different pivots he has advised and defines that pivots are not about product iteration, but business model. We’re not adding a couple new features; we’re re-drawing sales funnels, kids.

Yea, this is a pivot.

What does this feel like? I feel like the B2C, UberTwitter-loving Twitter App Store dumped me on prom night. And I loved that app store. It feels like a breakup. Like a Ben & Jerry’s, vodka and chick flicks breakup. I feel like this:

You fall in love with your original idea. You sweat and toil and commit to it. You’re quoted publically about it. You wear the t-shirt. You spend time away from other things, on the weekends holidays and nights, because you are working on this thing. Your passion for this idea re-prioritizes your life.

But then it’s not getting traction, so you have to breakup and make a change. Quickly. I’m not even a founder but I’m…sad. It’s the best way to describe it. (Don’t get me wrong: I actually love what we’re focusing on even more now. I just invested a lot into that original idea, and other people on my team who’ve been here longer even more so.)

I’m learning more about pivots. I found this post on Fred Wilson’s blog about Hashable. Did you know they used to be a company called Tracked? If you scroll down to their CMO’s fantastic comment, you can learn a little more about their process. It sounds like they considered simply focusing on a few good features of Tracked (iterating) but they ultimately chose to completely relaunch as a new site with mobile applications, Hashable. They pivoted.

They focused on finding product/market fit during the concept, alpha and beta stages and then once they had more confidence in their product, began to build buzz. (Although, they were never in “stealth mode.”) Will they be successful? It’s an interesting concept to me, almost like a “CRM for Twitter” in my mind and people seemed to be warming up to it at SXSW. And they have evangelists already. I know how tough it is to build community. I give them huge credit for that.

What I really give them credit for is making the big pivot. The big switch. Digging through research for this blog post I found a ton of Slideshare presentations on “pivot case studies” that to me weren’t about true pivots. They were about product iteration – which is important! I subscribe to the lean startups ideology and think you should iterate and iterate and iterate based on customer feedback until you find that thing that sticks. It’s about perfecting and not perfection. But what I’m wondering is this: How many startups out there are iterating too much? How much time are we wasting iterating on a concept that isn’t getting traction, when you should really make the big jump and target your business model?

I’m talking about mothballing that site you built while you missed your kid’s soccer game and moving onto something else. I’m talking about alienating half of a community you built because they aren’t in your target audience anymore. This is a difficult but necessary choice. I wonder if some startups don’t do this early enough and are left to wonder about the business model that got away.

This is my first startup and like I said, I’m not a founder. I just wish the Twitter App Store and I broke up at homecoming so I could take another business model to prom.

The Career-Girl Manifesto

Computer science Barbie inspires me. She happens to be a girly girl, and happens to like computers too. So that’s how she presents herself. The combination of her intelligence plus her authenticity shows her capacity for effective leadership. She’ll be your boss one day. I’m talking to you, lame startup guy.

Women are told that we need to act more like men to get ahead. We need to downplay our feminine ways and stop sabotaging our careers by doing girly things, like over-explaining ourselves, leaving crappy voicemails and using emoticons in emails. And we can’t cry – that makes guys uncomfortable. And God forbid we make people uncomfortable by being too girly.

But you know what makes people really uncomfortable? Downplaying your girly side. Embrace commanding body language. Be assertive, take charge and leave the emoticons at the door.

You just can’t win. The messages are confusing. They’re telling you you have to act a certain way to garner the respect and trust to earn a high-power position, but you can’t try too hard or else that’s distracting and threatening and people won’t like you. This message is conflicting, frustrating and unproductive, especially for young women like myself who are just starting out in our careers.

Men and women are not equal – we’re different. In Sheryl Sandberg’s TED talk, “Why We Have Too Few Women Leaders”, she diplomatically explains some reasons men get ahead in the workplace and points out some things they do better than us:

  • 57% of men negotiate their first salaries. Only 7% of women do this. (Wonder where the pay gap begins?)
  • Men attribute their success to themselves (“I’m awesome!”) while women attribute their success to external factors (“So and so helped me along the way…”) No one gets a promotion if they don’t think they deserve success!

I like to see behavior differences between myself and my male peers and think about things they do differently (and in my opinion, better) than me. I find the guys I work with to be more direct in how they communicate than I am. They make decisions faster than me. I think that’s because they’re more confident than I am and they don’t waste time second guessing themselves. They take credit for their work. They never seem to feel like people are taking advantage of them, whereas I do. You teach people how to treat you. Is this a difference between men and women in general or just between some assertive guys and a learning-to-be-more-assertive girl? I’m not sure.

While these points are somewhat worth exploring for personal growth I think it’s more worthwhile for young women to identify and cultivate their personal strengths than it is for them to try and act like one of the guys just for the sake of downplaying our feminine sides.

Because honestly, no matter what you do to downplay your feminine side, your gender is still out there. It’s this pulsing theme in the background of your life. No, not all women want to be moms, but the potential and desire for motherhood has a huge impact on your career, the choices you make and the stresses you feel outside the office. Women have miscarriages at the office. Then they go to board meetings. Even the most conservative/prepared/cautious birth control-pill-popping-20-something career girl secretly does a little fist pump and thinks “Yes! Dodged another one!” every month. She doesn’t want kids, she’s focused on her career. She’s in law school or getting her MBA or something. All of this only to end up doing IVF at age 35 and squinting at a pregnancy test every month praying she gets the two pink lines. (Worth noting: 11 of the 12 female Fortune 500 CEO’s are moms.) Even if you do end up on Forbe’s 50 most powerful women in the world list, they’re still gonna list your marital status and the number of children you have. Sure it’s 2011 but we’re still somewhat defined by our ability to reproduce and get hitched, not only culturally but also by the personal choices we have to make along the way. You’re still a woman. It doesn’t matter if you’re wearing a push-up bra or shoulder pads.

I imagine and celebrate a scenario in which an up-and-coming sales exec will go out for manicures to chum up to her female CEO just like how men go golfing with their male bosses. Embrace who you are. I don’t think it needs to be an either-or situation of being taken seriously and being feminine. To encourage more female leadership in tech, it doesn’t need to be a choice between science camp or jewelry. Wear your jewelry to science camp. To get to the corner office, it doesn’t need to be a choice being between an iron-fist or a nurturing hand, it just means choosing a leadership style that reflects who you are.

Furthermore, you’re allowed to hate manicures too. Go smoke cigars with your up-and-coming sales exec if you ladies prefer that. And if you hate jewelry, wear a baseball cap to science camp. Just make sure you are being mentored by your CEO or role model. And get your butt to science camp. Be who you are. I demand this. To be anything else is a distraction from your goals.

I think the article “Can She Lead” offers a good solution:

It seems that authentic leadership is the most important factor women can maintain to rise as leaders for society. Women shouldn’t feel they must lead with an iron fist to thrive because, nor that this is the only way they will ascend the corporate ladder. Leadership should not be garnered by fear, but rather by consensus and a belief in the leader. In addition, women should not feel that they must act passively to conform to traditional ideas of female leadership. Rather, they must be true to themselves and realize their influence as leaders… Female leaders can rise to the top as they embrace their own strengths as women and maintain a leadership style that is embedded in their individuality. This is what will draw others near, inspire, and motivate.

When it comes to female leadership in the workplace, I hope my little blog post is just one piece of an increasing discourse centered around embracing individual strengths. And if we do generalize about differences between men versus women, I hope we see more conversation that emphasizes the benefits of a “female style” of leadership. Positive reinforcement, people: Let’s talk about what we’re doing right once in a while!

We’ve got a ton of work to do. 85% of PR practitioners are women but the top 80% of management is male. The glass ceiling still exists in many industries. I’m painting my nails and I’m getting a hammer.

How to: Be a Startup Kid

Considering a job at a startup? New to startup life? Based off of my extensive eight months of experience, here are my tips:

1. Be Agile

Take your job description. Print it out. Burn it. Be ready to wear many hats. Depending on the direction your company takes you may need to take on different projects or tasks that you didn’t initially set out for. Be flexible, learn as you go and multi-task.

2. Be Decisive

Make decisions quickly. Be really confident in your choices, knowing that usually things can be iterated on and re-considered later. Act quickly and trust yourself. Second-guessing wastes time you don’t have.

3. Drink

Chill with other startup kids. Mingle. Go to events. Startup friends understand your work life in a way that others usually don’t. They’ll be able to offer really great feedback and advice, and some of the best networking opportunities come from just hanging out. True story: I met my friend who I hired as a freelance blogger when we were just hanging out drinking wine with other startup geeks once. Networking doesn’t just happen at conferences.

4. Drop the Perfectionism

You do not have time to nit-pick over minute details that don’t move the needle. Some jobs are extremely detail-oriented and are totally focused on shipping only the most perfect product or document possible. At a startup it’s less about being perfect and more about perfecting as you go along. “Ship it and change it based on customer feedback”  or “let’s test this and see if it gets traction” are more the themes at a startup.

5. Get Over the Rainbows and Butterflies

Your bad ideas that you love so much but just don’t work? Love ’em and leave ’em. You can’t get emotionally tied to and hung up on specific ideas or projects at a startup. Test your idea, measure the results and be ready to scrap the whole thing and move onto the next one if it wasn’t the right solution.

6. Play Ping Pong. Wear a Hoodie.

Be the type of person who gets bored with the mundane and thrives under pressure. Learn to be happy despite a strong level of uncertainty. Show up at work and get stressed. Then, when you need to relax a little, play ping pong or something. Startups are nuts and being able to keep an even keel – in whatever way you do that – is key.

7. Know Your Needs

Feeling sick? Need a day off? This one’s tough for me too. Part of what makes you a successful startup kid is knowing your needs and taking care of yourself. If you need more sleep, sleep. You need exercise and a diet that doesn’t only consist of PBJ & PBR. When you take care of yourself you help your team by making sure their engineer or product person or marketing person is ok. Know your needs and take care of them.

8. Choose Your Choices

Not everyone is going to “get” the startup thing. They don’t understand how your job isn’t just a job to you or why you’d want to work such crazy hours or do what you do. Get behind your own life choices and commit to your own decisions. Then, it really won’t matter to you who does or doesn’t understand or approve. They’re your choices and you want them, after all, so who cares.

9. Be Hungry

Be hungry to learn. Be hungry to figure it out. Be hungry to find someone who already knows how it’s done and then go ask them how it’s done. Identify your weaknesses and seek the knowledge or experience that fixes them. You’ll likely be “punching above your weight class” and will be challenged with a lot more responsibility than you initially thought. If you are absolutely die-hard hungry to learn all you can, succeed in your own role and make your contribution to the team a success, that’ll be ok.


Execute like a ___ ___. There is a unique level of productivity and motivation needed (demanded) from each member of a small team. It’s beyond the level of just getting to the bottom of a to-do list, it’s about asking “What’s next?” and being able to immediately act on that feedback. It’s about bringing new ideas to the table, asking questions, giving your input to every part of what’s going on. Showing up isn’t good enough, and participating isn’t intense enough either. This is about being really involved and applying your expertise to each aspect of your new business.

Startups are crazy, but somehow I love this. What other qualities or tips would you add to the list?

“Eternal Champion of the Entrepreneur”

I'm re-posting this article from TechCrunch because one of my top goals in life is to chase my crazy daydreams. Because at one point, Twitter was somebody's crazy daydream and Michael Arrington said that was stupid. At one point, somebody thought selling shoes online wouldn't work. But somebody kept pursuing that and we have Zappos. And even if it wasn't a company, maybe it was another idea. Maybe somebody thought the OldSpice social media campaign was a bad idea or that no one would buy iPads.

In my humble opinion the world is not lacking raised eyebrows, devil's advocates and skeptics–although they are most certainly necessary. But I think we really need more of those innovative brainstormers with the thick skin to relentlessly pursue their ideas.

I often point to my first post on Twitter, the day it launched in 2006. Why? Mostly because of how wrong I was. Best line: “I imagine most users are not going to want to have all of their Twttr messages published on a public website.” I also love that original vowel-free logo.

The first couple of comments to that post are classic as well:

I do not understand the utility of adding the SMS messages to a public webpage or making messages from my network public. I would have to pass on that type of offering. The ability to make messages private should be added asap.


i do not want to be woken up at 4 a.m. because my friend got drunk and decided to text Twttr with “asdl im at barasdf sooo drunksalkfjs”…i find it interesting such an annoying feature is supposedly causing viral growth…i’m done developing social software if the key to success is to be intrusive


So is it pronounced twitter or twatter?

With the benefit of hindsight it’s clear that I was…a bit off on how Twitter would play out. As were most of the commenters, although commenters are often negative just to be negative. And the most wrong of all? The Odeo investors who elected to take their money back rather than port it over to Twitter.

My point here is that you never know which startups will make it and which won’t. As a blogger I say it like I see it, but I’m wrong a lot. It’s why I’m not a venture capitalist, where wrong decisions tend to have real consequences. And this is also a reason for us all to give startups a little breathing room when they’re finding their space in the world. Startups evolve. The world evolves (things have changed a lot since 2006).

That dumb startup that’s just a rehash of that other thing from before, with a twist, just may turn out to be something special. Perhaps world-changing special. It’s why I like The Man In The Arenaso much, and why I’m an eternal champion of the entrepreneur.

Good communication = simple and emotionless email

They say you can’t shit where you eat. It’s a common phrase used as advice of why you shouldn’t mix dating with your career. But as I skip and run and tweet and yes, sometimes stumble along in my twenties I’ve seen so many similarities between the two, but that’s really for another blog post. Or a memoir. A collection of essays. I’ll crowd-source it.

Here’s the thing: In perfect relationships, the same “they” who speak of shitting and eating (sitcom writers I suppose) also say that when you fight, you fight perfectly. I can live to say that this is possible in the workplace. You disagree perfectly. You communicate perfectly.

I love my team because of our email style and because of our communication over all.

If someone doesn’t like my idea, they say so. An email is signed:



If we are deciding to discuss at another time, that might be phrased:

Taking this offline.


If someone wants detail, they ask: 

Can you explain this further?


How so?



It’s direct. It’s emotionless. Emoticons are few and far between. Exclamation points are rare. 

I’m not on a roller coaster. I’m not going from winky faces and a Thanks!!! at the end to a sudden Regards when all of the sudden someone decides to get serious.

If someone disagrees with me, they say so. We hash it out, typing away with our headphones on sitting three feet away from each other never once looking up. It stays on topic. It’s always about the product, the newsletter copy or the blog post. I know it’s not about me as a person. What freedom! I can say what I think. They won’t take it personally, because it isn’t personal. It’s just an email.

Disagreement or consensus, either way the email exchange will probably end with a period. We look up and go to lunch. There, sitting face-to-face we can enjoy each other’s real smiles–not emoticons, our real excitement–not exclamation points, our real laughter–not our lol’s.

That’s because emotions and personalities are better felt, communicated and appreciated outside of a context with such brevity and oversimplification. 

But that’s the thing. It’s email. Why not keep it simple? Free yourself and your co-workers to actually get things done, get decisions made and do things efficiently without having to second guess the hidden meaning behind that signature or mood in that greeting.