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.

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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.