21 Lessons Learned in 21 Weeks at a Startup

I’ve been selling/marketing/customer support-ing at isocket for 21 weeks now and can’t believe how much stuff has happened. We brought on lots more customers, lost a few along the way, pushed out new features, did lots of bug fixes and did a lot of stuff in general. I’ve learned tons more since I did that post on learnings from the first few weeks, so I figure now is as good a time as any to share new findings. Here goes.

1) Headlines > Content for email marketing

When first starting with email marketing, I think many people obsess over their email content for a high click-through rate. This is wise but only if equal (or even more) time is spent on the headline. If they don’t open the email, it won’t matter how good the content inside is.

2) Don’t let things fall through the cracks – use a system

There are so many things to do and so little time to do it all. John, our Founder/CEO is really good at keeping track of people to follow up with Highrise – and it’s something I need to get better at. What are you using to make sure critical things don’t slip?

3) A little personal touch goes a long way

My coworker Hup is great at adding that personal touch to everything he does. A funny link on a company blog post. A joke in the middle of a phone call. A surprise package. This is the stuff that’s allowed us to retain such a loyal customer base even when our product was FAR from perfect.

4) You are never going fast enough

I look back and realize that so much has happened since I started at isocket, and yet everyday I think “Damn, I can’t believe the day is over. There’s so much more I want to do.” You are perpetually time-pressed when you work at a startup.

5) Almost every startup person has a side project

Both within my company and with the folks I’ve met in the community, it seems like everyone has a side project. I remember meeting Hanah Rose from a Tech Nobody and how she thought she wouldn’t be a legit startup person until she had her own side project. Interesting outside perspective.

6) People are often more humble than their blog suggests

At some point Dave McClure came into the office – he’s an investor and advisor for isocket and has posted some pretty vitriolic stuff (eg”Hurry up and Die, U Pathetic Dinosaurs“) But he was actually a really thoughtful and (dare I say it) nice guy in person. I feel like there are many others people aren’t as “big” as their online presence can make them seem.

7) Benchmarking against competitors isn’t very useful

While there are non-trivial difference between us, BuySellAds.com is a legitimate competitor to isocket. We’ll talk about them on occasion and sometimes I really wish I knew how they operated. But ultimately, our success relies on our delighting customers – and doing it the best way WE know how.

8] Bipolar mood swings are normal

Working at a startup is often described as riding a roller coaster – there are extreme highs and lows – and I think the metaphor has held pretty true for me. It’s just something you gotta keep it in mind as you push forward.

9) People like to chat much more than email

We installed one of those chat widgets on the bottom right-hand corner of the isocket website and it’s been very insightful. We’ll get inquires, questions and feedback that we would never get in email. There’s something about the short, real-time-ness of chat that makes it really appealing – way easier than sending an email.

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10) In SaaS businesses, retention is huge

When you’re in sales, your incentives are often aligned to just close as many people as possible – to generate more revenue. With a business like isocket that charges a monthly fee, you make the money on the backend. You’ve got to bring people on with the right expectations or else they’ll quit soon after joining. Measure those customer retention metrics.

11) Taking breaks with coworkers is important

While the startup mentality is often “go-go-go” it can be really tempting to just hole up in the office all day long and just crank. While those days are critical for getting things done, I’ve found that a lot of our “a-ha” moments and bonding experiences have occurred when the team is out together for lunch or something. Don’t miss out on these just because you’ve got a lot to do.

12) Whiteboarding ideas is invaluable

At almost every startup office I’ve been to, I see multiple whiteboards on the wall that are covered with diagrams and phrases. I’ve sat in “whiteboarding sessions” and have seen first hand the power that whiteboards have in transferring ideas, building up systems and organizing projects. Powerful stuff.

13) You can’t let uncertainty paralyze you

Startups have soo much uncertainty involved – how soon can we get more kick-ass people on board, what new BD deals are coming in, what will Google do, how our existing customers will react to a major product update, etc. You have to recognize that while these concerns and unknowns are real – they must not stop you from gathering as much info as possible and making educated guesses.

14) Give people context

One thing that’s helped me a lot when doing sales calls is to give people context. When someone asks “How much does this cost” you might be tempted to just blurt the price and that’s it. Instead what you should do is show them why the problem the person has is quite severe and costly, how elegantly your product solves this problem, and how reasonable and fair the pricing is. People make better decisions when the information is nicely packaged together.

15) Estimating build times is hard

The ability to solve a problem and the ability to estimate how long it will take to solve a problem are two related but separate skills. Both are hard, but it’s often assumed that if you’re good at one, you’re good at the other and this is not the case. The sooner you recognize and adapt to it, the better.

16) Everything you do at a startup is hard

When you really think about it – everything about a startup is hard. You’ve got less resources to work with, less of a brand, less features in your product, less sure of who exactly your customers are. If you go into work at a startup and think everything’s fine and not too tricky to work out – you’re doing something wrong.

17) Big companies take forever to get anything done

If you think your startup hasn’t done a lot lately, take a look at bigger companies. Long release cycles. Projects that go nowhere. I’ve seen and heard of startups collaborating with bigger firms (which will go nameless) that drag their feet, bring in tons of VPs and ultimately are not worth the time. If you’re going to work with a big guy, be prepared.

18) Startup folks are intellectually curious

One thing that I loved about going to Stanford is that you could discuss a wide variety of topics within a group and everyone could add something valuable to the discussion. I’ve been pleased to notice that in the startup community (unlike many other places) that same broad/deep range of knowledge, willingness to explore ideas, and desire for substantial conversations continues.

19) Using virtual assistants is like “programing with humans”

We’ve been using virtual assistants (VA’s) to automate certain processes and while on one hand – it’s pretty amazing how much stuff you can get done for not a lot of money, they can also be quite challenging to work with. Like programming a computer, you have to give the VA’s good instructions and you often have to course-correct (fix bugs) your instructions multiple times along the way.

20) Rarely is a startup doing as well as the team says

The data indicates that majority of startups go under. So when you hear people say that things are “going really well” at their startup, you always have to take it with a grain of salt. If you work at a startup, don’t get discouraged by hearing of the success of others – they probably exaggerating their successes to some degree and likely having numerous difficulties – just like you.

21) Be ready to bail on other commitments at times

There have been times where I’m hanging out late at a bar with friends when a major customer issue comes up and I have excuse myself, get home, sober up and take care of it. Your friends and family need to know that while you want to make the most of your time with them, there are times when, like a doctor in the ER, you are summoned. And you’ve got to take it.

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22) Don’t forget to stop working once in a while and have fun

Given that you’re already working hard and potentially sporadic hours – it’s doubly important to find some time to rest/relax/play. Continuous 70 hour work weeks are not compatible with creativity and mental agility – which are just as important as output for a startup.

So there you have it 21 + 1 lessons learned after 21 weeks at a startup. Did I miss anything? Did I get it wrong? Leave a note in the comments!

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Jason Shen

Jason is a tech entrepreneur and talent expert. He is CEO of a performance hiring platform called Headlight, a Fast Company contributor, and an advocate for Asian American men. Follow him on Twitter at @jasonshen and subscribe to his private newsletter.

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  1. Jason – I’m very impressed and proud of how much you’ve stepped up and aggressively embraced the start-up culture, challenges, and fun. If you keep your eyes and mind open as you’re clearly doing, you’re going to do fantastic things. I’m looking forward to watching.

  2. Whoa. This is a really good post. I’m bookmarking and sharing this in my FB group.

    We went to HD to make giant wall size whiteboards. I think it ends up being around $50 bucks, but super invaluable

    Me – http://tech.rawsignal.com

  3. Thanks Troy. Mega whiteboards sounds awesome! I know a friend who has his dorm room covered in the stuff – very handy.

  4. I really liked this post. Came across it on Twitter and will be sure to share it. Unlike many lists, this was great and perfect for me to reflect on with the position some companies I work for are in right now.

    Definitely checking previous posts.

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  6. Jason,

    Awesome blog post. Great to hear you’re loving things at iSocket. I’m sure you guys are killing it right? (insight #20)? Truly an awesome example of 21 (22 i guess actually!) key insights on what being at a start-up is like. Will share this with all the budding entreprneurs from Ohio State that are part of our Business Builders Club.

    An email will be on the way shortly…..terribly derilect (sp?) on my part.


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  9. Awesome post, thanks for the tips. 6 months into my own startup, these tidbits of advice are a handy reminder of how to stay focused and reinforce that I’m on the right track.

    Congrats on the acq!


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  16. AT the beginning of the journey, and I cannot help but agree with all of the points you said. Especially no 22. If you lose the fun in a startup, I hardly doubt it can survive the 10% of statistics of startups which survive

  17. Just recently switched to a startup and A lot of these ring true, especially the side project comment . As to the whiteboarding, at our ship we use IdeaPaint on at least one wall in every room. It turns the entire wall into a whiteboard.

  18. Hey Jason, thank you VERY much for this post. I am a community management intern at livefyre , which is how I was fortunate enough to stumble across this post! As someone who is not only new to Livefyre, but also new to the startup culture entirely, I benefited from this post on many different levels.

    Thank you so much for taking the time to share your experience at iSocket. I hope you don’t underestimate the value this post can hold to someone in my position. I am excited to browse your through blog and the links in this post, and will surely be leaving more comments soon!

    • @JonHearty livefyre Thanks Jon! I’m glad you’re getting a lot out of this post. I’m sure in a few months you’ll have your own awesome list of lessons – and I want you to send it to me!

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  21. Lessons worth reading. Most frequently lessons learned helps for the smooth and systematic operations of the startup and apparently gives a platform for the same. But I wonder how much dedication is required for the set up a startup. This is quite an informational post. I feel myself lucky to come across this wonderful post learning a good set of approach to figure out the significance. Thanks for sharing the same.

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