Startup Stories – Lessons Learned This Week

Last week after I posted about what I learned raising our Series A round, I got a lot of positive feedback. And a few folks suggested that I should post a regular ‘lessons learned’ series, especially as we grow in our early startup stages. Great idea, and something I wish I woulda started a year or so ago when Dasheroo was just hatched.

Anyhoo, these won’t be too lengthy. Doesn’t mean I don’t learn something daily, but I’m gonna keep it brief anyway (is it OK to use ‘anyhoo’ and ‘anyway’ to start and end two consecutive sentences?) Also we’re not going to be too literal about ‘lessons’, it may not be a lesson,  just a ‘thing’.

Here we go, some interesting things from this past week:

  • Glengarry Glen Ross

    Image courtesy Glengarry Glen Ross

    ABD (Always be demoing): It would be so easy for me to say “hey, it’s simple. Just go in, connect an app or two and voila! you’ll have a dashboard in 5 minutes. You don’t really need a demo, do ya?”  Well, demos allow you to connect with people, give them your vision and most importantly, get live feedback! Plus it keeps you fresh & on your toes, and who knows you might get a great review. Thanks Small Business Computing and SaaScribe!

  • Keep in mind the importance of enterprise-level selling early on: We’re very focused on getting Stripe, our billing solution, in place and we announced three pricing editions. These are all under $100/month (our entry level ‘Tall’ edition is free, and until June 15, 2015 our ‘Grande’ version is free too!) and we plan on converting and upgrading users at these pricing editions through the app, no salespeople needed. That’s awesome, but read here for a very insightful article about the importance of establishing enterprise-level sales early on if you truly want to become a huge, global and valuable business. One tidbit: “…SaaS businesses that focus their cultures and organizations solely on this model will eventually face significant challenges when trying to scale beyond initial adopters to build and grow from a larger base of revenue.”
  • Don’t just QA your app, QA your www too: We got a few slams this weekend about the mobile experience on our website (poor or no scrolling) after the awesome folks at Y-C Hacker News mentioned us. Hey thanks on 2 counts – we had one of our best signup days so far, and it highlighted a poor user experience that we jumped on immediately.
  • All I know is, if I was applying for a job at Dasheroo (or anywhere for that matter), I’d make sure to get an account and poke around the product before my interview. I was reminded of this, this past week as I was conducting initial interviews for a couple positions here. Almost no one had bothered to create an account! Seriously? And you think you can talk about selling or marketing it?!
  • My new pal, Ted Rubin, who owns the phrase “Return on Relationship” loves bleu cheese stuffed olives in his martini. Gotta love that!

So what do you think? Lemme know if it’s B.S. or onto something good, and what could be improved, OK?

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