When Olark passed the 10K customer mark in 2015, my co-founders and I reflected on five years of bootstrapping and building Olark live chat from a hobby to a business. We have lots to be thankful for, but I am most thankful for my awesome and flexible teammates who care about how we work together.

The challenges we took on in 2014 raised tough questions about our organization. What are our most important projects? How do we determine our priorities? How do we find the right teammates to solve a problem? Who makes decisions in a "flat" structure? Should we remain flat?

Olark is the first software company I co-founded. Starting out I really had no idea what to expect. Previously I worked for several years as an early employee at another startup, so I had a fuzzy picture in my head of what I wanted Olark to look like, but I wasn’t sure how to get there or how long it would take.

Now it’s 2015, our team is over 30 people, and we have thousands of customers. People ask me all the time about those early years: how long it took to become profitable, what “typical” revenue growth looks like, or when to make that first hire. Time has really put those first few years into perspective, and as we get set to cross a major customer milestone next week, I thought it’d be helpful to share what those early years were like for us.

Conspire used Olark to answer questions during a 100x traffic spike, and continues to use live chat to keep its massive (and growing) database up-to-date.

CommitChange.com currently works with nonprofits looking to raise funds via crowd fundraising, event ticketing, or other means. Based on each non-profit's needs, CommitChange.com builds them a customized suite of tools to manage their campaign and achieve their fundraising goals, all from a single platform.

The company currently services more than 300 nonprofits across the United States, recently released its first monthly subscription tier for its core fundraising suite, and had more than 9,000 donors use the CommitChange.com platform for their charitable giving in 2014.

Nothing is more exciting to an entrepreneur than a new user, standing at the precipice, poised to convert. So much could go wrong at this moment. Will they put in their email address? Will they go to the next screen? Will they enter in payment information or share referrals? Is your product even right for this person?

When I became Olark's Chief Storyteller, I became interested in the idea of "Happiness Hacking": trying to optimize your product and UX to create loyalty and deepen your relationship

Today's guest post is from Angelica Valentine, Content Marketing Manager at Wiser. You can follow her on Twitter here: @AngelicaSaidSo.

Every retailer knows there are plenty of opportunities to maintain and even grow their sales after the holiday rush. January is a prime time to strengthen customer relationships and extend the life of those initial purchases or even inquiries that happened in late November and throughout December.

Retailers - before you pack up the tinsel and declare the holiday shopping season 'over,' it's a great time to stop and reflect on what worked and what didn't.

I was curious, so I asked some online retailers, "What lesson did you learn from this year's holiday shopping season? And what will you do differently in 2015 knowing what you know now?"

Check it out -- it's our 2014 Holiday video! 

Today's post comes from Diego Torres-Palma at HapYak. HapYak has developed a technique for adding the Olark chat box to videos, so you can chat with customers inside of any video: