“It’s my life goal to be 300.” — Eschewing work life balance and staying relevant.

This is Aksh Gupta, Cofounder of Technology Startup Occasion and the man who taught me everything I know about working lean and introduced me to the Chicago Startup scene.

While the entire Occasion team was greatly influential in teaching me about business building, Aksh in particular introduced me to the importance of focus. Through words and actions, he taught me to focus on one thing you believe in and put 150% of your effort into it. If you let yourself get swept away with ADD entrepreneurial tendencies, you’ll lose your ability to be effective. We sat down last week at 1871, A Chicago Coworking Space, to catch up.

RILEY MASUNAGA: What is the elevator pitch for Occasion?

AKSH GUPTA: Occasion is online booking and payment software for businesses. It’s easy to use and easy to deploy and it’s a great experience for the customers.

We launched our product in September, and since then we’ve grown from about 12 customers to 38 now. In terms of key metrics, booking volume [client order volume] and number of bookings are both 50% higher now compared to January, and our revenue is growing at about 30% a month.

RM: What is your biggest struggle going forward?

AG: I don’t know… There are too many battles we fight. Coherent marketing, lead generation, product feature road map, from an operational standpoint, automating tasks and making sure merchants are successful when they use our product.

We’re spending a lot of time learning what makes a merchant successful the minute they sign up so that we understand why it makes sense for them to keep using our product.

RM: What is a piece of advice you wish you had known before starting Occasion?

AG: Advice… God this is a tough one. There’s a lot of things I wish I had known. I guess, it always takes longer than you had planned. Anything — number of sales, customers, marketing, it always takes more time than you had originally planned.

The other [piece of advice] is to learn time management. There’s a lot of work immediately to be done, and it will only grow with time.

RM: What is your work life balance?

AG: I don’t get the concept of work life balance period. If you’re working for yourself, there are very few moments you can stay disconnected… Not to say you should be working all the time — staying connected is different from working all the time.

RM: What’s the best advice you’ve ever received?

AG: Stay relevant. That’s general feedback I promised myself everyday to stay relevant in terms of technologies out there, what’s going on in the world. The pace of change is so fast. Whether you’re an entrepreneur or student the pace of change is so fast.

RM: Do you remember who told you that?

AG: I invented it. I was talking UIC College of Business’s incoming class, and the person moderating the panel was like, ‘What’s your advice for these students?’ and at that moment this all that I could think of… Afterwards, I thought about it and said, ‘Actually that’s pretty good. That’s what I’ve been doing’

RM: What do you remind yourself to do everyday?

AG: There’s a lot of different things. Now that I have a team of people, I want to be a better ‘manager’ for them. I need to be effective at communicating, motivating and challenging. You can come off as very disrespectful if you do any of those three things the wrong way.

RM: Who is your hero or person you look at aspirationally?

AG: I get asked this a lot, and I don’t have a hero or superhero. I’ve always been very good at learning positive things from observation by talking to people. For example… One of my mentors is super responsive — you send him an email and he responds right away. I’ve seen people open doors for me. I’ve seen hardworking people with families who check into the offices at 7:45 and leave at 6 PM.

I don’t have a super hero, I’ve learned many different skills from many different people.

Anything else?

Hmm… It’s my life goal to be 300.

That’s a lofty ass goal. You better hope Google comes forward with their eternal life thing. That’s not something you can hard-work together so good luck with that Aksh.

[laughs] Thank you — I’ll need a lot of help to get there. It’s a very philosophical thing. If you look at my grandfather’s lifespan, he was born in 1931 and died in 2005. The amount of change and tech innovation that occurred in 80 years is just 80 years in just amazing. You can only imagine what the next 80 will look like right now!

Now if you extend 80 years to 300… Wouldn’t you want that super power?