A two-time entrepreneur shares the timeless lessons she took from her first venture to apply at her second startup.

By Monika Kochhar (CEO & Founder, Smartgift)

The reverse of what not to do is what actually worked. In our last business, while their were inevitably a few weeds, we also managed to grow a verdant garden bearing many fruits. There were things we figured out by trial and error that proved instrumental to our success. As I build out Smartgift (entrepreneurship is a terminal bug of course) with my co-founder and team, we often go back to our little black book of what worked previously. Here are the top three rules that we take to heart and would not budge from.

No One Can Sail Alone

Find yourself a dependable partner. If you can’t convince anyone else to jump on board and navigate the waters with you – think again. Startups by their intrinsic nature are volatile. It’s priceless to have another person riding out the storms with you, slaving until the rooster crows and being as vested in the success of the business as you are.

Part-timing or moonlighting will not get you anywhere. In the sink or swim world of startups, wearing a life vest keeps you alive but gets you nowhere. Both founders should have skin in the game and be fully committed. At least one of the founders to take the plunge full-time. Building a thriving business is a marriage of innovative ideas and meticulous execution. It’s also a marriage of the people involved. Make sure you choose the right partner to make the marriage work.

Build an In-House Team

As tempting as it might be to outsource, especially when bootstrapping, it’s an inefficient thing to do. In a startup, things move fast and feedback cycles happen quickly. There is little time for long wireframes, briefs, minutes of meetings and more meetings. It’s an action intensive environment that needs quick results. When the team is built from within, each member is focused on your product only and shares the same motivation – to drive maximum value for your business.

Don’t Be Scared to Start Over

It’s scary to wipe off the blackboard and begin again. But if the build, measure, learn cycle and key metrics point only to red – it’s time to stop and analyze how to move forward. A pivot can be a deeply cathartic experience. Keep development cycles short and user experience test every single detail of the business. In fact, we really did have our grandmother test out Smartgift and she loved it!

Serial entrepreneurs: What are the top lessons you took away from your first startup?


About the guest blogger: Monika is the founder of Smartgift, a provider of online gifting technology for retailers. Before founding Smartgift, Monika was a business development and strategy adviser to Guguchu, a platform used by musicians, managers and music labels to better connect with fans. It was acquired in 2012 by The Orchard.