Milind Mehere is a repeat founder who has created, funded, and sold companies to the tune of hundreds of millions of dollars. His latest startup is honed in on ‘self-driving money’ to help others improve their own finances while freeing up more time.
During our interview on the DealMakers Podcast, Mehere shared his adventure so far. We talked about everything from how to get started as an entrepreneur to hitching hiking through the desert to investor meetings in other countries, managing through a crisis, and what makes it easier to raise money for your second startup.
The Engineering Mindset
Milind Mehere has ridden the rollercoaster of building and scaling several successful companies. This journey all seems to stem from his childhood and affinity for engineering.
He was born and raised in Mumbai, in a period of great growth, innovation, and optimism.
The government had recently opened up the economy. People were inspired to develop new technology and saw many new possibilities.
Even though he comes from a family of entrepreneurs, as with most children in India there was a lot of focus on education. There was still that pressure and expectation that you should either become an engineer or a doctor.
Biology didn’t seem to be his thing, but he loved tinkering with things and math. So, he pursued mechanical engineering. Then he went on to study industrial engineering, and his grad school took him to the United States.
He says that engineering training and mindset definitely helped prepare him for entrepreneurship. It helps to break down and solve problems, and professionally measure, analyze and find ways to improve and be more efficient.
How To Manage A Crisis
After grad school, Mehere landed his first job with i2 Technologies and got to experience the full cycle of a company.
It was a software company helping retailers with logistics. He joined when the company was just a few hundred people. Still, in his 20s he was managing a group of 50 to 80 others. By the time he left they had several thousand employees and were worth $60B.
The company scaled fast in the dot com boom. Then he got to experience the stress of the bust and what that meant for managing a company in other phases of the market too.
He learned the importance of understanding the size of the crisis when formulating your response. Entrepreneurs are working in the middle of chaos every day. Even on the good days.
So, understanding whether this is just another day, or it is a 2008 recession, or a pandemic level crisis like COVID is important to differentiate.
Clinging to your true north is also vital in these times. He says he has witnessed many entrepreneurs hurt themselves by flip-flopping too much. Constantly chasing new ideas and changing things, and leaving their teams in a daze, without direction.
His other tips for managing through a crisis include:
- To know our strengths as a company
- To be a fast decision-maker
- To take the problems head-on
- Create a plan
- Motivate and rely on your team
The $342 Million Exit
After i2, Milind joined an MIT startup, which had gone through one of their first startup competitions. Old Systems was funded, innovating, and tackling RFID, which was the basis of big data and IoT, well before those terms were so popular.
Then he agreed to listen to a pitch from another entrepreneur if he would pay for the drinks that night. This turned into a new founding team that created Yodle. An early online advertising company that was helping small businesses.
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