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Best of Bootstrapping: Bootstrapped to $10M First, Raised $25M Later

Posted on Monday, Aug 7th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  “Bootstrap First, Raise Money Later,” is the 1Mby1M mantra. Ashik Ahmed, Co-founder of Deputy, shared his story in 2017 of bootstrapping to $10 Million from Australia before raising $25 Million from the US in the first external financing. Sramana Mitra: Where are you from? Where were

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Best of Bootstrapping: Bootstrapping to $10M from Australia, Raising $25M from the US

Posted on Tuesday, Jan 4th

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.  “Bootstrap First, Raise Money Later,” is the 1Mby1M mantra. Ashik Ahmed, CEO / CTO Co-founder of Deputy, shared his story in 2017 of bootstrapping to $10 Million before raising $25 Million in the first external financing. Sramana Mitra: Where are you from? Where were you born,

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Bootstrap First to $10 Million from Australia, Raise $25 Million Later from the US: Ashik Ahmed, CEO of Deputy (Part 7)

Posted on Sunday, Apr 23rd

Sramana Mitra: Where did you choose to raise your $25 million financing from? In Australia? Ashik Ahmed: Funny story was that every morning, we’d wake up and there’d be an email from some VC. I wanted to focus on growing the business as opposed to getting interested in VCs. In mid-2006, we realized that our

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Bootstrap First to $10 Million from Australia, Raise $25 Million Later from the US: Ashik Ahmed, CEO of Deputy (Part 6)

Posted on Saturday, Apr 22nd

Sramana Mitra: When did you start the Gusto partnership? Ashik Ahmed: That was between late 2013 and early 2014. Sramana Mitra: How much did you do in 2014? How would you attribute that to Xero, Gusto, and your direct selling efforts? Ashik Ahmed: The challenge with partnerships is that, at the start, you get a

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Bootstrap First to $10 Million from Australia, Raise $25 Million Later from the US: Ashik Ahmed, CEO of Deputy (Part 5)

Posted on Friday, Apr 21st

Sramana Mitra: From a customer acquisition point of view, how did you go to market? Ashik Ahmed: It was really, really hard. We spoke to a lot of customers. In the second round where we went for anyone can just sign up, you don’t need to get the word out. Back then, I don’t think

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Bootstrap First to $10 Million from Australia, Raise $25 Million Later from the US: Ashik Ahmed, CEO of Deputy (Part 4)

Posted on Thursday, Apr 20th

Sramana Mitra: Did you fire the CEO that you brought on? Ashik Ahmed: Yes. Sramana Mitra: How did that go? Ashik Ahmed: Not pretty. I doubted myself whether I would be capable of being the CEO of this company. I didn’t even know what the job description of a CEO looked like back then. My

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Bootstrap First to $10 Million from Australia, Raise $25 Million Later from the US: Ashik Ahmed, CEO of Deputy (Part 3)

Posted on Wednesday, Apr 19th

Sramana Mitra: From a vertical point of view, it was all in the hospitality area? Ashik Ahmed: That’s correct – all restaurants, bars, and hotels. That was the industry we were focusing on. Sramana Mitra: How many customers are we talking? Ashik Ahmed: By the end of 2013, I believe we only had 150. Sramana

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Bootstrap First to $10 Million from Australia, Raise $25 Million Later from the US: Ashik Ahmed, CEO of Deputy (Part 2)

Posted on Tuesday, Apr 18th

Sramana Mitra: This is an Entrepreneur Journeys story. I’m going to help you tell that story as a journey. You started with this concept back in 2008 with your co-founder. What was the first thing that you did? Ashik Ahmed: Coming up with the name. To be honest, I resigned from Aero-Care in February 2007 because I

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