Despite not raising significant funds, we decided to launch Twilio on November 20, 2008, and immediately started gaining customers who were willing to pay for our service.

I pitched 75 investors for funding, but we faced rejection after rejection, which made me cynical about fundraising, especially during a time when no one was investing in consumer-driven businesses.

Despite the difficulties in raising funds during the economic collapse of 2008, we managed to secure our first investment through a college business plan competition.

Raising our first half a million dollars was more challenging than raising our first $200 million, as investors were skeptical about mobile voice technology at the time.

In 2008, during the financial crisis, many biotech companies were going out of business, which made it a challenging time to raise money.

I didn't sell my story well to investors, which led to challenges in raising funds, but eventually, we built a strong case that made it hard for them to ignore us.

After struggling for a year to get the Airbnb marketplace going, we decided to apply to Y Combinator in the fall of 2008 as a last-ditch effort.

I faced significant challenges in fundraising, as I had no connections in Silicon Valley and struggled to secure initial funding for Watsi. No one wants to be the first person to take a gamble and support you.

When I pitched the idea of building a Bloomberg for startup investors, it sounded ridiculous, but the investors ended up investing on the spot.