The insider story of Dropmysite on Angels Gate

Angelsgate lift

A little over a year ago, I was a contestant on Angels Gate, angel investor reality show. I came, I pitched and I was funded. On camera, it may seem like it was a piece of cake but the ride was an arduous one. I believe I became stronger after that experience and I would like to share that adventure in detail.

1. Pre-Screening

At the time of receiving the application to be part of the show, I was still working on my 1st tech startup, EatAds – the online marketplace to buy/sell outdoor advertising. I entered on the basis of that business and was quite confident of its success on-air and off-air.

2. First Elevator Pitch (Up)

A while later, I was called in to start the first round of filming. By then, I was already on a new venture, Dropmysite. The EatAds website crashed due to a hosting failure and I lost a bunch of data. It was embarrassing to apologize to clients for someone else’s mistake – many of whom never returned. As there wasn’t a suitable remedy in the market, the inspiration struck to build a product to back up websites. This was before pivoting to Dropmyemail, the most comprehensive email backup solution in the cloud.

I got mic-ed up and I walked into the lift with one of the angels, William Klippgen (Singapore-based Norwegian entrepreneur and technology investor). I had 30 seconds, while the elevator went up, to pitch and if what I said piqued his interest, I get to do a full pitch to all the Angels. As I was talking about backing up websites, Klippgen looked confused and rather upset. He was under the impression that I would be talking about outdoor advertising so he turned me down.

I walked out of the lift feeling dazed. I was not expecting to be tossed out without getting to layout my business properly. It was a horrifying feeling.

3. Second Elevator Pitch (Down)

Following which, there was a short discussion between the producers, Klippgen and me to clarify what was going on. I talked about Dropmysite’s traction – 8,000 signups in 3 months and tying up potential reseller deals with Reliance Telecom in India. Klippgen heard this and said, “Let’s do it again.”

Though glad to be called back in for a second chance to pitch, I was still nervous as I botched it once before. This time as the lift ascended, I stammered slightly while delivering my speech. On the top floor, Klippgen gives it a moment’s thought and says ok. I’m relieved to be finally making it to the Angels Gate.

4. Between the Elevator Pitch and The Shoot

Following this, there was a two-week wait. I constructed the best deck of slides I could and yet I wasn’t 100% sure. I handed it to a trusted friend, Nicholas Gan, to look it through. After numerous tweaks, the slides looked better.

At this point, Dropmysite’s traction improved to 15,000 signups. While that is great, my bootstrapping funds are running out and I’m having issues paying rent that month. So for me, this pitch is a last toss of the dice for my family’s future.

5. 1 hour before The Shoot

One of the Angels, Ken Mandel, came up to me and asked what I will be pitching. He was surprised that I was going to talking about Dropmysite instead of EatAds. He told me someone was just tossed off the show for pitching something different from their initial application. To be rejected based on a technicality would be a nightmare. Hurriedly, I got a new application form and changed out the details.

6. The Shoot

It was time to pitch like I’ve never done before. You can see my vintage slide deck here.

Despite still slipping up slightly, I did the best I could and my gut instinct told me that the show would want to negotiate any deal I offered so I made a decision to increase my demands to 20% stake for $350,000 at a $1,750,000 valuation from original demand of 25% for $200,000.

Then, it was time for the Angels to discuss and for me to sit on the edge of my seat in the green room. Though the segment aired was around 15 minutes long, the actual filming took around 10 hours to complete. An eternity passed and I was called back into the studio. The Angels said yes to invest and my heart leapt.

In truth, I understood that as a reality show, the negotiations would be part of the entertainment. So in fact, the offered package was my reserved price for parting with the stake. I earnestly agreed to the deal.

7. The Aftermath

After the spotlights have dimmed, it was back to reality. The fund behind the show expressed interest in both EatAds and Dropmysite so we went through a few round of discussion. The final amount I got for both businesses was in fact $365,000.

I was elated that both my businesses are now funded well enough to grow fast and lean. It was a huge relief that I can continue to put food on the table. In my entrepreneurial escapades, I’ve suffered many setbacks and kept coming back for more. The main takeaway from this roller coaster ride is – never give up. Sticking to your beliefs till the bitter end might actually be quite sweet.

Now that you know the inside story, see the video of the full episode here and the insider interview here.

Angelsgate judges

The judges from the show