Outtakes from the first Social Sharing Angels Lunch

Bringing together angels & 4 startups trying to revolutionize next-generation travel

We didn’t know quite what to expect when we came up with the idea, two months ago, to hold the first Social Sharing Angels Lunch. But we did know that the current way of connecting promising startups with angel investors is pretty lame.

So it was a bit of a surprise that the unanimous verdict from participants was that yesterday’s event was, in the words of George Arabian of Steelhead Ventures, “a superb idea that’s so much better than the usual speed dating events” that fill the calendars of venture capitalists, angel investors and startup founders.

I haven’t written a lot about Cruiseable’s fund-raising efforts, given that readers are chiefly interested in our product, tools and services rather than our business model, but it’s worth a blog post to capture the positive energy that resulted from yesterday’s meetup, in case others want to replicate it.

Origins of the Social Sharing Angels Lunch

First, about the format. Like the thousands of other tech startups in the San Francisco Bay Area, Cruiseable faces the daunting challenge of attracting angel investors’ interest. I don’t care what anyone tells you: If you don’t personally know a large number of angel investors, it’svery hard to get their attention unless your startup is already getting lots of traction (growth, revenue) or have some big names behind you. Which is why thousands of startups flock to pitch sessions (Startup Grind, Founders Space) or join accelerators or apply to big events like the Launch Festival and TechCrunch Disrupt.

The trouble is, these events often ultimately reward showmanship over more important factors — your product, your team, the size of the market opportunity, your business model, your go-to-market strategy — and offer a poor setting for genuine give and take. I will bet you that many of the best startups are the ones that apply but don’t make the main stage, and the ones that bypass speed dating altogether.

Thus, the idea for a Social Sharing Angels Lunch.

BlogHer co-founder Jory Des Jardins, one of Cruiseable’s advisors, connected me with Ilana Golan, founder of Stiya, and we connected at the Launch Festival in March. We did some research and found two other startups with similar potential for revolutionizing the travel sector.

Next, I approached a social dining startup, Feastly, with the idea of holding a lunch in a chef’s home, rather than a noisy restaurant. We settled on a small venue in the Dogpatch neighborhood of San Francisco, The Lab, and selected a chef, Lindsay Kinder of Food La La, who prepared a green salad, a main dish of Seafood Orzo (fresh orzo tossed in a lemon and garden herb dressing, studded with feta cheese, roasted shrimp, and mini scallops) and finished with Sweet Bites, including chocolate-covered strawberries and delicate French macarons for $45 per guest (the startups split the bill).

Next, we created an Eventbrite invitation for the occasion and also spread the word on Twitterand LinkedIn and by creating a Facebook event. (I didn’t know that I’d have to spend a lot of time uninviting founders of more than 30 startups that loved the idea and wanted to apply to do a mini pitch. We may decide to hold another one.)

But the hardest part, of course, was getting angels’ attention. It took dozens of hours to identify Bay Area angels that have funded travel tech or mobile startups, through tools likeLittle Bird and platforms like AngelList. (We asked for help spreading the word from some heavy hitters in the space — and received none. Just one more barrier to overcome!)

The participating startups and founders were:

• Cruiseable: a personalized one-stop shop to find, plan & book a cruise vacation that’s perfect for you. Founders JD Lasica (me) and Giacomo Balli. Guest: John Bell of the Travel Leaders, Advisor.
• Stiya: a tool that captures experiences and creates automatic journals including location, photos, map and notes, allowing you to share your complete story on any social media. Founder Ilana Golan.
• Goconnekt, which allows travelers to connect their mobile devices from anywhere without roaming charges. Founder Merwan Benhabib.
• Outdover, a new mobile app that helps outdoor enthusiasts plan nearby outdoor activities in seconds. Founder Roberto Bustillos.

Participating angels and VCs (whose names we’ll chronicle here for the sake of posterity) were Craig Kent of Seed Round Ventures, Reese Jones ofSingularity University, Paolo Privitera of Start-Up Chile and 500 Startups, Audrey Melnik of Funnel Ventures, George Arabian ofSteelhead Ventures andAdrienne Huesca, an advisor for Pipeline Capital Partners — though please don’t take this post as a sign that they’re open to pitches without a proper introduction.

While I can’t give you a blow by blow of the conversation — we didn’t ask permission to use attendees’ quotes — I can tell you that the give and take was “much more than I expected,” as Ilana put it. The discussion, with a few hard-edged questions here and there, centered on business models, recurring revenue, go-to-market strategies, cost of customer acquisition, offloading costs through B2B2C business partnerships and the challenge of getting your app seen and used in a universe of 3 million competing apps.

Food for thought.