SendGrid Startup of the Week 13: Jacqui Boland of RedTricycle





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This episode of TWiST is a special Startup of the Week Show, with Jacqui Boland of RedTricycle. RedTricycle offer ideas for cool things to see, eat, make and do with your kids in your neighborhood.

0:00 Today on the program we have Red Tricycle, the site that tells you what to do with you kids every weekend
1:30 Go to
2:10 Thanks to SendGrid
3:30 Let’s get to Red Tricycle
4:15 Jacqui Boland founder of Red Tricycle, how are you?
4:45 Tell me the metrics from the last couple of years.
5:50 What was it that lead you to believe that this could turn from a hobby to a real business?
7:50 So it was outside factors really that drove you to make the leap?
8:05 Is there a message in that that comments on big businesses ability to stay focused?
9:00 Wid you think you had to get off of email and get onto Facebook?
11:00 Talk about simplicity and product development.
12:15 Do you think your customers would prefer an app experience to an email?
13:30 Would people pay for this service?
15:00 How did such a small site bring in such big national sponsors?
16:00 What do they call the type of advertising you are doing on the site?
16:30 How do you balance the big advertisers with the intimae user experience?
18:20 How would you decide as the founder to accept/not accept a controversial advertiser?
19:40 Have you ever offered a premium product? Do you think it’s better to go for the ad buy?
20:40 Are Angels or VCs interested in content based sites like this one?
23:15 What are the challenges of scaling up?
25:00 How do you maintain editorial excellence?
25:50 What is something that you wouldn’t include as a Red Tricycle event?
27:15 Did you ever consider the Groupon model?
28:45 Have you thought about an event-booking engine?


Jason: @jason
Jacqui: @redtricyclemom
Red Tricycle: @red_tricycle

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