SendGrid Startup of the Week 12: Oleg Kostour of Pair



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This episode of TWiST is a special Startup of the Week Show, with Oleg Koustour of Pair. Pair gives couples a way to combine all of their communication into one outlet. Jason and Oleg talk shop delving into the history of Pair, app security, and the Startup Scene in Canada.

0:00 Oleg Kostour of Tenth Bit Inc. is on today
1:00 SendGrid Try the free plan send up to 200 emails per day for free
3:20 What is Pair? Why did you build it?
4:20 What was the original idea? What did you pivot from?
5:05 So you sold the crew on a CAD product and then you had to pivot? How did you sell that?
6:15 Tell us about the application process yo YCombinator?
7:30 Tell us a little bit more about the product.
9:00 Who is first inviting their spouses do you find that it’s men or women?
9:45 Who’s more active after they Pair, women, men, gay, straight?
10:30 Where did the inspiration from this ap come from?
11:45 Do you think sometimes great entrepreneurs just take a product to the next step?
12:15 What happens when a couple breaks up?
13:45 So you are trying to get more information from your users, before you solve all the problems?
14:40 Have you sexted with Pair?
15:10 How does sexting complicate your business?
16:00 Is it encrypted so your staff could get to the content?
16:20 Realistically how hard would it be for a disgruntled employee to hack your system?
17:40 How does Facebook’s privacy policy affect Pair?
20:30 Oleg how old are you?
23:15 So you have a very long runway currently? What are your thoughts on monetization?
24:15 So you have had troubling with immigration into the US from Canada?
25:00 How are we 4 years into the relationship with Obama and still having trouble getting founders into the US?
27:15 Tyler’s thoughts on Obama’s immigration policy
29:15 Are there to many companies graduating out of YCombinator?
33:00 Thanks Oleg
33:45 Can I have more than one relationships with Pair?
35:15 Go To


Jason: @jason
Oleg: @olegkostour
SendGrid: @sendgrid

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