SendGrid Startup of the Week #5 - Nate Stewart of ZingCheckout

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On SendGrid Startup of the Week #5, ZingCheckout co-founder Nate Stewart joined us from Austin to explain how his POS system is giving Square a run for its money.

0:38: Welcome to Startup of the Week! SendGrid ad

3:25: What is ZingCheckout?

4:15: How is this different from Square?

5:25: Why did Square go native app? Snobbery of Silicon Valley elite or strategic decision to drive iPad sales and have better user experience?

6:38: Are you aiming at mid-size companies, large companies?

7:35: What's it like going up against Square, now a multi-billion-dollar company? What is that like as an entrepreneur? Too herculean to convince investors, get employees?

9:15: What about the price difference? How does this compare on price basis to something like Square or traditional POS?

9:45: What do they charge per month, a traditional POS?

10:20: When you try to get larger location to adopt, how do they react to $49 price?

11:25: How important is reporting in all of this? How hard is it do reporting in traditional POS?

12:30: You are in Austin now, started in Los Angeles -- further and further away from the Valley. What is the thinking there?

14:30: 176 followers on AngelList and a lot of positive comments. Nolan Bushnell as advisor. How has AngelList process been for you guys?

15:40: You have Nolan and [ Nimble founder ] Jon Ferrara as advisors. Jason notes he invested in Nimble. How does a 29-year-old, first-time entrepreneur land such advisors? [ Nate says Ferrara is only a reference; he saw product at SXSW ]

17:15: How do you land a high-end advisor, how does it work?

19:15: What's next? Panic out there with Facebook and Zynga crashing, brutally depressing to be raising an angel round? What is your sense of the angel market today?

20:20: Seems like your team is all engineering or product. Is the fourth person product or sales?

21:30: I think that gives you a leg up, that you are a product-driven team. To build a Square competitor for $50k that works -- I take it people are impressed?

22:45: What is the big struggle right now: raising money, getting customers? What keeps you up at night?

23:50: You could be the front-end for somebody else? A merchant bank?

24:15: You call them ISOs?

25:15: How do you decide on how much free to give in your freemium model?

27:15: Would you take $1k from 1k people?

27:30: What if it were 100 people at $10K each?

28:00: Thank you, SendGrid! See you next time.

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Jason: @jason
Nate: @becomevocal
ZingCheckout: @zingcheckout
SendGrid: @sendgrid