E1015: Open Office Hours LIVE! Jason helps founders with their biggest challenges: gaining interest from investors, scaling while bootstrapping in a niche market, automating operations tasks, acquiring national customers & focusing on customers in the cannabis compliance space @ WSGR

This Week in Startups

Jason Calacanis

Technology

4.4 • 1.3K Ratings

🗓️ 3 January 2020

⏱️ 67 minutes

🔗️ Recording | iTunes | RSS

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Summary

0:47 Jason intros Open Office Hours
2:15 Trevor from Moovin (on-demand software to rent professional furniture) asks Jason to share some hacks on how to gain interest from investors
18:31 Jelica from Saddle Shoppe (e-commerce luxury equestrian clothing/gear) asks Jason best practices on scaling while bootstrapping in a niche market
34:49 Antonio from Youcanevent (event services marketplace) asks Jason what and how to automate operations tasks
44:44 Ossie from PICKL (B2B product/consumer data platform) asks Jason about acquiring national customers outside of California
55:57 Jontae from NatureTrak (compliance platform connecting Cannabis companies and banks) asks Jason about staying focused on different customers in a two-sided marketplace

Transcript

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0:00.0	This Week in Start-Up's is brought to you by Zappier, the easiest way to automate your work.
0:07.0	It connects all your business software and handles the work for you so you can focus on what matters most. Right now through February try Zappier
0:16.0	free for 14 days by going to zapier.com slash twist.
0:21.0	Masterworks.io The first company allowing investors exposure into the
0:25.9	blue chip artwork asset class. Skip the 5,000 plus person wait list by going
0:31.8	to I. Masterworks dot i.o slash twist and health
0:37.2	IQ take as little as 20 minutes to save up to 41% on life insurance premiums compared to other providers at
0:45.0	health IQ.com slash twist. This format that we've started is called Open Office
0:52.0	Hours.
0:52.6	The concept is very simple.
0:54.8	Bring us your most pressing issue.
0:57.4	The thing that's the hardest for you.
0:59.8	And let's just brainstorm, workshop, possible solutions to whatever the problem is.
1:06.1	It's very easy to get busy as a founder and do the easy stuff.
1:10.6	And then avoid the difficult stuff.
1:13.0	What I like everybody to do during this session
1:16.3	is to just be really candid about what's not working.
1:19.7	What are you scared about?
1:21.5	What keeps you up at night? because we have a culture of everybody
1:24.4	wants to be crushing it and everything's up into the right having invested in
1:28.7	over 200 companies now I can tell you that is almost never the case.
1:33.0	And by the way, in life it's almost never the case.
	...

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