E255: All Ask Jason on This Week in Startups



about this episode

Click here to stream the audio version of this episode.

Join our mailing list and be the first to learn about upcoming guests!

On This Week in Startups, Uncle Jason lent a helping ear to startup founders in need of advice. Five founders called in to ask questions regarding their most pressing career and business issues — from how to reposition a company, to the pitfalls of taking strategic investments

0:00 Today on This Week in Startups, it’s our Ask Jason episode.
01:10 – 3:23 Hello everybody. You’re probably listening to this while running, driving on the freeway. I’m using my NPR voice. I’m here with Tyler Crowley and today we’re going to talk about sexism at Whole Foods.
03:23 -5:08 eMinutes is passionate about helping entrepreneurs
05:08 Paul Secor has a question about how to get the best exposure for his company, Sports Birdy. He also wants to know if he should focus on building the best network or building a revenue stream
06:08 – 7:33 Jason: Should you go with revenue or go with building audience? You should wait to perfect the product. Certainly the people who would buy those filtered apps around photos where they had to pay, those only got a few members. I’m a big fan of just starting with getting an audience
07:33 – 7:55 Tyler: the reason we do two episodes a week is because of advertisers.
7:55 – 8:39 Jason: It’s best to wait for the demand. I’ve seen a lot of peoplel who want to do a business like that where they capture all of the tweets. It was a good idea but it didn’t get funded
08:39 – 8:54 Tyler: It depends on what resources you have in a way, how tight you are with investors.
08:54 Jason: You didn’t take investment for Skweal.
9:29 – 10:16 Tyler: I think everybody looks at what resources you have and how do you play that hand. I had incredibly cheap development cost. I also had incredibly good hookup on support and an incredibly good hookup on sales help.
10:16 – 10:26 Tyler: Had I raised money, it would’ve been a completely different game in many ways
10:26 – 11:11 Jason: It’s best to make it a passion project until it turns into something more. When we first operated, we didn’t have the pressure of overhead
11:11 – 11:36 Paul:  I guess should I go after the halo effect and try to get some tech guys who are big NFL fans?
11:36 Jason: There’s an even easier way. Either end of the spectrum, you’re going to be going into an email inbox with hundreds of emails a day and it’ll get lost. You want to basically pull them in, you want to seduce them in. How many views do you have?
14:06 – 14:10 Paul: The most is 700 so far
14:10 Jason: Ok, that’s not too bad. You have to learn how to game youtube, learn the best practices. You’re just going to have to start learning that ecosystem and the tricks in it.
15:08 – 15:43 Tyler: You reach out to gary and Jason and anyone else who is passionate about a team and i want to ask you on Twitter, who do you think will win thiss week between two particular teams.
15:43 – 15:58: Jason: Ask a question first, upon asking a question, people feel determined to answer a question
15:58 – 16:09 Tyler: You want to essentially get them to participate in your show by being on the record
16:09 – 17:01: Jason: It’s called the reciprocation effect
17:01 – 18:24: Jason: Ok, next caller. is this Daniel?
18:24 – 20:14: Daniel: We’re in the middle of a pivot with Talkchalk, while Soapbox has recently gained a lot of traction, so my question is, do we take a tech company that might have hockey stick growth or slow steady growth over time?
20:14 – 21:26: Jason: This is hard because I’ve been there. I’ve come to the conclusion that you should do what makes you happy in life. If you feel that you can’t be successful at both, then certainly, focus on one. Why don’t one of you become the CEO of one and one become the CEO of the other?
21:26 – 22:13 Daniel: My co-founder, Dave, left his full time job as a TFA core member. I held out  a little longer. We’re basically living off of savings. It’s come to the point where we do need to raise a round in either one or both.
22:13 – 22:31: Jason: If you self-rated yourself on scale of 1-10 how awesome of a job are you doing on Soapbox versus Talkchalk
22:31 – 22:44: Daniel: Overall, i think we’re doing pretty well. We have great teams behind both.
22:44 – 22:57: Jason: You have to be objective with yourself if you want to make progress
22:57 – 23:00: We’re probably about an eight in each
23:00 – 23:07: Jason: No eights
23:07 – 23:20: Daniel: Probably a nine in soapbox and a seven in Talkchalk
23:20 – 24:50  Jason: It looks like Soapbox is closer to the finish line and the other one will take a lot more capital. You have to choose if you want to swing for the fences and try to do something extremely hard.
24:50 – 25:45: Jason: Talkchalk is going to require 100% of your attention.
25:45 – 27:15: Jason: I have recently gotten hyper-focused. At this point in my career, I can fund things no problem and I can staff them pretty well, too. You have to know how many resources you have.
27:15 – 29:48: Tyler: I like Soapbox. It feels cleaner.
29:48 – 32:13: Ad for MailChimp
32:13 – 33:40 Jason: This business has a lot of soul and it has a great mission.
33:40 – 34:34 Daniel: Can I offer a discount to your TWiST followers. Promo code: twist10
34:34 – 35:33  Richard White from UserVoice: My question is about positioning. We get a lot of people saying that they don’t know about our new product HelpDesk. The challenge is how do we get the word out that our company has now evolved?
35:33 – 36:28 Jason: Basically you’re suffering from the success of your first business.
36:28 – 37:09 Richard: The HelpDesk product is so complimentary. When we surveyed people signing up for free trials, 75% of them were looking for an all in one solution.
37:09 – 37:20 Jason: i assume helpdesk software is doing well. Is it doing better than the feedback product?
37:20 – 37:46 Richard: It’s hard to say one’s better than the other but combined it’s doing better
37:46 Jason: I wonder if making the user voice product free for life and then just saying we’re HelpDesk and feedback is the free product.
39:10 – 40:30  Jason: to take over the voice of the industry. if it’s me, i’m doing the help desk summit. this week in help desk, omg that show would be incredible. uservoice to me as a brand is out there doing its work, but i don’t see them as a brand leader. you have the opportunity to be a brand leader
40:30 – 40:55: Richard: We’ll do a twist30 promo code
40:55 – 41:00: Jason: Where do you go to get your HelpDesk media?
41:00 – 42:27: Richard: We have a really good blog and have talked about consolidating that.
42:27 – 44:31: Jason: you’re about customer support issues. consumer nurturing, become the opinion leader on that.
44:31 – 44:43:  Tyler: I want to hear what the next guys promo code is
44:43 – 44:53: Jason: Next up is michael, but what did you think about UserVoice?
44:53 – 47:17: Tyler: It’s similar when an actor starts wanting to be a musician.
47:17 – 47:25: Jason either embrace your past or hide from it.
47:25 – 48:27: Our next caller Michael Fern of Intigi. He has a question about the importance of building native iOS and Android apps as a bootstrapped startup with a B2B web app
48:27 – 50:45 Jason: What most people are saying now is the future is mobile and if you want to get engagement, if you come out mobile first, those chances increase. If I see a website, I’m kind of saying, ok, you’re stuck in the last paradigm.
50:45 – 51:01: Michael: At this point, we’re not pulling that much data into the results page. We want you to be able to preview the article
51:01 – 51:32: Jason: For me, if i trust the source, if this has been tweeted by these people, did you build this for the marketers?
51:32 Michael: Yes, it’s targeted towards marketers
51:38 – 52:30: Jason: Have you thought about using this tech to auto-post about feeds that post to specific verticals?
52:30 – 52:47: Michael: We have that tech built. The automated tech is possible.
52:47 – 53:18: Jason: maybe you should just become the weblogs inc of tweeting
53:18 – 53:31: Michael: We’re emphasizing right now marketers bringing value to the tweets
53:31 – 55:35: Jason: I highly recommend it not being time-based. You have to have an iOS app to make this work. Go with mockups to angel investors, and tell them people want it but they just need funding. Have you asked your users about iOS?
55:35 – 56:40: Michael: we haven’t asked that specific question yet
56:40 – 56:56: Jason: How is it funded to date?
56:56 – 57:10 Michael: We’ve raised $35K
57:10 – 57:36 Jason: It’s really good stuff. I think there’s a business here but don’t think you’ve reached it yet. Who’s your top paying customer and/or most active?
57:36 – 58:18: Richard: Personal marketers with a freelance business, startup marketers, like a CEO or VP marketer and then we’re working with marketing agencies that do marketing for hundreds of clients
58:18 – 59:31: Jason: It’s very powerful technology. If you get this right, you might want to make it only available to the elite people and they’re willing to pay you $2K times the price in order to online casinomake sure civilians don’t have it.
59:31 – 59:47: Jason: Where did you come up with this terrible name that no one can pronounce?
59:47 – 1:00:01: Michael: It’s a mashup of a few different words.
1:00:01 – 1:01:30: Jason: Your first name is always going to be terrible.
1:01:30 – 1:02:00 Jesse Maddox with TripLingo: I actually made one of our apps free. Search for TripLingo to get the romance version for free. My question is, how do we think about taking strategic investment as an early stage startup? How early is too early?
1:02:00 – 1:07:27: Jason: Strategic investment is very dangerous. They can be meddlers, information suckers and price insensitive because of those two reasons
1:07:27 – 1:07:36:  Jesse: So no blocking provisions
1:07:36 – 1:10:47 Jason: Limited information rights. You’ll see strategics invest in a good entrepreneur because they want to have access to them and show a vote of confidence early and then they get a heads-up on the sale.
1:10:47 – 1:12:07  Tyler: VCs generally don’t like it when you have strategics
1:12:07 – 1:12:52 Every one check out TripLingo. Thank you
1:12:52 – 1:14:00 Jason: Go to twistlist.co. You’ve earned the right to join the list
1:14:00 – 1:14:30 Namaste. RIP MCA, Beastie Boys for life, peace out.

Support This Week in Startups and independent media by joining the TWiST Producer Program at TwistList.co!

Want to support TWiST another way? Use bit.ly/twistamazon when you shop and a portion of your purchase will go toward helping keep independent media like TWiST on air!

Keep up with the latest from our sister company, LAUNCH:

Jason: @jason
Tyler: @steepdecline
MailChimp: @MailChimp
eMinutes: @eMinutes

Support This Week in Startups and independent media by joining the TWiST Producer Program at TwistList.co!

Multilingual? Translate this episode of TWiST into another language and email the transcript to translate@thisweekin.com

Keep up with the latest from our sister company, LAUNCH:

Jason: @jason
Tyler: @steepdecline
MailChimp: @mailchimp
eMinutes: @eminutes

Special thanks to the members of the TWiST Backchannel Program!

Executive Producers


Associate Producers

  • Brad Pineau
  • Kat Ganesan
  • Nicholas Christian
  • Mau Frontier
  • Kyle Braatz
  • Serena Ehrlich
  • JD
  • Alex Lotoczko
  • James Kennedy
  • Benoit Curdy
  • Asher Nevins
  • Mike Kaltschnee
  • William Doom
  • David Lee
  • Jake Kerber
  • Sarp Coskun
  • Giuseppe Taibi
  • Tyrone Rubin
  • Keno Vigil
  • Paul Peters
  • Jamal Waring
  • Nick Ostroff
  • Alex Binkley
  • John MP Knox
  • Bryan McCormick
  • Marcos Trinidad
  • Allen Cordrey
  • Daniel Mich
  • Joshua Rosen
  • Grant Carlile
  • James Smith
  • Christopher Rill
  • Elliot Myhre
  • Nihon Giga
  • Nathan Gielis
  • Greg Meadows
  • Rick Cartwright
  • Jacques Struwig
  • Robert Ward
  • Adam Gering


  • Ryan Hoover
  • Michael Cranston
  • Josiah Thomas
  • João Fernandes
  • Petrus Theron
  • Michael Wild
  • Dale Emmons
  • Tim de Jardine
  • Alejandro Vasquez
  • Milan Babuskov
  • Chris Rowe
  • Nelson Melo
  • James Dawson
  • Toddy Mladenov
  • Daniel Torres
  • Chris Macke
  • Piotr Zuralski
  • Armand Konan
  • Brian Vogel
  • Paul D
  • Jennifer Sun
  • David Kolb
  • Sue Marrone
  • Eugene Granovksy
  • Will Blackton
  • Ryan Dodds
  • Brett Arp
  • Jason Cresswell
  • Edwin Orange
  • Daniel Bradley
  • Shawn Daniel
  • Priidu Kull
  • Patrick Desroches
  • Alex Lam
  • Paul Secor
  • Ryan Urabe
  • Madhu R.
  • Paul Ardeleanu
  • Ian Thomas
  • Manny Alarcon
  • Charlie Osmond
  • Christopher Smitley
  • Roshan H.
  • Barcy Cordrey
  • Matt Beaubien
  • Matthew Smith
  • Oscar Bueno
  • Tim Hoyt
  • Ian Gerstel
  • Taphon Maddison
  • John Bradley
  • Luigi Armogida
  • Dave Ferrara
  • Janus Lindau
  • Chris Mancil
  • TR Ludwig
  • Giles Thomas
  • Jason Cartwright
  • Michael Del Borrello
  • Joshua Rosen
  • David Karlberg
  • Marcus Schappi
  • Justin Furniss
  • Mike Hauck
  • Jess Bachman
  • Isaac Hill
  • Robert Haydock
  • Dan Sfera
  • Flaviu Simihaian
  • Kiko Cherman
  • Chandra Siva
  • Kasper Andkjaer
  • Zach Woodward
  • Chris Galasso
  • Chad Olsen
  • Michael Grabham
  • John Shiple
  • Gregory Hoffman
  • Chris Rickard
  • Eskil Steenberg


more episodes