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 make 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:

• The Age of Excellence
• Is There a YCombinator Valuation Bubble or Not?
• The One Product that Makes Apple a Trillion-Dollar Company Overnight
• Mint.com-for-the-cloud Cloudability to Graduate from TechStars Cloud with 2k+ Customers
• Disrupting Education

FOLLOW ON TWITTER
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!

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, Yahoo CEO Scott Thompson, Kevin Rose and Zynga were among the hot topics in front of our panel of expert analysts–Niel Robertson, CEO of Trada, and Jon Ferrara, CEO of Nimble.

1:05 – 2:04  It’s This Week in Startups, it’s Friday and we’ve got a lot to discuss. The first thing we’re going to discuss is the Yahoo CEO.  Jon Ferrara, CEO of Nimble I am an investor, thank you for letting me in the round.
2:04 – 3:35 Do you do SEM stuff? At some point you’re going to want to turn on the paid funnel?
3:35 – 4:32 What does an SEM cost in major cities? At what point would Nimble say, it’s great to have a service like Trada but we need to bring SEM in house?
4:32-6:14 What’s the most successful client to date? Who are the most successful people in SEM and what are they selling?
6:17 – 7:18 Yahoo CEO Scott Thompson falsely claimed a computer science degree on his resume.
7:18 – 8:15 How big of a deal is this? Should he lose his job?
8:15 – 8:26 Jon: Someone should just take Yahoo in the back and shoot them in the head
8:48 – 9:58 People who lie and cheat in a system that is already rigged are idiots. It’s sociopathic in a way. In our industry there is absolutely no reason to lie. Going to college is considered a liability in the industry.
9:58 – 12:18 If you lie about this what else are you lying about? This is a fundamental trust issue. What do you think Niel?
12:18- 12:58  Niel: Supposedly I heard that he lobbied for the job. He begged for the job. Remember they hired him really fast? People who previously worked at PayPal hate that guy. I think this guy’s a bit of a disaster
12:58 – 14:00  Lon: Then how did he get this job?
14:00 – 15:15  Niel –  I think there’s somewhat of a trend. 10 years ago the best way to be a VC was to go to college with one and be their roommate.
15:15 – 15:42 Could you imagine going to the Winklevosses? They thought the cloud was going to be big in 2012, wow, great insight.
15:42 – 16:50 Discovery purchased Revision3. It was known for DiggNation. What is the advantage of taking on Rev3?
16:50 – 19:48 It’s not an epic sale, but it’s a single or a double and Discovery got a hell of a deal. If Digg Nation was still going it probably would’ve been a $50M sale.
19:48 – 21:31 If young people are starting on the web with free content, they’ll need to figure this out because niche content will work better than broad content. Discovery is a moneymaking machine.
21:31 – 23:18 One thing if you’re building these companies and you want to be protected, you need to have a good lawyer. eMinutes is a great company and helping entrepreneurs avoid making legal mistakes. eMinutes thank you for sponsoring the program. Everyone thank eMinutes.
23:18 – 24:01 Lon: Washington Post has purchased Digg. How long does Digg have? Will they continue to be a company after this? How does a buyout like this work?
24:01 – 24:48 When Kevin Rose finally writes his book it’s going to be amazing. In 60 days he sold Milk to Google, Revision3 to Discovery and Digg to washington post. It kind of feels like a Gowalla sale.
24:48 – 27:28 There’s something fishy going on here and I think there was a falling out. Greylock got their hands on both of these deals. What are your thoughts?
27:28 – 28:04 Let’s say the portfolio is either short or it’s long, that is going to factor into their decision making. What do you think Jon?
28:04 – 28:28 Jon: It really is sad and I was pretty sure Kevin wanted to sell so if the founders wanted to sell, then who didn’t want to sell?
28:28 – 29:04 How many uniques does Digg still have?
29:04 – 30:52 Where Digg tried to become more professional, Reddit just said screw it. They have jailbait. There’s some really offensive stuff on there.
30:52 – 33:21 Tumblr has an incredible array of porn and you know what I think, Instagram was built off of car models and strippers.
33:21 – 35:31 Lon: We’ll talk about the Kindle Fire. They’ve slipped from no. 2 to no. 3 in terms of market share. Why do you think this happened and what can they do to revitalize interest in the Kindle Fire?
35:31 – 36:00 The Android store really needs to get their billing right. The whole thing is a bit of a disaster. When it becomes $99 i think it’ll  do well
36:00 – 37:28 You guys have Kindle or iPad?
37:28 – 40:44 Lon: Zynga stock declined, leading many to speculate that OMGPop may be bringing the stock down. What do you think about this deal now? Did they overpay?
40:44 – 44:37 Zynga has also bought mid tier stuff too, and now they understand how this ecosystem works. Pincus can easily make his money back on every game but then the question is, is it a game that will last the test of time?
44:37 I have to ask Mark five times to be on the program. Why won’t you come on the program, Mark? Mark and I have an issue with our friendship now because he won’t be on the show
46:44 – 48:20 Tyler: So are you or aren’t you friends with Mark Pincus?
48:20 – 49:37 If you have one person who’s bringing it every day and then there are people who are showing up and not pulling their weight, then they should let them go, right?
49:37 – 55:07 Lon: LinkedIn plans to purchase SlideShare for $119M. Any thoughts on this deal? What kind of value is LinkedIn going to get?
55:07 – 56:31 You know one of the top things now will be the SlideShare of the day? The next step would be to have LinkedIn degrees.
56:31 They also, like Nimble are CRMish. Do you fear that they’re going to go full blown CRM?
57:55 – 59:43 Thanks to Lon for reading the news. Tyler, zero insights but you did have some good fact checking.
59:43 Thank you eMinutes!

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

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, first-time entrepreneur Michael Preysman joined Jason to discuss his disruptive play in the luxury clothing space. Everlane, Michael’s company, offers designer goods (think tees, sweatshirts, totes and ties) for under $100 in a thoughtfully curated, ever-changing collection.

1:00-3:30 Welcome everyone, with me today is Michael Preysman the co-founder of Everlane.
3:30-4:45 One of the things I’ve always been obsessive about is the perfect black tee shirt.
4:45-6:00 Thank you to Walker Corporate Law for their support of TWiST! Everyone thank @ScottEdWalker, then call Scott at 310-288-6667.
6:00-8:45 Found infographic on internet, not best one seen, but immediately pulled him in.
8:45-10:00 Michael: Fashion industry pricing is opaque. We went out there to be transparent and show true costs.
10:00-11:30 What made you want to get into this business?
11:30-14:00 Could you go even higher quality?
14:00-14:45 Who was in your angel round?
14:45-17:00 What is net promoter score?
17:00-20:30 What quantity do you have to produce the merchandise in in order to make the pricing work?
20:30-22:00 When we talked, I proposed that there’s an opportunity for a club, or some limited-access group. Any thought of that?
22:00-25:00 Thank you to Trada for sponsoring TWiST! Everyone give them a shoutout @Trada!
25:00-28:00 What impact do you think Everlane will have on Gap, American Apparel and the like?
28:00-29:30 Only idiots will buy retail ten years from now.
29:30-30:15 What kind of margin can you run this business at?
30:15-36:00 Why we don’t spend money on branding.
36:00-38:15 You’re into economics, right? What is your view on the efficiency of the world and the future of employment and commerce?
38:15-40:30 If retail goes away will we have a permanent unemployment reset?
40:30-41:30 What’s the hard part? What keeps you up at night?
41:30-44:30 Michael: Consistency and fabric quality are the differentiating factors for clothing.
44:30-45:30 Are you losing money on shipping?
45:30-48:00 How many people are in the company?
48:00-49:00 It feels like you’re building a radical loyalty, by being so responsive on social media?
49:00-53:00 Where do you see the company five years from now?
53:00-54:45 Could I be buying Everlane dress shoes five years from now that will be of comparable quality to anything I could buy at Barney’s?
54:45-1:00:00 Why hasn’t this been done before?
1:00:00-1:02:15 Michael, I wish you continued success. Everyone follow him @mpreysman on Twitter and follow @everlane.
1:02:15-1:04:00 We’re going to be sitting here in five years when this is a billion dollar company and I’ll be saying I told you so, Michael.
1:04:00-1:05:30 You’re not going to raise a round any time soon, are you?
1:05:30- Thank you to Trada and Walker Corporate Law for their support. See you all next time!

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

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

On This Week in Startups, Google Drive, CISPA, VC philanthropy and Klout were among the hot topics in front of our panel of expert analysts–William Quigley, a managing partner with Clearstone Ventures, and Sean Percival, ex-Mahalo-er and founder of Wittlebee.

1:00-2:30 Welcome everyone, we have a great panel today with William Quigley of Clearstone Ventures.
2:30-3:30 Also with us in entrepreneur Sean Percival. Sean, how many angels were in your A round for Wittlebee?
3:30-5:30 Thank you so much to eMinutes for their support! Everyone tweet their thanks @eminutes and contact them if you’re an entrepreneur looking to incorporate!
5:30-7:30 Let’s start with Google Drive, the long-awaited file storage and syncing system. Will these new conveniences mean that people are switching over en masse from Dropbox?
7:30-9:45 William: When Dropbox started, there were a few competitors, but every VC I spoke to thought of it as a commodity.
9:45-10:45 Sean, you’re a Dropbox user, will this sway you to switch?
10:45-12;30 Why wouldn’t you give ever Apple user the 100 gig free iCloud?
12:30-14:45 William, would you put your money on Dropbox today? Would you invest?
14:45-16:30 Why doesn’t Amazon have a drive that’s free to prime users and you have all your movies and all your books in
16:30-20:15 The controversial CISPA act was passed by the House yesterday. The bill is designed to facilitate sharing of information between private companies and the government over supposed cyber-security threats. If this passes the Senate, do you think Obama will veto it?
20:15-23:00 William: Why would all these companies who pretend to be pro-user roll over to the government? Is it fear of lawsuit?
23:00-25:45 Thank you to Trada for sponsoring TWIST! If you’re looking for SEM experts, check out Trada!
25:45-30:45 The six general partners of Andreessen Horowitz have pledged to give at least half of their income from their VC careers to philanthropic causes. Will this help offset negative VC stereotypes? William, as a VC, what do you think of this?
30:45-33:30 William: At my firm, we’ve decided that the termsheet needs to be blown up.
33:30-36:30 A few years ago, Sequoia Capital was talking about the fact that their LPs are from all these nonprofits and foundations and the money they were earning was going back into those charitable organizations.
36:30-38:00 William: You hear that, if you’re born in the US, you’re part of the global 1%.
38:00-39:30 The so-called “Instagram for video” startup Viddy raised a $30M seed round. Are people using this because of the known success of Instagram?
39:30-41:00 Would you invest in that, at that valuation?
41:00-43:30 Sean: This company is growing because they’re gating on Facebook, but that could change. And I don’t want to watch videos on Facebook.
43:30-46:00 Jason: I’ve tried to re-engage with Facebook but I just can’t get into it.
46:00-48:45 Sean introduces the concept of SMES (Social Media Entitlement Syndrome).
48:45-50:00 Jason gives advice on how to game your Klout score.
50:00-51:45 Lon introduces everyone to Klouchebag.
51:45-53:15 There’s a rumor going around that Microsoft might be interested in unloading Bing. Is there any interest from Facebook as a buyer?
53:15-59:15 Will Google come to this same conclusion about Google+ and eventually try to sell it?
59:15-1:03:15 In a recent Groupon staff meeting, CEO Andrew Mason let it slip that he may need to stop drinking so much beer. Do you think his immaturity is an issue for the business?
1:03:15-1:05:00 William: We recently hired an exec away from Groupon because he said, I don’t foresee an equity event in the next few years.
1:05:00-1:06:45 When I became a VP at Myspace, I stopped going to happy hour. Jason, what do you think about drinking in front of employees?
1:06:45- I think people dog Andrew a little bit too much. I guarantee that if they went to Google or Facebook right now, they would buy Groupon in a heartbeat if they were selling.
1:10:00-1:10:15 Thank you for tuning in everyone. And thank you to our friends at Trada and eMinutes for their support!
1:10:15-1:11:00 Sean, what’s the cost for Wittlebee? Everyone check it out at wittlebee.com.
1:11:00-1:11:3- William, thank you so much for coming on today and sharing your expertise. Same to you Lon, everyone check out Ranker.com. We’ll see you next time!

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