Glenn Kelman CEO of Redfin | E1261

00:00 Intro- Glenn Kelman from Redfin
01:25 How Jason and Glenn met
03:11 Jason’s experiences with being approached in public
05:05 Glenn’s take on the housing current situation
08:02 The impacts of WFH on the housing industry
09:25 Why investing in housing could have been the solution to high prices
11:07 Indochino- Get $50 off of $399 or more by using code TWIST at
12:35 Effects of building more housing as a way to limit home price appreciation
16:26 The argument on density being better for progressive’s neighborhoods
19:09 Areas that are pro-development and are booming because of it
21:00 Canada as a progressive area for housing and tech workers
23:43 Glen’s thoughts on San Francisco as a livable city and office location
26:50 Calm- Get one month free after attending a free demo when you go to
28:22 Discussion around putting efforts into office buildings and working from them
32:54 Jason asks Glen what companies lost from staying in a work from home setting
35:24 A discussion around work-life balance and generational differences
38:15 Notion- Use TWIST to get $250 off an annual team plan at
39:53 Jason on debt and Glen on the cynicism of capitalism and its impacts on housing
42:22 The difference in lifestyle when having $100M vs $100B
46:52 Redfin, employing their own agents full time and other changes to improve efficiency
55:13 Jason asks Glen what it was like for Redfin to go from struggle to success
58:33 Glen and Jason discuss a controversial topic covering the DOJ and MLS
1:03:03 Nondisclosure states and why people still use listing agents
1:05:20 A breakdown of the DOJ case with the National Association of Realtors
1:10:17 The impacts of speaking to reporters and the press as an entrepreneur

Check out Redfin:


How Allen Chen Built a Globally Scalable Fitness Trainer | E1259

Episode Here:

00:00 Intro Allen Chen, CEO of Fitbod
01:06 How Allen and Jason met
05:11 Fitbod Origins
08:19 Fitbods approach to connecting with customers
10:31 Organic Growth vs Paid Growth
11:42 LinkedIn – Post your first job for free at
13:15 The secret to paid marketing
15:33 Fitbod’s history of onboarding and their revamp
17:44 The importance of gaining a users trust
20:12 Allen being the ideal customer profile for Fitbod
21:33 Allen’s advice on having a strong funnel and finding the right audience
24:10 Odoo – Get your first app free and a $1000 credit at
25:22 The outlook on affiliate, influencer, and referral marketing
29:14 The plan to jump from 225K paying customers to 3x revenue
31:27 Jason explains his term “pegasus” and how it relates to Fitbod
33:42 Allen covers Fitbod’s opportunities for raising in the future
35:05 Jason gives Allen an “unsolicited offer publically” of $5M
35:42 Bubble – Get one month free of a no-code plan at
37:11 Allen asks Jason advice on getting his team to see liquidity
44:48 Jason explains the advantages of a corporate buyback and options to skip dilutions
46:30 Fitbod is hiring across all positions
48:35 Allen’s experience with YC

Check out Fitbod:
FOLLOW Allen Chen:

How to start a new Venture Capital Fund with Acquired.FM | E1258

00:00 Intro Ben & David from Acquired
00:56 David’s new fund Kindergarten Ventures fund
14:45 The costs of operating a fund & how David is doing it
18:49 Why LPs care about pro-rata
25:29 The scale of Jason’s syndicate & value VCs bring
30:17 Jason’s preemptive pro-rata strategy (Sequoia does this too)
35:50 The podcast strategy
39:23 Why All-In works
43:15 Jason’s investing goals
52:39 VC scout programs
56:11 The Mount Rushmore of Venture Capital

Talking Duolingo, Robinhood, China and more with Alex Wilhelm | E1257

Subscribe to This Week in Startups on Apple:

00:00 Alex Wilhelm from TechCrunch
00:45 Intro
03:40 IPO dynamics: Robinhood & Duolingo
12:34 Linode – Receive a $100 cloud credit at
14:04 Robinhood IPO, what’s the strength of the business?
20:53 Duolingo the success of DTC edtech
23:35 LinkedIn Jobs – Post your first job for free at
25:09 Can consumer subscriptions continue to succeed
28:25 Google’s growth (at what cost)
33:05 Why companies are more efficient early on
37:24 Masterworks – Skip the waitlist at to invest in art using promo code TWIST at
38:51 Startup fundraising environment
42:46 Amazon’s rapid growth
47:35 China’s actions on Tech & Bitcoin
1:04:19 Apple talk
1:12:32 Why tech companies are vertically integrating
1:14:05 Digital Acceleration & going back to work

Check out TechCrunch:


How to Manage Influencer Marketing with GRIN CEO Brandon Brown | E1256

Subscribe to This Week in Startups on Apple:

00:00 Intro – Nikola, Robinhood & Brandon Brown from Grin
01:50 News – Trevor Milton indicted for fraud at Nikola
12:12 Pipe – Start trading your companies recurring revenue for cash now, free for 12 months at
13:23 Lessons for investors
18:55 Robinhood IPO today
24:10 Twilio – Get $500 in credits at Sign-up now at
25:43 Interview – Brandon Brown, CEO of GRIN
27:48 Why influencer marketing works
37:20 Embroker – Get an extra 10% insurance for your business at
39:00 What influencers earn with partnerships
43:13 How companies use GRIN
51:04 How brands run large scale creator programs
54:19 How advertising is evolving

Check out GRIN:

FOLLOW Brandon:

Devin Finzer, CEO of OpenSea the NFT Marketplace | E1255

We had a chance to chat with a leader in the NFT space, powering $170M+ in transactions a month.

00:00 Intro – Google earnings & Devin Finzer
03:22 News – Google’s earnings
12:22 Drata – Get 15% off your SOCS2 and waived implementation fees at
13:48 YouTube’s ad growth
19:16 Google’s return to work policy
25:30 LinkedIn Jobs – Go to to post your first job for free
27:01 Interview – Devin Finzer, CEO of OpenSea
36:47 Odoo – Your first app is free forever get a $1000 credit at
37:58 How NFTs moved into the main stream
49:20 How OpenSea manages authenticity on the marketplace
54:25 What NFTs will look like in 10 years

TWIST Episode 1251, China punishes Didi, Twitter’s new feature, UAE makes it rain + Do Kwon of Terraform Labs

I cover China’s increasing penalties for Didi , Twitter’s test of a downvote feature, and how the UAE was able to induce rain with electricity. Then Do Kwon, the founder of Terraform labs joins to discuss his stable coin project TerraUSD, the underlying cryptocurrency LUNA, and shed light on Tether as crypto insider.

00:00 Start
02:52 News – China increases the pressure on Didi for “data privacy”
10:33 Dell – Sign up for a free IT consultation and a 5% off coupon at
12:13 Twitter tests up/down voting tweets
17:32 UAE figures out how to make it rain with electricity
21:02 Notion – Go to and use promo code TWIST to get $250 off the annual team plan
22:38 Interview – Do Kwon of Terraform Labs
27:14 Why you can’t build decentralized finance with centralized stable coins
31:18 What is an algorithmic stable coin?
35:26 Vanta – Automate your SOC 2 report, get $1,000 off at
37:02 Why did Terra’s price fluctuate as a stable coin?
43:46 What Do thinks China’s strategy is re: crypto
59:56 What is going on with Tether?

Social Media Addiction: Why I’m taking a Twitter break

For the second time in the past five years, I’ve decided to take a break from Twitter.

I’m a functional Twitter addict, getting all of my work done and maintaining important relationships while spending far too much time on the platform. 

When I wake up, I check Twitter before my email and Slack.

Before I go to bed, I thrash among Twitter, podcasts, audiobooks, and playing chess.  

All day long, be it a workday, the weekend, or on vacation, I’m sucked into my replies, trending topics, and Twitter feed. 

I love it, but sometimes I love it too much. 

While I don’t regret the time spent there, it is a blocker to getting other things done, and while it’s worth it on so many levels, the truth is it can put even the most optimistic person in a foul mood. 

The amount of trolling and dunking, which can be entertaining, can sometimes become exhausting. 

So, I decided this week to focus on two media channels for the rest of the year: my podcasts and my next book. 

I’m still checking Twitter, and I will retweet things and like them, but I’m not going to reply to folks OR start new tweets. 

I will automate the sharing of podcast episodes and blog posts to Twitter, so folks know when new content lands, but for now, I’m going to clear my mind and focus on getting my passion — This Week in Startups — to consistently publishing 5x a week. 

Oh yeah, I also do the All in Podcast weekly now, so that means I’m doing six podcasts most weeks. 

Now, for most humans, six podcasts a week seems like a lot, but for me, it’s like going to lunch or dinner six times a week with the most exciting people in the world — in other words, it’s nothing. 

That’s a lot of cognitive work.

My current plan is to take the rest of the year off Twitter and focus on the podcasts (TWIST & All In) and the book while growing my two startups, and the LAUNCH fund. 

The last time I took off six months, I got the book ANGEL done, traveled the world to support it, and that little niche book sold tens of thousands of copies and was translated into 10+ languages … and my angel investing club ( grew from 1,000 members to 8,000. 

So, it’s time to write the book. I’m not ready to talk about the details yet (and I haven’t even sold it), but it’s going to be a barn burner.

Candidly, I’m more excited with you reading the book in the spring of 2022 than I am getting using Twitter right now. So, I’m going to follow my heart.   

best Jason

Note: I did a short audio piece on this decision last night on

Rad Power Bike Review: it’s fun!

On 2021 startup valuations

Some folks in our angel investing club ( have asked me for my thoughts on the surge in early-stage valuations.

The market is scorching hot, with startups across all growth stages getting funded faster and at higher valuations. 

[ Click to Tweet (can edit before sending): ]

The dollar amounts raised are often staggering, but so are the exits — which are driving this.

When there is a large number of meaningful exits — from Uber to Airbnb to Coinbase — investors get enthusiastic about investing in the next wave of unicorns.

This causes valuations to quickly double and triple, with investors reporting, “the valuation doesn’t matter if this becomes the next unicorn!”

Of course, it does matter since most companies go to zero, and you can invest in three startups at a $10m valuation for the same price you would pay for one at $30m. 

Three swings at bat dramatically increases your chances of hitting an outlier.

Now, if you could invest in Uber or Airbnb’s angel round, Series A, or Series B, you would certainly do it, but there is no way to know which startup is the next Uber or Airbnb (at least not with certainty). 

Our firm and investment club are adjusting to this moment to focus on four things:

  1. We are investing in high-quality startups at reasonable prices, as we have always done. 
  2. We are investing in select, very high-quality startups at these higher valuations. 
  3. We are helping existing portfolio companies raise money during this frothy market.
  4. We are meeting with as many startups as possible and noting when we pass because of the valuation so that we can meet with them again in the future. Many times a startup will “catch up” to a high valuation, and the next round will allow us to engage at a more defensible valuation. 

We invested in Calm, Uber, and Thumbtack for ~$15m — combined. 

While the $5m Seed round may be over for now, we have seen several pre-launch startups command $15m to $50m valuations. If those startups are led by a serial founder, it’s justifiable, but most of the time, they are first-time founders. 

We are content to sit out these Seed rounds and wait to see if the startup gets to product-market fit. If a pre-launch startup raises at a $50m valuation, for example, and then gets product-market fit and hits $1m in yearly revenue, the valuation is likely to be $10-25m in a normal market. 

This “filling in the valuation” strategy is acceptable for founders who have discipline, but it does carry the obvious risks of a down round if they don’t. Most founders seem to understand this, with many telling me, “I know this valuation is crazy, but we are taking advantage of this moment.” I would do the same if I were them, so no judgments — just make sure that you have the runway to fill in that valuation. 

For investors, you don’t have to hit every winner to be a big winner. In fact, you only need to hit one. 

In a hot market like today’s, we encourage members of our investment club to evaluate their goals, pace themselves, consider making adjustments to their strategy, and always remain disciplined — by focusing on great founders, quality products, and delighted customers.

Great founders.

Quality products. 

Delighted customers. 

Those things don’t happen by accident. 

Best, Jason
PS – Join us next week for Meet Our Fund, where 25 venture funds are pitching thousands of founders