Tweener Fund Resources (August 2023)

August 28, 2023
Scot Wingo

(Periodically we'll repost the email we send to our Tweener Fund portfolio CEOs minus some of the "CEO exclusive" material left out)

We got a strong positive response to the last note with some unique startup-oriented resources, so plan to send these out no more than once every 30 days or so when we have a batch of interesting things for you to chew on.

Today, the lead piece of content was stirred up by Plum CoOwnership CEO Matt Williamson who is considering starting a podcast.  I also threw in a couple of other interesting items/reads I discovered recently that maybe interesting to you as well - my goal is to surface content you probably haven't seen, helps you think about scaling or something relatively strategic and adds value.

The podcast/content marketing strategy topic has come up probably 10 times lately with various portfolio CEOs and I thought we'd zoom it up so you guys could 'listen in' on the convo and think about content marketing, podcasting, etc.  Note IMHO this cuts across all categories, stages and b2b/b2c and hopefully it stimulates some ideas on how you can elevate your content strategy, or more popularly called inbound marketing these days.


o Zoom  on content marketing strategy and then we go deep on podcasting - PortCo's RepVue and GreenPlaces get shout outs as best practice examples (meaty topic ~1hr)

o Update on a very interesting real estate coworking trend (4mins)

o Excellent Ben Horowitz pod (wartime/peacetime CEO) (35mins)

o Elon's 5 steps for better design (process/products/whatever) < 3mins {{this is gold}}

o Brian Chesky (AirBNB CEO) on elevating your CX < 4mins

o How to slow down time for your org. est time unknown, i'm still working on grokking this

-------- Content Marketing/Podcasting Fireside chat with Matt @ Plum -----------

Exclusive Tweener Fund CEO content....

-------- Real Estate Coworking -----------

Tweener Fund has received 3-4 inbounds from large commercial real estate (office space) players in the Triangle- they have a lot of occupancy and want startups in their buildings, how can we partner?

Last week we toured several spaces available in a building in downtown Raleigh with ~5 portfolio companies.

The feedback on the portco side is:

o Coworking is getting very expensive and 'full'.

o We're too small for traditional real estate offerings -e.g. we don't need 5k sq-ft for 10yrs.

It looks like the 'need' is for a new way to think about coworking.  Maybe there's an equity component (e.g. trade rent for a warrant type thing), maybe there's more of a Tweener shared space that is super flex and open - something like that.

We're taking this feedback to the big space players and we'll keep you posted if something comes of it, my spidey sense suggests there is a deal to be done there, stay tuned.

In a perfect world we'd have novel Tweener fund coworking spaces across the Triangle, we're not there yet, but the idea intrigues us, especially if it comes with insanely great value to portcos.

----Ben Horowitz pod---------------

A game changer book for me is now 10yr old, The Hard thing about Hard things -I've probably already recommended it to you all already, but if not, pause here and go read that.

Ok, welcome back, Ben did a great pod (I can only find the iOS link) on my favorite chapter - wartime/peacetime ceo and added a lot of good nuance to it, here->

---------Elon's 5 tips---------

I'm a pretty hard-core Elon nerd (I had to resist including the 45min FSD demo here) and this was a great short clip from 2yrs ago I hadn't seen before that I wish I had heard before, We're at $70m ARR at Spiffy and hitting a new set of scaling/process issues and Elon nails the sequence and culture it takes to punch through that.  This is equally helpful if you are on either side of PMF->

---------Chesky on CX---------

I was late to realizing Chesky is such an awesome public speaker and saw him masterfully handle a really hard CNBC interview and have been slowly trying to check out some of his other content.  Someone shared this great snippet where he was at a show explaining how they elevate the CX at AirBNB. If you are a CEO not spending a chunk of your time thinking about the CX (yes also B2B), you need to make time for it, this will maybe give you some inspo->

-------Make time slow down for your org------

At ChannelAdvisor, as we got to each milestone( $10m , $20m, $50m, $100m, etc ), I noticed that we were going slower and slower as an org.  A new feature would take 6 months that previously we could bang out in a week - WTF!  That inspired me to think more about how orgs are setup.  This sounds like a 'in 2yr from now prob' to you if you are earlier, but I've also found the decisions you make today, plant the seeds for this and become increasingly hard to reverse or change, so it bears a little bit of thought (e.g. 2hrs on a weekend) today.

This paper is dense and academic, but introduces some new ways of thinking about how to structure your org that I've found valuable.  I like to pair it with my favorite Amazon book (Think LIke Amazon) which gets to a similar place - the TL;DR is your company should morph into a collection of somewhat independent startups as you scale with some shared resources, but some duplication.

This article helps you think through - should I go deeper or wider? And basically if you can set  it up right, your company can execute 2-3x faster than competitors and incumbents (slow down time) and that gives you a huge edge->

Of course, Amazon inevitably comes up here as they are the one big org that has, so far, not fallen under it's own weight.  (fun fact, Amazon has 1.3m employees)

That's it for this 30 days, I hope you enjoy some of these resources as much as I did,


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