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Ryan Caldbeck Profile picture
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27 Jan, 6 tweets, 2 min read
Fantastic episode of the @RebootHQ podcast with @chaddickerson and @jerrycolonna

Two quick observations:

reboot.libsyn.com/140-from-heart…
1) I feel deep gratitude to Chad for being willing to open up about his experience. It would have been so easy to listen to advisors/PR folks and not talk about his genuine experience.
Him opening up I am sure has helped countless others normalize their own struggles.

That’s particularly generous given the incredible status he has earned. Thank you @chaddickerson
2) The story about @fredwilson and how he led during those moments at @Etsy is such an incredible display of empathetic leadership. To go to Chad (physically), to stand before the company and to own the decision. I found it really inspiring.
It’s a reminder to the younger generation that the best VCs aren’t just great stock pickers, but they are able to demonstrate real leadership in the hardest moments.
Loved it - thank you Jerry and Chad

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More from @ryan_caldbeck

Ryan Caldbeck Profile picture
31 Dec 20
1/ Equity crowdfunding or equity investment marketplaces failed. Full stop. Didn’t work.

Here is my synopsis on why the industry hasn’t taken off. Lots of reflection and painful lessons I hope others can learn from.
2/ Reason #1: The financial feedback loop for vc takes yrs. If you want one core reason the industry has not succeeded, it is this. Time between when an investor writes a check and gets confidence she should write again- is way too long to encourage repeat investment
3/ If you are ever at a YC event and some entrepreneur pitches you on a marketplace that helps private companies raise money…..ask how they will solve this issue.

[imagine being at a cocktail event again?]
Read 31 tweets
Ryan Caldbeck Profile picture
27 Dec 20
1/ “Unilever for the 21st century.” I’ve gotten that pitch almost 1x a week for the past few yrs. I believe in concept but haven’t seen the execution yet.

Here is what I think about the ideas and what I think still needs to be figured out.
2/ First - almost everyone I’ve seen has a similar pitch on the problem to be solved. Massive market with stale incumbents that can’t innovate, yet consumers demand innovation. Incumbents focused on profitability > R&D while consumers are asking for personalized products
3/ And so the enterprising founder sees a massive industry and stale incumbents and says “I can build Unilever for the 21st century. New fresh brands, build it first on d2c so I’m not encumbered by legacy brands or retailer relationships.”
Read 31 tweets
Ryan Caldbeck Profile picture
16 Nov 20
1/ VC efforts to build internal technology products continue to grow since I tweeted this in 2018. Most of those efforts are to influence perception of LPs or potential portfolio companies. Some are having impact. Here is my evaluation framework.

2/ First focus on the problem that is being solved by the data. Investing into tech for tech sake is dumb (that’s a real term). Let’s debundle the VC/PE process to identify what the job is, then evaluate where data/tech is likely to help:
3/
-Raising money
-Sourcing companies
-Evaluating companies
-Winning deals
-Post-close (waves hands)
Read 19 tweets
Ryan Caldbeck Profile picture
15 Oct 20
1/ Tuesday was my last day as CEO of @CircleUp. I’ve been CEO since starting the co. in 2011 with my co-founder @roryeakin.

This is a thread about what happened, why and my emotions about it. For more detail:

ryancaldbeck.medium.com/transitions-fa…

Much of this I have never talked about.
2/ My goals: I hope it helps founders feel less lonely than I did. Little public content about the challenges of transitioning exists, but I longed for it. I’m not here to provide a playbook- just to share my experience. Hope it might build greater empathy.

Here goes….
3/ Why: When I tell people that I’m transitioning to an Exec Chairman role their first question is always: “why?” Short answer: co. pivot + fertility issues + health issues + a false sense that grit was always the answer = burnout. Long answer: is longer so hang in there with me
Read 41 tweets
Ryan Caldbeck Profile picture
8 Jun 20
Great question @alessandroroco. First, we don't have all the answers and would love feedback and ideas.

We believe a core issue is lack of transparency. Removing info asymmetry will allow capital to move more freely & fairly.
1: Helio brings transparency to private markets- initially consumer. Helio captures long tail of innovation, identifying products before they're on the shelves of Whole Foods or Target or Sephora- so we don't have selection bias in only knowing about brands that have "made it."
Step 2 is proactively identifying underrepresented founders. An example: we track attributes. We're able to find all the brands in a given category that self-identify with certain attributes- which could include minority-owned.
Read 4 tweets
Ryan Caldbeck Profile picture
22 May 20
1/ Lots of challenges and opportunities that get catalyzed by COVID-19. As we transition into a new normal, I’ve wanted to rethink a few parts of our strategy, structure and process - including things like norms and how we evaluate performance.
2/ In this state of uncertainty, how certain are we about how we currently measure success? Historically I’ve thought about measuring Inputs v. Outputs.
3/ To level set, Input goals are levers that drive Output goals:

-Sales: Close 3 new customers or bring in $1m in revenue (output) BY cold calling 50 customers this month (input)
-Product: Improve conversion rate by 5% (O) BY interviewing 10 customers to improve cust exp (I)
Read 24 tweets

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