Ryan Caldbeck
@ryan_caldbeck
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Founder, CEO, Board Member Starting something new
Joined August 2015
1/ In honor of all the CEOs who have told me they are "crushing it," and that they “can’t keep up with the growth” - I’d like to put forward just some of the many many mistakes I’ve made as CEO. Some were bad for @CircleUp , some were just embarrassing:.
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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: . . Much of this I have never talked about.
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1/ I believe there are things that CEOs almost universally feel, but are afraid to talk about, making this journey as a CEO lonelier and less healthy. I recently had an amazing dialogue with some other CEOs about these topics. I wanted to broaden the conversation publicly.
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1/ A picture is worth a thousand words. And to me, an x-y is worth a million. Here are some things I believe to be true based on my experience as a CEO and investor. Some or all may be completely wrong.
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1/ Everyone in consumer is trying to figure out how to play emerging CPG (<$15m in revenue). EVERYONE. Every public CPG company, every retailer, every consumer VC and PE firm, every meaningful public investor. EVERYONE. Here is why.
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1/ We Pivoted a few yrs ago. This is the story- mostly my feelings. It has never been told publicly. This will be rambly and represents the chaos in my head at the time. There is [hopefully] no advice here. I don’t know if we did it right.
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When a CEO/founder says "culture is the most important thing", it's really hard to understand how true that is until you've been a CEO/founder. Learning that culture is the most important thing is probably the most important lesson I've learned as a CEO.
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1/ How to get promoted at a startup:. At larger companies career tracks are (too) well defined, and there are clear paths on how to move up. But at startups there isn’t a playbook for how to get promoted.
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Am I the only human that is amazed that @Gmail hasn’t figured out how to more effectively notify users that your fonts are jacked up when you send an email that has different font sizes/styles? That feels like a solvable problem in 2018 to help users not look like clowns.
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11/ I heard so many times “if you are thinking about firing someone the decision has already been made.” That is correct.
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Most underreported story in sports over the past 15 years.
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9/ ….a quote from Howard Schultz I really like: “One of the fundamental aspects of leadership, I realized more and more, is the ability to instill confidence in others when you yourself are feeling insecure.”.
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5/ Turns out that proactive thoughtful thank you emails to VCs come off as desperate, not courteous. Many VCs sadly view it as a negative signal that the Co. isn't hot (or else why would the CEO being taking the time to send the note). I hate that because I love thank you notes.
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8/ Took ~27 phone calls from cold calling recruiters who claimed they had “a Rock Star engineer at Google that wanted to work for CircleUp.” “Rock Star engineers from Google” neither work with recruiters that cold call companies nor people that say “Rock Star engineers”.
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The lack of alignment around how men socially say hi/goodbye to each other is just amazing. Hand shake, half hug after the hand slap, fist bump, full on hug. 80% of the time I do the wrong thing. Totally stresses me out 20 minutes in advance.
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I’ve worked with some great board members and some horrible ones for startups. Bad Board Member (BBM) v. Good Board Member (GBM). Stealing format from @bhorowitz. 1/ BBM will always say “let’s do that too.” GBM recognizes resources are finite and encourages focus.
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One of our companies just got a term sheet from a $100m vc fund that wants to charge the co. quarterly monitoring fees. To a startup. I find that simply disgusting.
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1/ Founder compensation. I’ve had conversations with 5-10 tech founders over past 2 months about their comp and the awkward conversations they have with their board about the topic. Here I’ll hit on cash comp, equity refresh and secondary. Dangerous and uncomfy topics. Giddy-up.
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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.
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1/ I think a CEOs job boils down to 3 things:. -set and evangelize the vision .-attract and retain talent.-don't run out of money. That's my framework.
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1/ There are products/resources that I wish I had found much earlier in my journey as a CEO/founder. Here are some of the most valuable. [Like always I’m not an investor/advisor in any unless noted.].
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Talked with a founder this morning about their raise. A VC (@a16z) passed and he spent 5 minutes raving about them and the way they passed. They gave him super detailed feedback that was actionable.
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9/ Took me 2.5 yrs to find this: (lots of related posts on AVC) Thanks @fredwilson. Grant equity in $ not %. .
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7/ Talent> 1 yr+ in I hadn’t crystalised hiring reqs for the co (horsepwr, work ethic, and integrity). Hiring managers can go rogue w/o a shared framework and assessment criteria. Frameworks help people row in the same direction. I eventually wrote this:
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20/ I obsessed over some fancy UIs that we never actually used (or we used and they didn't matter). MVPs are the way to go. And UIs are nothing without the U.
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24/ Take time to meet with other CEOs where you both can be vulnerable. It is incredibly cathartic to talk about what isn’t working with another CEO. That is one reason I loved The Hard Thing About Hard Things so much- vulnerability. On behalf of all CEOs, thank you @bhorowitz).
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17/ Being visionary and effectively communicating the vision are two very different things. It doesn’t work to be the former without the latter. The latter requires repetition. A lot of repetition.
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14/ I need 8 hours of sleep. Maybe I'm weird. But when I started as a CEO I wish more CEOs had publicly said that's ok. The lore of CEOs plowing through with 4 hours of sleep is all you hear.
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I think the average very-successful person that I’ve met has failed far more than the average less-successful person that I’ve met. Often they have the courage, persistence, and ability to try. I recognize this courage often comes with a safety net, but not always.
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4/ I feel all consumed. All the time. It's hard for me to feel present in non-work conversations. On my Friday date night with my wife, I often struggle to focus on us- my mind slips to work. I hate that. I’m embarrassed to admit it. I actively work on it. But I feel all consumed.
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Cultural challenges for CEOs during COVID19. At least challenges for me. 1/ I’ve hesitated to share much through this crisis about the impact it is having on me/us. The health & economic impacts are far more important than startup culture.
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1/ I recently learned a way of framing trust – I don’t know who originally created this equation but I learned separately from @jorgestubbs and LifeLabs. Trust = Credibility x Reliability x Vulnerability. Let’s talk about components of equation and I’ll explain why I love it.
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5/ I feel incredibly lonely. As CEO it’s hard to fully open up about my company and it’s hard to find other CEOs who are willing to be vulnerable and talk honestly about the hard things. The “we’re crushing it” CEO just makes me close down more.
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Buying Optionality. 1/ Over the past year I’ve had a meaningful increase in the # of conversations with new college or MBA grads, or those thinking of going to graduate school. Almost all center around “what should I do?” or “is XXX the right first step if I want to do YYYY”.
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10/ …. And took me 3.5 yrs to find this (which I love)
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1/ Was at a dinner recently with five VCs. All great folks, smart, thoughtful investors. We got to talking about Halo Top and what drove its growth.
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16/ Vision > I didn’t communicate our vision often enough. I still don’t. Whenever we go 60+ days without a vision talk, we begin to fray at the edges. Our vision is here:
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16/ I have reason to believe that innovation will meet this demand. As that happens we will see an explosion of action in the long-tail. More investment, M&A, emerging CPG capturing more shelf space, etc. Prediction: The next 10 yrs are the Golden Age of CPG.
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3/ About 65 VCs passed on us in our Seed Round and about 55 I should have never pitched. Best to research investment history (and current interests via Twitter, blogs, etc) before a pitch meeting - if you don’t have a thesis on why it’s a fit, they certainly won’t.
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3/ I feel the soul crushing stress and pressure of being a venture backed CEO. In the worst moments – missing a goal, letting a team member go, pivoting - it is almost unbearable. In best moments -just closed round, hired someone amazing, hit big goal- I feel pressure about next.
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6/ It was a year and a half before I learned to get an intro to a VC from another CEO. That led to @usv - our Series A. CEO intro beats the lawyer intro - every time.
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25/ A few CEOs recommended for years that I try Transcendental Meditation. I waited 2.5 yrs since starting @CircleUp to try- and haven’t stopped since. It helps calm the mind in an amazing way.
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21/ To open this dialogue, we need to be willing to talk about it. If this made you feel something - better, more connected, more understood, etc. Or if you just feel some of the same feelings, I would love to hear from you and I think others would too. Share your feelings.
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15/ It took me 2 years to write our mission down. I thought I knew what it was so I didn’t bother. Big mistake. A mission is your North Star. Ours is “To help entrepreneurs thrive by giving them the capital and resources they need.”.
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8/ Big-CPG is terrified-as several large CPGs have told me: “If I try to start this co. and it flops, I get fired. If it takes off in a few years, the next person gets credit. Instead I ask corp dev to buy it. If we’re wrong, I don’t get fired.” (real quote from Fortune 200 co).
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2/ Fundraising > Got an introduction to @sequoia from a corporate lawyer. It was the first VC meeting of my life. It lasted 14 minutes. Never get an introduction from a lawyer (neg signal to VC). Never make Sequoia your first VC mtg. Both will make you look like a clown.
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22/ Far too many times I said someone else could make the decision, then I was upset with the outcome. A good CEO needs to learn how to let go.
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6/ I feel tired- mentally and physically – constantly. I sleep less well than I ever have in my life- and almost never am able to catch up on sleep. Not because I’m so busy, but because my mind races and refuses to rest. This has been my reality for 6 years.
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1/ My goal here is to share some difficult experiences I’ve had with boards. Not because I have the answers- there may not have been any.
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VC: "Yeah that's just a really hard category. Super competitive.". [Me thinking: Top notch analysis. Not lazy thinking at all. I bet you also complain that a new category isn't big enough yet.]. Me out loud: "Do you see a lot of large, growing categories that aren't competitive?".
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I find these things equally disgusting:. a) smoking.b) VCs checking their phones during meetings.c) CEOs saying “we’re crushing it”.
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21/ Sometimes meetings are more effective when the CEO isn’t in the room. I still grapple with that.
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9/ So many people told me to focus even after I thought we were focused. They were always right.
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8/ I feel worried that I don’t know what to do. Experts call this Imposter Syndrome. Some of the best leaders I’ve ever seen still have it deep down inside. @bhorowitz THTAHT Chapter 7: How to Lead Even When You Don't Know Where You are Going. (Book I most identify with). .
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Hey @TimDraper honestly the lack of displayed empathy for what your entrepreneurs and LPs are going through right now is offensive. Granted I cant see full email but this is a heck of a way to start. Btw- if you think I'm wrong, consider this: One of your LPs leaked it. 👎.
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1/ I’ve said a few times that I think @Instacart will win in grocery delivery. They will beat @Amazon. It isn’t a popular view, and there aren’t a lot of folks that bet against any part of the Amazon machine.
@ryan_caldbeck Why do you believe that Instacart will beat Amazon?.
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1/Something I have struggled with for years as a CEO. I pride myself in being responsive. This means responding to emails and doing it in a timely manner. It signals I value the emailer. It helps unlock things for others.
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4/ Seeing a huge trend in tech over the past 2-3 years of founders getting profile pieces for themselves to build their personal brand names. Often disconnected with the brand of the company. Basically just a hedge for them for their next job.
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1/ One of the more helpful frameworks I’ve seen as an operator and investor was taught to me by one of our advisors a few yrs ago. When there is a problem, try diagnosing from the top down:. Mission.Vision.Strategy.Culture.People.Tactics.Product.Distribution.Sales.Marketing.
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23/ Mental Health > Get a management coach. I wish I had gotten one sooner and stuck with it. I just started going again and I am reminded how amazing it is.
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Heard from a top beauty founder: “Interesting that VCs say they ‘don’t understand beauty’ and have to ask their wives, but they have no problem on becoming 'experts' on drones….and they had no trouble ramping up quickly on Hims.".
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2/ The arrogance in VC - especially from the smaller funds- is kind of crazy to me. And offensive. AuM = Assets under Management (size of fund)
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3/ At the same time, large brands are spending almost nothing on R&D. They don’t have a pipeline of innovation. They have 50-100 years of R&D-less cultures.
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8/ "Oh do other people like you? Then I like you too." - Says about 95% of tech VCs.
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1/ Over the last 9-12 months I’ve noticed a somewhat fascinating trend in my conversations with successful consumer tech investors: . Many are out on DTC only brands.
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41/ Will some view this as weak? Maybe. Probably. But I’m sharing it here regardless so that other founders going through their own myriad challenges might hopefully feel less alone.
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14/ Didn’t consult with anyone before ordering 60+ puffy jackets suitable for the arctic that look ridiculous in San Francisco. We still have extras of those jackets. Oh and our mission is stitched to the inside. We still have some left if you want one.
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2/ People may make up stories about my intentions. Call me weak, brave, etc. Mental health is a vital topic that doesn’t get enough attention- esp amongst leaders. This isn’t a sign that I’m burnt out or that CircleUp is in a rough spot. Far from it. It’s me sharing how I feel:.
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"Wont Big Company X just copy this?" might be the most overrated concern in the history of evaluating startups. Strategics tend to react too late - and after the startup has obviously been successful. Attempts are typically ineffective. FB Stories -> SNAP a rare exception.
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1/ Had a fun dinner w/ CEO of a large US grocery chain last night. We got into a 3 hour discussion about the future of grocery in the US. Here were some takeaways.
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1/ I’m going to bring some heat in this TweetStorm and talk about the boards of some public CPG companies. Holy what? You’re naming names? Yes. Yes I am. Unfortunately I can’t tag them because most aren’t on Twitter.
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4/ I printed out decks for our first few investor meetings in 2012. No entrepreneur in Silicon Valley history has raised money from an investor after showing up with a printed deck. I was not the first. I cringe thinking about those mtgs.
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19/ I learned this the hard way after lots and lots of failure. Keep your deck tight. 10-15 pgs.
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I deeply hate @ABCSharkTank for a bunch of reasons- but one is the clown music the producers play in the background when an entrepreneur has an idea that won't get traction. So disrespectful to those founders and their journey.
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10/ As your team gets larger people realize they can't know everything. They will complain until collectively you figure out how to spread knowledge effectively.
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19/ I’m also writing this to hopefully create empathy. Empathy amongst entrepreneurs, teammates they build with every day, VCs that fund them, friends and families that support their journey. I’m hopeful that this empathy will create safe spaces for others to share their journey.
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20/ It's ok to be scared. It's ok to be worried. It's ok to be tired. If we can talk about it, and build bridges to support & encourage each other the system overall will be more inclusive, more reassuring, more open. Everyone is on their own journey - now you know part of mine.
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I have learned that 10,000 hours of playing basketball has -at best- a negative correlation to my effectiveness in coaching basketball to 5 yrs olds. All of my dreams of passing on insights are dashed when one of the players wont stop hugging my leg and 3 just want snacks.
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7/ A huge portion of the dinners and networking events in Silicon Valley have nothing to do with helping you run your company. Skip 'em.
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3/ If the VC is into you they will email. right away. Meaning RIGHT away.
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11/ I feel jealous almost every time I talk to another entrepreneur. They always seem to be better than me or us at something, anything. Shows like Silicon Valley are not fun for me - my mind just spins about things we could be doing better. Or reminds me of painful failures.
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So important that a team member at a startup can ride the emotional ups and down. And so so hard to screen for it. Have you found any good ways in the interview to identify that ability to ride the roller coaster? (other than prior startup experience of the candidate).
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7/ I feel scared. The fear has increased with time and I had thought it would decrease. Fear that I will disappoint people, fear that our effort will be wasted, scared that new team members won’t want to join or that our best will leave.
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A great thing about tech ecosystem is amount of content that gets created to help others. This from @andrewchen is 👌. In CPG this would sell for $5k a pop and be 10% as good. Andrew gives this away for free and makes everyone better. Thank you.
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I’m a big fan of hiring when we find a candidate we like instead of running a “process”. I think that waiting to talk to multiple candidates leads to a culture of always looking for a shinier object – and a worse end result. The quest for perfect can destroy really damn good.
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1/ I’ve said before that PASSION is what I look for the most in new teammates or investors. I believe - based on no scientific research at all- that passion is the most important ingredient for success. It is my only interview question (“what are you passionate about and why”).
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12/ I feel all these things every day and I know many other CEOs do too - wherever they live, whatever type of co/org/team they lead. Fear, self-doubt, and fatigue…. But it’s really really hard to say it out loud. Especially in Silicon Valley where there is So. Much. Posturing.
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I wish a site existed where Product Managers could anonymously evaluate/explain their decisions in post-mortems. To hear what @Twitter thought through with this redesign would be fascinating.
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1/ The concept of a Holding Company in CPG to be the @ProcterGamble for the 21st Century is the worst kept secret idea over the past 24 months. Kind of a lot of people are trying to build this.
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18/ The companies talking about perks are the ones that have to talk about perks.
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I like watching VCs tweet about how startup CEOs got used to an easy fundraising environment and that led them to hire too much over last 5-10 yrs. as if many of those same VCs weren't pressuring their portfolio co's to raise more than they needed and over hire along the way
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1/ I’ve been trying to convince teammates to create more content externally. Blogs, Tweets, MySpace ramblings, Homing Pigeon messages. Here are my arguments for why they should.
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4/ Big-CPG spends too much on mtkg. So you have stale incumbents pumping $ into marketing the same products they’ve sold for 50 years. Btw- kudos to @KITKAT for evolving their tagline from "Have a break" (1960's) to "Gimme a Break" (now). Impressive.
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Getting fired. 1/ I interviewed someone recently and I asked “have you ever gotten fired” (Huge disclosure I have no idea if this is kosher to ask- I went rogue). I was incredibly impressed by her answer and it helped clarify my thinking of getting fired.
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1/ I joined @DuneAnalytics as COO in Oct 2022. This is my first full time role since stepping down from CircleUp in June 2021. Here is why I am excited to have joined.
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1/ I think @faire_wholesale is (still) hugely undervalued at $12b. They’ve identified an incredibly valuable wedge to absolutely massive markets and are just getting started. [I’m not an investor, I just admire how they are solving big problems].
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