The Two Mindsets That Can KILL Your Startup

Dalton Caldwell and Michael Seibel discuss the qualities that make a founder overly optimistic or far too pessimistic about their startup. Where is the right middle ground?
Apply to Y Combinator: yc.link/DandM-apply
Work at a Startup: yc.link/DandM-jobs
Chapters (Powered by bit.ly/chapterme-yc) -
00:00 - Introduction
00:30 - Stereotypes
03:09 - The Two Leaders
05:45 - Pessimistic mistakes
06:28 - Expectation setting
07:14 - Faulty feedback
08:24 - Demo day goals
09:20 - Energy drain
11:22 - Magical thinking
14:23 - Founder mistakes
16:03 - Product mistakes
17:43 - Magical investors
18:41 - Hiring optimism
19:57 - Doing what's cool
21:46 - Cognitive dissonance
#startups #entrepreneur #tech

[@ycombinator]

How do you develop a realistic view of your startup?

[@singh.deepak]

If we exactly know whats working out and what's not.

[@arjungupta-inventor-iaq]

Unplug and try to watch from a distance. Have a few trusted friends who know some about your domain and ask them the right questions. Not questions like will I succeed.

[@cryptonative]

@@singh.deepak If you have customers paying is working. If people are telling their friends or collegues is also working.

[@entertainmentyoutube3606]

the more solid the idea and execution are, the fewer problems you will encounter, nomad list was profitable from the beginning

[@chaitanyavaidya7783]

Pick a growth metric and stick to it

[@JasonGoodison]

Didn't realize the "100 emails doesnt convert to 100 leads" problem was common. The second you said it I realized I fit solidly into that category

[@chapterme]

Chapters (Powered by ChapterMe) - 00:00 - Introduction 00:30 - Stereotypes 03:09 - The Two Leaders - Who would you want to work for? 05:45 - Pessimistic mistakes 06:28 - Expectation setting 07:14 - Faulty feedback 08:24 - Demo day goals 09:20 - Energy drain - Gave up too early 11:22 - Magical thinking - Optimism is hard 14:23 - Startups - Founder mistakes 16:03 - Product mistakes 17:43 - Magical investors 18:41 - Hiring optimism 19:57 - Doing what's cool 21:46 - Having balance - Cognitive dissonance

[@kevinopati5784]

Really hard to find a wiser duo in the startup world. Thank you for everything.

[@BrendanDell]

Brilliant topic of discussion, it's the yin and yang of both being grounded in the task ahead but believing that your idea and business have a future that is valuable and worthy of your time and energy. Seibel's comment on the purpose of goals not necessarily being to nail the goal but giving you the drive and the valuable lessons it teaches you along the way- couldn't have said it better. Definitely going to be sharing this with my community. Thank you!

[@GauravSharma1]

What a fantastic episode. Can so much relate to this. Holding multiple realities in the head and still being an optimist is a super-power.

[@bowlerkid]

Guys, thanks for putting this up! I it’s really helps battle the magical, thinking, as well as the overreliance on pessimism to wish you towards reality.

[@derek-yap]

Yup, I feel like a lot of CEOs I've worked for are afraid of not being optimistic when addressing the company at an all-hands or something. To me that always seemed a little disingenuous. Like we're not kids, we know layoffs aren't good, why are you telling us this is actually a good thing. In fact most employees at tech companies are highly intelligent. Just be real.

[@dereklough1815]

It's so exciting to watch my ego be dismantled in realtime. Thanks for the straight-talk.

[@StreamAgency]

This video offended me both as a pessimist and an optimist; Realists always suffer the most.

[@mahdi5796]

Insightful as always. Please keep the wonderful serie of conversations

[@oldewolf5275]

Great stuff. We (Olde Wolf) applied for this winter batch because of these videos (I hadn't heard of Y Combinator beforehand. I know, shame on me). Your buddy, Justin, also seems like he balances helpfulness with personability as well! Cheers, guys.

[@yafiwala]

Growing a Start-up is like Motherhood where you got both emotions daily what if my child(start-up) won't be able to make it and my child(start-up) is going to survive because I'll nurture it. But, it's a beautiful experience just like Motherhood.

[@georgeopiyo6004]

Thanks guys you are amazing ! You are impacting so many lives than you can even imagine . Thanks long life and health to you two

[@juanmdq]

Wow! I'm in a stage where this video is just what I needed! Thank u guys!

[@randy4ii411]

Love your talks guys. I good “startup compass” is very useful when you feel a bit like you are in a possibility wilderness.

[@aaronb2551]

I like the "cognitive dissonance" part of it. Thanks for enunciating that.

[@catwithacowboyhat]

I love this series! Keep it up please!

[@ShoaibMahmudOfficial]

Be optimistic, but don't be too magically optimistic! It feels great to learn directly from you.

[@MikeWilliamsYoroomie]

Such a great conversation and keep these coming!

[@whatisrokosbasilisk80]

Wow, this was insanely valuable - I never suspected that I, a perpetual cynic, would actually be too optimistic!

[@rossnwilliams]

I have a subwoofer and this video has a lot of bursts of sound around 30Hz to 40Hz. I suggest you add a low-cut filter.

[@zetendra]

thank you, it's such a wonderful episode

[@mjmikaelson]

Thank you for sharing this episode gentlemen! I really appreciate it So much! 😊

[@george_davituri]

quote: ''you need to get in before everyone thinks it's cool'', brilliant advice. great talk

[@AnomalyHQ]

These videos are great, thanks for recording and sharing these

[@josephekpaha]

Seems you're some kinda startup Knowledge gods. Everything said well enough and perfect 👌

[@jimifash]

Cognitive dissonance! Be rooted in reality! Priceless gems 👌

[@chargreen1742]

This was so encouraging to go forward and apply to YC

[@anirudhm]

Thanks for doing this!

[@yaelfelicia5820]

Literally the best videos on the Tube for founders - you guys rock. 💪🏽

[@entertainmentyoutube3606]

9 of 10 businesses fail so you have to be a little crazy to be an entrepreneur and keep trying after every punch but the reward is so fking good that is worth it

[@HarisKhan-bh6uj]

great episode !!

[@nidhi2581]

You guys are so goood!!! Looking forward to your next video.

[@israeldavid3553]

Having a vision for your startup, working on the small and big issues. Always being focused and be willing to start small whilst thinking big.

[@adarshalt1161]

Balance is key.

[@rockbaby411]

Wild they used a chatbot as an example and said "it was over" - this video came out two months before ChatGPT - shows that even these guys with past success can't predict the future

[@gogemusicimprov4421]

LOL 1:34 Dalton said Eeyore, but I heard Eol and was impressed he read and referenced silmarillion.

[@curiouscarbon1181]

Really like the moving topics format of your videos! Does someone edit the videos and add them manually or do you use some software to generate them?

[@ycombinator]

Zach, the video producer here. These are edited in Adobe Premiere. We custom made an Essential Graphics package that allow us to easily duplicate and edit these lists for each video.

[@sivashankarimurugesan7120]

Thank you.guys...its very useful😊

[@serkanuz]

I think I am not too optimistic about every subject. But, I am too optimistic about hiring. Being too optimistic, maybe doesn't mean you are too optimistic about every subject. Amazing video, thanks for clarifying all these subjects.

[@LazizbekYusupov92]

Manda ham shunday odat bor. Bir marta ko’plab odamlarni sihga olishga mas’ul qilindim. Oxiri ko’pchiligi ishni eplay olmay, orqamga pichoq urdi. Bu darsdan keyin odam tanlashda ehtiyotroq bo’ldim.

[@AlexCookaacook]

Fantastic, thanks!

[@singh.deepak]

Great Conversation. 🙂✌👍

[@lboogy1708]

Best of both worlds, every entrepreneurs should learn how to wear both hats from day 1 and welcome the reality to judge

[@arjungupta-inventor-iaq]

Being rational and not far on either sides is the goal! Good to know you guys see pessimist founders often. I always thought founders are all stars in the eyes always optimistic

[@michaelmcwhirter]

This is one of the greatest videos you guys made!

[@jaredbeckwith]

Have a right balance of pessimism and optimism!

[@christopherjskinner]

Results driven systems thinker startup mindset of leadership is what gets you to success.

[@engr-lynx]

Great episode! But I dislike the resolution that one needs cognitive dissonance to be in a balance. It suggests that pessimism-optimism is binary. When in fact, it's a spectrum. Furthermore, you can be at different points of that spectrum for various situations. In fact, the ability to apply the correct amount means you're a realist. They say that a pessimist sees the glass as half empty while the optimist sees it as half full. But I'd add to that that the realist just sees a glass that needs to be filled or emptied depending on the desired outcome.

[@CaliforniaRussianRiverBees]

Great Information 🕹💻 thank you Gentlemen🎙I tell people 🏆🏆The law of averages will kick in if you knock on enough doors. You guys are great telling the truth 🫵🏼🍾🎉💵💵💰💰

[@justingirard7476]

The wider the psychological range, the more analytical concepts (optimistic and pessimistic) a person can use to frame reality. This is a muscle, and I have a process to enter both states, and it is a critical import toolset

[@andgo]

What would be better?, to think of yourself as an optimistic (but not overly optimistic) person or as an objective (or realistic) person?

[@shermanmcdermott4211]

what advice would you give to a startup in an extremely technical space? a B2B product that is not intended for the mass market? is it a good idea to only talk about the benifet, and gloss over the technical detail that makes it realistic, or is it a better idea to 'dumb it down' to be easily digestible?

[@James-mk8jp]

Founders have no choice but to be optimistic.

[@benditovicentecosta1710]

Summing up what I did get: Aim to the stars, and get to the moon

[@alexf7414]

A pessimistic sees a u-turn at every intersection, an optimistic runs the red light most of the time.

[@AmarAmte6644]

The planets are aligning haha. Rainbows and Ponies omg haha

[@waxcomb]

Is Michael on the blood transfusion program Peter Theil is on. Skin is so luminous

[@Gadekko]

He got himself a blood-boy

[@entalpa]

hahaha

[@diegoallcore]

1:42 my dog stepped on a bee?

[@juanmdq]

Hahahhahah

[@quasa0]

Dalton feels a bit anxious in this video. And all of us (I'm not the only one right?) do frequently. Could you share your advice on how do you deal with anxiety and bad mood / etc periods that are constantly coming up? I did see the founders habits video with some advice on this, but I feel like you have more ideas to share, especially from your experience with founders

[@Okeh_Emmanuel]

...and the ultimate Reality is, users and payimg customers

[@briank624]

Magical thinking comes from business school and media. No one starts with the answer. We stumble through. 20/20 narrative is great

[@woodsdog22]

Jump into and check the OARBED mindset. A lot of the things discussed here are to do with the wrong mindset. But if you need something to live by and that is easy and actionable, check it out. It’s powerful and the team can lean into it really easily.

[@chumaggotscaesar]

what about pessimism of strength?

[@jungtarcph]

This made me laugh.... Remember Alan Greenspan as head of FED in 1999 when he just thought there was some magical new economy 🤣🤣😂😂😊😊🙌🙌

[@sebastianlueders6399]

Somehow I think I jump from pessimist to optimist on a daily basis... Startup life is way more volatile than advertised

[@juanmdq]

Totally!

[@juanmdq]

What sector are you in?

[@angcil88]

Used to be very optimistic, now I'm pretty much a skeptic.. slightly pessimistic sometimes lmao

[@kdietz65]

On the pessimistic thinking side, this is exactly why I don't like Lean Startup. It sets too high of expectations on the early feedback cycle and makes you vulnerable to overly pessimistic thinking. If prospects don't immediately hit an aha moment, if they don't throw rose petals at your feet right away, then according to Lean Startup you're supposed to do what? Give up? Or pivot too early? It just doesn't make any sense. It encourages you to let the tail wag the dog and make decisions that are too big based on too little early feedback. I've definitely been waved off of very good ideas because the people I talked to didn't get it right away. Getting very early feedback that is also accurate is quite difficult to do in my experience. You're better off following your intuitions and doing general market research on the Internet vs. talking directly to people. You can talk to people if you want, just don't make any actual decisions based on what they say.

[@juanmdq]

Balance is the key here...there are. No manuals ..

[@angiekarasek]

What about optimistic people who are over thinkers?

[@thetrends5670]

🖤

[@keerthivasanb7931]

7:16 21:50

[@dominicwood3750]

How come SV tends to only fund book smart people? The business world is full of people who aren’t academics.

[@d7ffab979]

16:45

[@rishabhs.292]

I am overly pessimistic, what should I do.

[@juanmdq]

Set realistic expectations ;)

[@d7ffab979]

11:30

[@gabormilisics6853]

Good content but please say "like" a bit less frequently

[@entalpa]

There are people who don't need Michael to build a good startup and there are people who need Michael the build a good startup and there are people that even with help of Michael can't build a good startup. Where do you fit?

[@knyansa1569]

I am ambimistic

[@amirMahmed]

I Am Very Optemistic Guy

[@danielbeltran5020]

what is all those cringe laughs guys haha, other than that, very good talk!!

[@BrianMartensOfficial]

Heroin vs. Cocaine.

[@leonsvideos]

that's why I go for the balance in the middle: Crack

[@cryptonative]

Who’s eeyore?

[@rickhmason]

A character from the Winnie the Pooh book series. He is generally described as pessimistic and depressed all the time.

[@cryptonative]

@@rickhmason I see. In my language they name him Gary for some reason!

[@abdulazizalanazi5822]

When I first saw the thumbnail I thought Michael was announcing being gay 💀

[@bernardmomanyinyagaka1051]

"Oh we have this big problem in the company, and we think hiring a marketing person or sales person will come and solve the biggest problem in the company that we ourselves haven't figured how to solve" This is hilarious, talking to us😂😂

[@MrNewAmerican]

Please don’t giggle. You’re not a teenage girl and this is not a teenage sitcom.

[@yamilletrivas8041]

Your definition of magical thinking should be called "delusional thinking" because magical thinking is definitely not that lol. (Although I want to see Michael at the airport and get funded etc etc lol!

[@chumaggotscaesar]

I just wanna die a victorious death

[@ollydix]

I think you got confused between pessimistic and depressed 😂

[@alok1]

So insighful

[@allenmandikutse]

Tarpit ideas 😑

[@mcano3375]

Jesus-Christ est le Fils de Dieu. Fils de l'Homme, et l'image de Dieu. il sauve ceux qui croit en lui. lisez la bible surtout le nouveau testament

[@rahulnath1912]

dalton what's your address? I gotta send you a mic, dude

[@CaliforniaRussianRiverBees]

Great Information. Build good relationships to execute and hopefully the Ideas are good, put testing is better. Love what you do💼 thank you🏌