How to Conquer Bad Days at Your Startup

1. 0:00 – 1:01

   Why founders remember the near-death moments more than the wins

   1. MSMichael Seibel0:00

      I often get asked the question, like, "Tell me the story of, like, the day that, like, Twitch sold." And I'm like, "Yeah, that was fine. I have some memories of that, but tell me the story of the five times Twitch died, almost died. I remember those, like, minute by minute." And to me, those are the moments where we had to grow.

   2. SPSpeaker0:20

      Yeah.

   3. MSMichael Seibel0:20

      And so I would argue that, like, I'm not saying you want bad days. I'm saying bad days teach you a lot more than good days do. [upbeat music] This is Dalton + Michael, and today we're gonna talk about bad days when you're doing your startup. I have not experienced any bad days, but I've heard-

   4. SPSpeaker0:40

      [laughs]

   5. MSMichael Seibel0:40

      ... you had a couple bad days during your startup-

   6. SPSpeaker0:43

      Oh, man

   7. MSMichael Seibel0:43

      ... uh, journey.

   8. SPSpeaker0:44

      I've had some bad days, Michael.

   9. MSMichael Seibel0:45

      [laughs]

   10. SPSpeaker0:45

       I've had some bad days.

   11. MSMichael Seibel0:46

       So for founders watching this, um, let's assume the kind of setup here is that they're watching this video, and they're saying, "Man, I just got punched in the face today." So tell us a story. Tell us some thoughts.

2. 1:01 – 2:27

   Startups expose you to raw, unfiltered reality (unlike big-company “filters”)

   1. SPSpeaker1:01

      I think where I would start is it's awesome to be a startup founder, and I feel like most people-

   2. MSMichael Seibel1:10

      Mm-hmm

   3. SPSpeaker1:10

      ... in their job, there's these filters where you don't get-

   4. MSMichael Seibel1:14

      Yes

   5. SPSpeaker1:14

      ... exposed to, like, raw reality.

   6. MSMichael Seibel1:16

      No.

   7. SPSpeaker1:16

      Like, if you work inside Google or something, you're in your hermetically sealed pod.

   8. MSMichael Seibel1:21

      No.

   9. SPSpeaker1:21

      And really good things don't really affect you, really bad things. Like, you're just-

   10. MSMichael Seibel1:25

       It's almost designed that way.

   11. SPSpeaker1:26

       Yeah.

   12. MSMichael Seibel1:26

       Yes.

   13. SPSpeaker1:26

       You're inside of the machine.

   14. MSMichael Seibel1:27

       Yes.

   15. SPSpeaker1:28

       And so stuff happening out in the world does not make it to you.

   16. MSMichael Seibel1:31

       You're not trusted for that.

   17. SPSpeaker1:33

       Yeah.

   18. MSMichael Seibel1:34

       [laughs]

   19. SPSpeaker1:34

       But when you're running a startup, you are getting cold, unfiltered reality-

   20. MSMichael Seibel1:40

       Yes

   21. SPSpeaker1:40

       ... which often means really awesome things happen-

   22. MSMichael Seibel1:44

       Mm-hmm

   23. SPSpeaker1:44

       ... and you feel really good.

   24. MSMichael Seibel1:45

       Mm-hmm.

   25. SPSpeaker1:46

       And really not awesome things happen, and you feel really bad. So you might get emails on any given day-

   26. MSMichael Seibel1:52

       Yeah

   27. SPSpeaker1:52

       ... of someone being like, "I hate you. I hate your product."

   28. MSMichael Seibel1:54

       Yep.

   29. SPSpeaker1:55

       "You ruined my life." [laughs]

   30. MSMichael Seibel1:56

       Yep. Maybe that's in the press. [laughs]
3. 2:27 – 3:34

   Being the scout: when something bad happens, it’s your problem

   1. MSMichael Seibel2:27

      No. I think that, um, it's this weird concept of both being a general and being, like, the scout. Like, you're not even on the frontline. You're the scout, right? You're the first person in the line on patrol, like, the first person who's gonna get shot-

   2. SPSpeaker2:44

      Yeah

   3. MSMichael Seibel2:44

      ... when there's an ambush. [laughs]

   4. SPSpeaker2:45

      When something bad happens, it's your problem.

   5. MSMichael Seibel2:47

      Exactly. [laughs]

   6. SPSpeaker2:49

      Right?

   7. MSMichael Seibel2:49

      Um, but on the flip side, when you talk to founders, I think, who've experienced, you know, built great startups, I think one of the counterintuitive things is how much they look back on the bad days with fondness. And I think that's like, I often get asked the question, like, "Tell me the story of, like, the day that, like, Twitch sold." And I'm like, "Yeah, that was fine. I have some memories of that, but tell me the story of the five times Twitch died, almost died. I remember those, like, minute by minute." And to me, those are the moments where we had to grow.

   8. SPSpeaker3:26

      Yeah.

   9. MSMichael Seibel3:27

      And so I would argue that, like, I'm not saying you want bad days. I'm saying bad days teach you a lot more than good days do.

4. 3:34 – 3:59

   Normalizing the urge to quit—and why learning to cope is mandatory

   1. SPSpeaker3:34

      And you have to get good at dealing with them-

   2. MSMichael Seibel3:39

      Yes

   3. SPSpeaker3:39

      ... or you're not gonna make it. [laughs]

   4. MSMichael Seibel3:41

      [laughs]

   5. SPSpeaker3:41

      Which is why we're making this video.

   6. MSMichael Seibel3:43

      No.

   7. SPSpeaker3:43

      Which is to, to, to be like, yeah, you're not... You're normal. You're not unusual if you feel like you have days that make you wanna quit your startup and give up. Like, yep, that's pretty much part of it. [laughs]

   8. MSMichael Seibel3:54

      [laughs]

   9. SPSpeaker3:55

      Yeah, that's-

   10. MSMichael Seibel3:55

       Check. [laughs]

   11. SPSpeaker3:56

       [laughs] That's, uh, that's part of it.

   12. MSMichael Seibel3:58

       Yes, that's, that's part of it.

5. 3:59 – 4:33

   Technique: put the worst-case scenario on the table (“so what?”)

   1. SPSpeaker3:59

      And so, you know, what, what, my first technique I would use when this would come up in office hours would be like, "Okay, well, let's talk about what if the worst thing happens?"

   2. MSMichael Seibel4:09

      Yeah.

   3. SPSpeaker4:09

      "Let's just talk about it."

   4. MSMichael Seibel4:10

      Yeah.

   5. SPSpeaker4:10

      "Let's just put it on the table. Like, this, this thing that you're afraid of or this really bad thing that happens."

   6. MSMichael Seibel4:15

      Yes.

   7. SPSpeaker4:15

      "So what?"

   8. MSMichael Seibel4:16

      Yes.

   9. SPSpeaker4:17

      Right?

   10. MSMichael Seibel4:17

       I love that technique. I, I often call it, like, "Hey, tell me what the boogeyman is," and the like, "Let's open the door and look at the boogeyman."

   11. SPSpeaker4:25

       Yeah.

   12. MSMichael Seibel4:25

       'Cause usually the thing you're afraid of isn't as scary as you might think if you actually examine it closely.

6. 4:33 – 5:14

   Example: Demo Day fundraising fear—what if you raise nothing?

   1. SPSpeaker4:33

      I mean, the most common one I got-

   2. MSMichael Seibel4:34

      Yeah

   3. SPSpeaker4:34

      ... and I'd love to hear your example, but it was a company during the YC batch being like freaking out about demo day fundraising.

   4. MSMichael Seibel4:42

      Yeah.

   5. SPSpeaker4:42

      And I'd be like, "Okay, let's talk about it. Let's say it goes bad."

   6. MSMichael Seibel4:47

      You raise

   7. SPSpeaker4:49

      You raise no money.

   8. MSMichael Seibel4:50

      Yeah.

   9. SPSpeaker4:51

      How bad would that be really?

   10. MSMichael Seibel4:54

       And then they're like, "Well, actually, we c- you know, at our current burn-" [laughs]

   11. SPSpeaker4:57

       "We have three years of runway," you know? And I'm like, "Okay."

   12. MSMichael Seibel5:00

       Yeah.

   13. SPSpeaker5:00

       And so-

   14. MSMichael Seibel5:01

       So you don't die?

   15. SPSpeaker5:02

       So, okay, so what? Like, well, let's talk about it.

   16. MSMichael Seibel5:05

       Yeah.

   17. SPSpeaker5:05

       Let's just say it happens.

   18. MSMichael Seibel5:06

       Yeah.

   19. SPSpeaker5:06

       Are you gonna be okay? And they'd be like, "Yeah."

   20. MSMichael Seibel5:09

       Will your customers run away? Are customers watching your fundraising progress on demo day? [laughs]

   21. SPSpeaker5:13

       Yeah.

7. 5:14 – 6:19

   Example: the bandwidth bill bigger than the bank account—bad days force innovation

   1. MSMichael Seibel5:14

      And they're like, "No." Yeah, so no, I, I, I love that one. I think another one that comes up in my mind is on terms of, like, the worst thing that could happen. It reminds me of a story in my startup where we got a bill after the first month of Twitch. It was Justin.tv back then. We got a, we got a bandwidth bill from our CDN that was bigger than the amount of money in our bank account.

   2. SPSpeaker5:35

      [laughs]

   3. MSMichael Seibel5:36

      And, like, I love those moments because they force you to innovate, right?

   4. SPSpeaker5:45

      [laughs]

   5. MSMichael Seibel5:45

      Like, you're s- you're supposed to be innovating all the time, but you're kind of in a comfort zone, and now you're just like-

   6. SPSpeaker5:49

      That's a really nice way to put it, Michael

   7. MSMichael Seibel5:51

      ... right? And you're just like, "Well, okay."

   8. SPSpeaker5:52

      Forced to innovate.

   9. MSMichael Seibel5:53

      "Let's say I paid this bill." We would be bankrupt immediately plus, right? [laughs]

   10. SPSpeaker5:59

       [laughs]

   11. MSMichael Seibel5:59

       Like, right, plus. Like, we don't, we, we actually don't have enough money to pay, so I guess we'd, like, what, take out a credit card, whatever. So, like, I can't pay the bill. So what do we do now? And to me, I think those moments are so interesting and exciting because, I don't know, my nickname in college was Same-Day Cybo. I liked to do my assignments the same day they were due.

   12. SPSpeaker6:19

       That's good.

8. 6:19 – 7:03

   Bad days become legendary days—and create veterans inside the company

   1. MSMichael Seibel6:19

      And in this weird way, startups kind of encourage that, right? Like, the punch comes from out of the blue, and then what's the plan? What are you gonna do? And there's no boss to talk to. There's no what is the organizational yet. It's like, no. Like, the Germans are coming. They're... Like, you can see them. What are we gonna do? And I think that for the right kind of people, those bad days suddenly become their, like, legendary days.

   2. SPSpeaker6:47

      Yeah.

   3. MSMichael Seibel6:48

      Right? And, like, inside of a company, once you start surviving bad days, like, you, you, you almost become a veteran. You're like, "Oh," like-

   4. SPSpeaker6:55

      This is the job. [laughs]

   5. MSMichael Seibel6:56

      Yeah. And, like, we survived the last five punches to the face, so, like, the next one, no problem.

9. 7:03 – 8:20

   You don’t outgrow bad days: high-profile crises still happen at the top

   1. SPSpeaker7:03

      And I think that sometimes you wanna believe that someday you will outgrow the bad days, and you'll be so successful that you will not have bad days anymore. And so to put this into perspective-

   2. MSMichael Seibel7:15

      [laughs]

   3. SPSpeaker7:16

      ... I think it's easy if you're watching this video to see someone like Sam Altman as, like, a fictional literary char- you know, he's like a character from fiction, not a real guy.

   4. MSMichael Seibel7:25

      Yes.

   5. SPSpeaker7:25

      He's a real guy. We know him.

   6. MSMichael Seibel7:26

      Yes. Yes, yes, yes.

   7. SPSpeaker7:27

      We know him really well. Imagine having a bad day that is literally international news that you got fired-

   8. MSMichael Seibel7:33

      Mm-hmm

   9. SPSpeaker7:33

      ... and lost control of your company and got stabbed in the back. That's a pretty bad day.

   10. MSMichael Seibel7:38

       Yep.

   11. SPSpeaker7:38

       Like, I, I can only imagine what that must have felt like.

   12. MSMichael Seibel7:41

       Mm-hmm.

   13. SPSpeaker7:41

       And what's fascinating, A, if you know the guy, and B, if you read what he actually did when that incident happened, he was just like, "Oh, let me do some stuff. Let me make some calls."

   14. MSMichael Seibel7:53

       Work the problem.

   15. SPSpeaker7:54

       Like, he basically-

   16. MSMichael Seibel7:55

       Yeah

   17. SPSpeaker7:55

       ... did not freak out-

   18. MSMichael Seibel7:56

       No

   19. SPSpeaker7:57

       ... as far as I can tell, or he at least was immediately coming up with plan B-

   20. MSMichael Seibel8:02

       Yeah

   21. SPSpeaker8:02

       ... and making calls and parlaying resources-

   22. MSMichael Seibel8:04

       Yep

   23. SPSpeaker8:05

       ... to fix it-

   24. MSMichael Seibel8:06

       Yep

   25. SPSpeaker8:06

       ... instead of-

   26. MSMichael Seibel8:08

       Yeah, do nothing

   27. SPSpeaker8:09

       ... collapsing.

   28. MSMichael Seibel8:10

       Yeah, yeah.

   29. SPSpeaker8:10

       [laughs] Yeah, I think that was a really bad day, and I think all of his prior bad days were probably preparation for that.

   30. MSMichael Seibel8:16

       Yes.
10. 8:20 – 9:01

    Reframing: the goal isn’t to dodge bad days—bad days build armor

    1. MSMichael Seibel8:20

       Well, this brings up a really good point, right? Your goal as a startup founder is not to, like, dodge bad days, and, like, having a bad day doesn't mean you did something wrong. Like, in some counterintuitive way, it's preparing you for the next bad day, and it's like building up your armor. And so, like, you should think of it as that when your company succeeds, you're gonna have so much armor that, like, when the bad days happens, like, you're, you're, you're ready. Like, you're trained, right? It's like you've been to the gym.

    2. SPSpeaker8:50

       And, and you believe you're on a mission-

    3. MSMichael Seibel8:52

       Yes

    4. SPSpeaker8:52

       ... that you believe in.

    5. MSMichael Seibel8:53

       Yes.

    6. SPSpeaker8:53

       Like, again, like, if it, what gets people through these things-

    7. MSMichael Seibel8:55

       Yes

    8. SPSpeaker8:55

       ... it's the belief that it's worth-

    9. MSMichael Seibel8:59

       Yes

    10. SPSpeaker9:00

        ... it's worth doing.

    11. MSMichael Seibel9:01

        Yes.

11. 9:01 – 9:44

    Nobody is immune: criticism can flip, and bad days keep coming

    1. SPSpeaker9:01

       I mean, another example, again, I guess this is OpenAI and Thron, um, competitor, but with Anthropic, think of how funny it is. What was it, 18 months ago?

    2. MSMichael Seibel9:09

       Mm-hmm.

    3. SPSpeaker9:09

       Elon tweeted something like, "They'll never win. They're, like, a four-three." You know, like he said just basically-

    4. MSMichael Seibel9:15

       Yeah

    5. SPSpeaker9:15

       ... "They're l- they're in last place."

    6. MSMichael Seibel9:17

       Yeah.

    7. SPSpeaker9:17

       It's a joke.

    8. MSMichael Seibel9:17

       The richest technologist/person-

    9. SPSpeaker9:20

       Yeah

    10. MSMichael Seibel9:20

        ... on Earth.

    11. SPSpeaker9:20

        And again, I'm arguing they probably saw that tweet.

    12. MSMichael Seibel9:22

        The shitposter story. [laughs]

    13. SPSpeaker9:23

        They probably saw the tweet, and that probably didn't make them feel good.

    14. MSMichael Seibel9:26

        No.

    15. SPSpeaker9:26

        Um, and then, you know, whatever, 12 months later, Elon signs a deal to buy compute from them.

    16. MSMichael Seibel9:31

        Yeah. [laughs]

    17. SPSpeaker9:33

        [laughs] And so again, where I'm going with this is no one is immune from these things, friends.

    18. MSMichael Seibel9:39

        Yeah.

    19. SPSpeaker9:39

        Like, you'll never reach a point where you don't have bad days if you're doing a startup.

12. 9:44 – 10:22

    Expectation-setting: bad days can signal you’re doing real work (and growing)

    1. MSMichael Seibel9:44

       Yeah. [laughs] Well, and by the way, I love this point because I think that so often founders defeat themselves by not having the right expectations. And, like, we're trying to tell you, like, expect bad days.

    2. SPSpeaker9:56

       [laughs]

    3. MSMichael Seibel9:57

       I- in fact, like, I might argue that bad days, in some cases, can be indication that you're actually doing stuff. You know? Like, if you're having no bad days, I'd argue you're-

    4. SPSpeaker10:08

       It probably means you're not growing.

    5. MSMichael Seibel10:09

       Yeah.

    6. SPSpeaker10:09

       Like, like, growth and bad days tend to come in bundles.

    7. MSMichael Seibel10:12

       Yeah, exactly, [laughs] yeah.

    8. SPSpeaker10:13

       Like, the faster you're growing, the more likely wacky stuff starts happening to you.

    9. MSMichael Seibel10:17

       Counterintuitively, the better you're doing, the more bad days you're gonna have. I think that's very counterintuitive.

13. 10:22 – 12:01

    Growth attracts attention—and with it, conflict: imeem scaling story

    1. SPSpeaker10:22

       That, that exactly happened to me as a startup founder-

    2. MSMichael Seibel10:24

       Yes

    3. SPSpeaker10:24

       ... when I was running imeem, is we started growing really fast.

    4. MSMichael Seibel10:29

       Yes.

    5. SPSpeaker10:29

       And as we started signing up 50,000 users a day, 100,000 users a day, things started happening to me.

    6. MSMichael Seibel10:37

       [laughs] Yeah, yeah, yeah.

    7. SPSpeaker10:38

       Like, like, I started getting e- like, we started showing up on people's radars.

    8. MSMichael Seibel10:42

       Yes.

    9. SPSpeaker10:42

       Like, investors' radars-

    10. MSMichael Seibel10:44

        Yes

    11. SPSpeaker10:44

        ... uh, lawyers' radars-

    12. MSMichael Seibel10:46

        Yes

    13. SPSpeaker10:46

        ... the music industry.

    14. MSMichael Seibel10:47

        Yes.

    15. SPSpeaker10:47

        Actually, artists.

    16. MSMichael Seibel10:48

        Yes.

    17. SPSpeaker10:49

        So, so all these people-

    18. MSMichael Seibel10:51

        Inbound. [laughs]

    19. SPSpeaker10:51

        Like, all this stuff started happening to me as a consequence of my startup growing.

    20. MSMichael Seibel10:55

        Yes.

    21. SPSpeaker10:56

        And some of it was good, but a lot of it was, like, people were really mad at me.

    22. MSMichael Seibel10:59

        Yep.

    23. SPSpeaker10:59

        And it was weird that somehow making a very successful startup caused some percentage of people to get really mad at me, but it totally happened.

    24. MSMichael Seibel11:07

        Yes.

    25. SPSpeaker11:07

        That was my experience. [laughs]

    26. MSMichael Seibel11:08

        And that should be your expectation. That should be your ex-

    27. SPSpeaker11:10

        [laughs]

    28. MSMichael Seibel11:10

        Like, you know, like, making an impact is going to create ripples, waves. I think the other thing that's tricky is that there's this meme out there that, you know, the first part of a startup is pushing the, the, the boulder uphill, and then the second part's chasing after it. And it's like, unfortunately, I think that meme has been midwitted into, like, I'm gonna have to work really hard for some period of time, and then I'm not gonna have to work hard after that, which I think is the dumbest interpretation-

    29. SPSpeaker11:37

        Yes

    30. MSMichael Seibel11:37

        ... ever. It's like, oh, yeah, the people running the most successful companies, like, they're just chilling now.
14. 12:01 – 13:03

    Tactical response: acknowledge the bad day, feel it, then don’t freak out

    1. SPSpeaker12:01

       And so to try to make this actionable tactically, my suggestion if you're having a bad day is to acknowledge it-

    2. MSMichael Seibel12:09

       Yes

    3. SPSpeaker12:09

       ... and to feel your feelings.

    4. MSMichael Seibel12:11

       Yes.

    5. SPSpeaker12:12

       And it might take you a day or it may take you a few hours to process. And I, we're not saying- Block out your feelings so you-

    6. MSMichael Seibel12:19

       No, no, no, no

    7. SPSpeaker12:19

       ... so you, so you have a meltdown. I think it's we're saying you should learn to take it in stride-

    8. MSMichael Seibel12:26

       Yes

    9. SPSpeaker12:26

       ... and consider it just part of the job. It'd be like if you were, you know, a doctor or a surgeon, you know, you're gonna lose some patients. You know, like, it's part of the job-

    10. MSMichael Seibel12:34

        Part of the job

    11. SPSpeaker12:35

        ... is that it's not all puppies and rainbows.

    12. MSMichael Seibel12:37

        Yes.

    13. SPSpeaker12:37

        [laughs] And that just knowing that that's the case, and hopefully watching this video and hearing us say it should make you feel better-

    14. MSMichael Seibel12:45

        Yes

    15. SPSpeaker12:45

        ... that this is just part of it.

    16. MSMichael Seibel12:47

        Well, and I think that bad days often open the door to the next big leap in your company, right? That bill that I was talking about, that's why Kyle sat down and he started building our own video system.

    17. SPSpeaker13:03

        Mm-hmm.

15. 13:03 – 14:22

    Turning the worst moment into a great experience: early Airbnb customer-service story

    1. MSMichael Seibel13:03

       'Cause he was like, "We can't pay these types of bills, so maybe we have to invent something." I remember a story from back in the day with Airbnb where, you know, they experienced a bad day. It was, like, one of their first international trips, and somebody was ... It was actually a woman, and she was gonna be going to France, and she was gonna be getting in late. And she, like, calls in customer service at 11:00 PM, and she's like, "The host isn't there. I'm screwed. I hate you guys."

    2. SPSpeaker13:29

       [laughs]

    3. MSMichael Seibel13:29

       "I knew this was a scam."

    4. SPSpeaker13:30

       Right. [laughs]

    5. MSMichael Seibel13:30

       You know, like the whole, you know, like-

    6. SPSpeaker13:31

       The whole thing.

    7. MSMichael Seibel13:32

       If you're freaking out in the middle of the night in Paris, and, like, you don't have a place to stay. And I remember that Joe would tell this story, who was ... You know, he was customer service. Like, his cell phone number, the founder's cell phone number was, was customer service. And he was like, "Step one, I'm on hotels right n- hotels.com right now. We're gonna book you a hotel room."

    8. SPSpeaker13:49

       Yep.

    9. MSMichael Seibel13:50

       And it was like, "Step two, in the morning we'll contact the host. We'll do the..." And it was just like how you turn the worst call into, oh, bam, like, we're gonna make this a good experience. We're gonna make this a surprisingly good experience. To me, like, bad days have the ability to do that if you don't freak out. All right. Good chat.

    10. SPSpeaker14:11

        Thanks, Michael. [upbeat music]

Episode duration: 14:23