tptacek 1 day ago

This is all great. One thing I wanted to call out in particular is Thomas' take on investor verbal agreements. YC has a thing about this: it's called the Handshake Protocol.

The idea is: you and your investor agree on (1) an amount to be invested, and (2) a valuation or cap. Maybe you shake hands. Then, after the meeting, you memorialize the deal in an email. The deal is then socially binding: reneging on a Handshake Protocol deal is a big thing, gets noted in Bookface, whatever.

There's nothing magic or even interesting about the protocol; all it does is eliminate a form of ambiguity that professional investors are facile with and founders aren't. Investors are very good at saying "yes" and meaning "no"; they want the option to invest without the commit. If you don't put it to them directly, they'll take the option! The Handshake Protocol puts it to them directly: "are you committing?"

Most of the time, you're going to get a "no" answer to that, which is exactly what you want: clarity, so you can make decisions.

https://www.ycombinator.com/handshake

  • xyzzy_plugh 21 hours ago

    This is great, simple advice that is obvious in hindsight.

    It works in all sorts of places too! Like negotiating a job offer or a raise or promotion or time-off. It also works outside of the workplace such as following up with social acquaintances ("hey let's play tennis sometime").

    It excels at identifying the party unwilling to commit. And in my experience the sooner you figure that out the better.

    • tptacek 21 hours ago

      And "unwilling to commit" is fine! That's most people most of the time. The only problem is when there's ambiguity about the commitment.

  • The-Old-Hacker 5 hours ago

    We used to do this in the software documentation team I worked with for 9 years: we would discuss something verbally, then the person who'd called the discussion would summarise the conclusions in an email to team members. They could then edit the summary as needed. It really helped further down the line as a communal memory device.

jph 1 day ago

> there are two separate personas that you need to “create”: The user persona and the buyer persona.

Even more important: stop using personas, start using actual people. I've experienced many startups make unforced errors by conflating people into personas. A better way is to tag people with attributes, such as specific interests, explicit concerns, tasks to be done, usage goals, learning preferences, and the like.

When you switch from personas to actual people, it opens up many more product experiments-- many of which are surprising and may even feel counter-intuitive to founders. Increase your startup chances of success by carefully connecting with your actual users.

  • tdullien 1 day ago

    Definitely - but those are normally called "development partners" in B2B, right?

  • anticorporate 1 day ago

    Those two personas were very helpful to me in my previous life as a technical marketer; they helped me learn when to leave a job. Any time a company I have worked for told me they're shifting emphasis from talking about our product with the actual users to talking about "solutions" for the buyers, I knew it was time to start sending out resumes because the product was about to stall and the work climate was about to get insufferable.

  • josephmosby 1 day ago

    Wholeheartedly agree.

    Personas are useful for developing a general character that you can refer to. But you still have to be able to say "Alice Robertson, who is a demand-gen marketer at $CUSTOMER, is a prime example of this persona and someone we should talk to during product research." If you can't speak to an actual human and validate your ideas, then you are at risk of creating a fake persona who sounds just plausible enough to convince you to make wrong decisions.

aleph_minus_one 4 hours ago

> I love working with great people on problems just on the verge of the possible. This can be hard in large organizations, as large orgs tend to (unintentionally) avoid having too many good people on one team (the value for the large org is maximized by spreading out great people to guide many teams - so most teams will only have 1-2 great members).

The problem is in my opinion a little bit different: these good people would love to make the team in which they are working better, but are actually actively kept down by work colleagues and bosses. Thus, the organization does not profit from these good people, because is has no use for their greatness. Instead, this approach introduces a lot of (political) infights into the teams, where often the good people are treated as the evil troublemakers at the end.

ramon156 1 day ago

I resonate a lot with these reasons. I definitely know I am not the most optimal employee, but often times the people I clash with are people that I cannot respect. Either

- They think they're higher than me (you cannot collab like that)

- They want it their way, despite there being multiple ways to Rome, and will cut off the conversation with orders, not arguments

- They pretend to be technical and are only making the bureaucratic back-and-forth worse. You can definitely tell when someone knows what they're talking about

Sadly a lot of companies will reward these type of people by putting them in the high seats.

  • avmich 1 day ago

    "Their way" - some way has to be chosen, without too many back-and-forth.

    In addition to technical there could be other reasons to prefer a solution. Some of those reasons can't be stated - for various reasons, like privacy or intuitiveness.

    There are some reasons people like that are rewarded, and not all of those reasons are bad.

  • feoren 1 day ago

    > They want it their way, despite there being multiple ways to Rome, and will cut off the conversation with orders, not arguments

    I don't know about your experiences, but insisting on this point can be a death sentence. I've spent most of my career as "technical lead", carefully building an approach that works for what my team does based on an underlying theory that is very difficult to verbalize. I've found through experience that when I feel like the project is aligned with this theory, the project goes very well, and when it's not, it doesn't. I've considered thousands of small tradeoffs over 15+ years of developing these ideas.

    At this point in my career, I've found that trying to explain the rationale behind my decisions is a losing game. It's a careful balance of a thousand factors that I'm constantly weighing and adjusting. If people share my goals and are interested in learning, great! I'll make some time to talk through parts of the theory with them. But it's not always during project time -- sometimes you just have to trust me.

    Yes, you thought of six different ways to do it -- I probably also thought of those ways. I'd love to live in a world where we can have a quick conversation about them and then all agree on the path forward, but that's not how it works. In reality, whoever I'm talking to goes into "argument mode", focuses on irrelevant details, argues about the names of things instead of their substance, takes things personally, feels ownership of whichever idea they came up with first, etc. They say they just want to learn, then they expect me to transmit 15+ years of thinking into their brains in a short conversation, while they argue with me on every little point.

    There are a thousand ways to do anything, which means it's critically important to reject most ideas immediately. That often means hurt feelings. It's just better to have the person with the vision making the decision. If you don't want to go with my vision, my theory, that's fine: go with someone else's. One other person's vision, and then don't argue with that person either.

    Of course there is room for discussion, feedback, learning, and debate, but this may be better done "off cycle".

softwaredoug 1 day ago

I see a pattern where companies end up becoming consulting firms with a bit of proprietary tech. Then all their efforts are put into a handful of clients. The companies call them “design partners” but they’re basically clients.

Seems like a particularly risky trap for bootstrapped companies desperate for revenue. At the same time the best companies I see out there are relentlessly customer focused.

How do you draw the line between “design partner” and becoming someone’s consultant.

  • hylaride 1 day ago

    This rings true. A previous job I had did email analytics for the investment banking industry (from boutique firms up to the largest banks in the world). I kid you not, the single biggest driver of our success was the simple fact that our expertise in email meant that we fixed problems that almost all these firms had with email deliverability (bad IPs, SPF/DKIM/DMARC, broken unsubscribe functions, etc) over the actual product itself. This was in our best interest as our product was useless unless recipients could get email delivered to those that wanted it, but it was eye opening.

  • tdullien 1 day ago

    You don't have a product until there's ~3 customers, with perspective to more. Before that you're essentially a consultant. I'll add that to the next version of the doc, too.

    The point is: For anything you build, you can find 1 customer. It's only when there's multiple customers that like the product and want to improve it where you move from "consulting" or "custom development" to "product".

  • lubujackson 1 day ago

    That comes down to the ability to say no (or at least "not yet"). I have seen lots of startups that land a few mid or big clients and lose the plot by serving every throwaway request the client makes. Doing this slowly turns your product into a bespoke solution not fit for others. There needs to be constant tension between the product goals and its application, and holding that line will always, always annoy a sizeable swath of users.

    Apple famously ignored users on lots of fronts: can't manually add RAM, mouse has 1 button, etc. They didn't serve one type of user specifically so they could appeal to a larger market. You can't serve everyone.

mrkiouak 1 day ago

Excellent writeup from someone who clearly cares about hitting the intersection of "good for customers, good for himself and investors, and good for employees".

We'd be much better off with people thinking and acting in line with this!

softwaredoug 1 day ago

Maybe a simple question I didn’t see here: paying yourself a salary?

How true is it you’ll need to persist under extreme duress unable to pay yourself a salary? Relevant for us with kids / families where we provide the family’s income.

  • tdullien 1 day ago

    I will add a section. Pay yourself a salary at the very latest the moment you've raised funding. If a VC objects to you doing that, get a different VC. You're in for the long run, and support from your family etc. is important, and you're already taking on a huge risk by pooling all your risk in one company, vs. the VC who is happily diversified.

    Investors who imply you shouldn't take a salary are no bueno.

    • insanitybit 1 day ago

      I've never once had a VC even ask about my paycheck let alone suggest I don't take one. FWIW the second you run a company you literally have to pay yourself at least minimum age, it's illegal not to. edit: Hm, apparently you can take a literal $0 paycheck. Regardless, it'd be absurd for a VC to tell you to do this imo.

      • mhluongo 1 day ago

        This clearly isn't true for eg a single-member LLC, and likely not true in general.

        • insanitybit 1 day ago

          If you're raising VC money then I assume you're not an LLC. But I think you're right that the owner can take a $0 salary.

      • pixel_popping 1 day ago

        It's not true, as the founder of the company, you aren't even technically employed (unless you become a legal employee), so there is no concept of wage at all, only dividends and buying stuff directly with the company (fine within reasonable limits).

        • insanitybit 1 day ago

          I feel like I was an employee, I don't really recall the details when I spun up my C-Corp tbh. It does seem that a CEO can take a $0 salary.

    • softwaredoug 1 day ago

      How much of a salary do you pay yourself?

      Like equivalent to what your developer salary would be? Less? More because you’re a CEO now?

      I basically have minimum $ amount I would accept for “developer job I absolutely love” that I know sustains my family comfortably without much extra fun or savings. Is that a good bar?

      • tdullien 1 day ago

        Yes. Usually, the VCs will want you to not take an extravagant salary, but a solid family with which you can keep your family comfortable. And that's normally the right bar.

        And if there are liquidity pressures a few years into the process, and you have traction at Series B or C - don't hesitate to think about a small secondary.

      • insanitybit 1 day ago

        I basically specified that I'd make the highest salary and no more than that. It felt like a fair policy at least, it took a lot of guess work out of it. If I wanted to bring someone in at X00K, I had to make X00K.

        I started off making significantly less than I did as a dev (~30-50k + I had spent months with 0 salary before raising), within ~2 years I was making a bit more and I capped out around there.

    • pixel_popping 1 day ago

      Absolutely you should take a salary, one that don't create anxiety and making sure you aren't struggling every end of the month, you don't want a Founder that keep thinking of building another project than the one funded because he is struggling for a matter of thousands a month.

  • tptacek 1 day ago

    I'm not sure austerity wages for founders are really a thing anymore. Serious investors understand that team turnover is as or more scary than fiscal drama.

    There was a longstanding "ramen profitable" ethos on HN, but part of that is rooted in a much older set of YC deal terms and lower expectations for seed rounds. But YC is now one of the principal components of all tech startup funding, the standard terms are much better, syndicated seed rounds have gotten pretty big; I think you're expected not to be silly about comp, but I don't think people are looking for you to signal commitment or virtue or asceticism with your comp package.

    If you can't pay yourself a real comp package, something is probably wrong with your business.

    • thepeoplebook 17 hours ago

      A stable home life is a prerequisite for focused startup work; otherwise day-to-day worries take up too much attention.

      • doc_ick 17 hours ago

        Agreed, you need to have a clear mind and not too large of a sum to focus on work; for example making an Oreo pie.

aetherspawn 6 hours ago

I don’t know about the advice on market size… nearly every 2nd founder says go into beach head markets and stay away from markets with high competition.

The ones in beach head markets seem to succeed more often on average (anecdotal)

The-Old-Hacker 5 hours ago

"Great people are sometimes oddly-shaped"

Great people are racehorses, not donkeys. And racehorses tend be skittish. But they win races for you.

FreakLegion 14 hours ago

> “we really do not want any distraction now, if you feel that strongly you can always send an unsolicited term sheet to the board to consider”

Nope, don't do that. If you receive a credible term sheet at a meaningfully higher valuation, you'll have to rerun your 409A, even if you don't take the investment.

  • tdullien 13 hours ago

    Good point, will add that. Thanks!

airocker 1 day ago

Great article. Few suggestions:

- If you are bootstrapped, you can build dual use technology. - All of this is predicated on the idea that building software is hard, you need 8 years to build a product that people like. Maybe this is all going away in the AI world in a couple of years.

  • tdullien 1 day ago

    I don't think you need 8 years to build a product people like, Prodfiler got good resonance and we built it in ~18 months, it would probably take 4 months now...

horticulturist 1 day ago

This is really well written and clearly from someone who has loved through it. I think just about all of their observations are correct (except for getting a coach - incredibly detrimental in my experience).

  • tdullien 1 day ago

    Author here. I'd be curious what went wrong in your case? (Also, happy to soften that advice further if there's strong evidence that people find the advice detrimental).

    • faeyanpiraat 1 day ago

      Not OP, but when I did my startup I also tried coaches, and the first one I talked to was kinda like what gold diggers would be in a relationship context (asking high price, since he knew we raised, and in the demo sessions provided superficial value), then I finally went with one who actually had business experience and uni degree in psychology and provided modest but solid advice for a fair price, that was quite helpful in those difficult times.

      So I guess spot and avoid sweet talking charlatans (this applies to all business relationships though).

      • tdullien 1 day ago

        Yeah.

        Also - I use the term "coach" broadly here. Many people react very poorly to the term "therapist", and "coach" is a much broader term encompassing both therapy or just people that have significant experience in a field. Or just an older relative or acquaintance that is willing to provide regular advice/feedback.

        There's definitely charlatanism, particularly when people advertise themselves as "business coach" or "startup coach".

xvilka 23 hours ago

Looks great, but the passage about Google CEO is unnecessary in such guide, IMHO. Even if it might be true.

frabia 1 day ago

Great article! One question: you talk about market size, but you don’t address the existing competition in the space. In my opinion, two equally sized markets can have very different levels of competitive pressure.

Is that something you factor into your playbook? Or do you simply not find it relevant to judge whether to enter a certain space?

  • josephmosby 1 day ago

    (not the author, but here's how I think about it)

    Assuming that you're not a commodity product, it all kinda nets out in the end. If you have a competitive market, you have proof that people want your product at a good price, else no one would be in the market. If you execute better than all of your competitors, then you can theoretically take every last penny of that market.

    I don't think the competitive pressure changes the decision whether there's revenue to be made in a certain space, though it may change the personal decision if the operating tactics required in a competitive market are personally fun for you the human being.

  • tdullien 12 hours ago

    I should add something about this, but if a market looks like a drunken bar fight, I'd probably not want to go there.

    That said: A good market will become crowded quickly in either way.

tamimio 20 hours ago

I love it, amazing article! All the reasons listed apply to me and a while ago before realizing that a lot of other entrepreneurs share the same mindset, I always thought I am a loser unfit in any company I worked for, especially the interviews part, i simply suck at them, period! but I do wonders given the chance. I am just glad I don’t have to go through that anymore.

alexashka 1 day ago

If you have a thing people want that you spent a decade making that isn't easily replicatable, the rest doesn't matter.

If you don't have that, the rest also doesn't matter. Unless you're obsessed with money, in which case, you are very confused and should not be guiding anybody to anything.

Guides regarding minutiae from lottery ticket winners are tiresome. I think anyone over 30 has learned what these 'guides' amount to from looking at Paul Graham.

  • orphereus 21 hours ago

    That is oversimplifying it to the extreme.

    Like the example with the doctors and how to find actually good ones, you can add this essay to the list of enterpreneurship tips you can compare and decide for yourself what is useful and what isn't.

    • alexashka 20 hours ago

      Thank you. Before you said it, I didn't know what to do but now I know to compare and decide for myself what is useful and what isn't.

      I hope my newfound way of life is not oversimpifying it to the extreme.

oliver236 1 day ago

why did the author put the tickers for the companies he sold to?

  • tdullien 1 day ago

    Good question. I think I did it to indicate that we sold to public companies.

    • rulesilol 1 day ago

      Google (GOOG) is a public company? Color me surprised. I'd always thought it was just a mom and pops shop.