Update (October 2nd, 2024): I have had this invitation up for approximately 12.5 years at this point. During that time, it has resulted in approximately low X,000 face-to-face meetings, mid X,000 calls, and low X0,000 emails (from me). I am in a different season of life now. I'm blessed with a wife and two children, for example.

As my availability has waxed and waned, this invitation has been a source of stress. Even though I explicitly did not promise everyone a reply, every time I had to prioritize my own schedule above the marginal request, I felt bad.

Thus, a new experiment: I am releasing myself from the implicit commitment here. I will try this out for a few months and see if it suits. You are still welcome to send me email. But I intend to be more aggressive about prioritizing it than I have been in the past, and that will likely result in less total hours spent on this part of my life, relative to the other parts of it.

I was once a shy engineer with a pathological fear of annoying people by contacting them. I eventually got over it (some days more than others, to be totally honest), but notice the same tendency in a lot of young engineers and other folks interested in the software business. Thus the following offer, which I’ve made since 2012, and which people take me up on several times a month to this day in 2024:

This is a standing invitation: if you want to talk software, I want to talk to you.

My email addresses are patrick@ any domain I control, including this one. I strongly prefer email as a communication method over messaging services.

• I like getting email. I have never, not even once, regretted getting email from a startup, engineer, student, or person interested in our industry. There is absolutely nothing you can do in my inbox which will cause me to think poorly of you as a person or make fun of you to my friends. The worst thing that has ever happened from someone sending me an email is me being a bit busy that day and not replying. Feel free to send me email. My rough estimate is that I read approximately 80% of it and get back to approximately 50%. (See below for tips on that.)
• I like reading things. If you write something worth reading, tell me. Again, the worst thing that has ever happened as a result of that is that I just don’t read it. All that cost you was a two-line email.
• I like making and selling software. This is doubly true of software which is relevant to my interests. A non-exclusive list of those would include A/B testing, analytics tools, and software for underserved niches. If you write software, SaaSes, etc that you think I would be interested in, feel free to send me an email. (n.b. Invites/license keys are nice, specific questions you have about the product are even better.)
• I like meeting people at conferences. If I am at a conference as a guest or speaker, my explicit goal for being there is to talk to you. I’m easy to spot: tall geeky guy with glasses wearing (90%+ probability) a red track jacket (my trademark after years of being Twilio’s biggest fan). Come up and introduce yourself. I have been told that people are afraid to do that because they are under the impression that I am a celebrity. I have, from time to time, done something worthy of acclaim. I also had a level 72 gnome mage at one point. I’m a geek just like you, trust me: say hiya.
• I enjoy meeting people in my city. As of August 2023 I live in Chicago, and not in Tokyo. (But if you go there, and you should, I have some recommendations). I don’t know whether it will be sustainable due to the relative number of folks who know of me in Chicago versus Tokyo, but in principle, if you’re up for a coffee somewhere near River North or Fulton Market I very likely am, too.
• I like meeting people when I’m on business trips. I travel fairly widely for work, a few times a year. If I’m in your neighborhood on work, feel free to invite me to say hiya, get coffee, etc. If I’m not busy, I’ll say yes. If I’m busy, I’ll just tell you so. I will warn you in advance: “If you’re ever in $CITY give me a call.” is unlikely to result in you getting called unless I specifically want something out of you. I generally announce on Twitter (@patio11) when I travel on business. I don’t do that because I have an overwhelming urge to tell the universe, I do it so that people in the neighborhood will feel free to say hiya.

• I don’t like telephones. If you want to speak to me by telephone, marry a McKenzie.
• I don’t do work via Facebook. I’m fighting a losing rearguard action on this front but, well, get off my lawn.

Generic Tips For Emailing Busy People

• Specific questions are better than vague requests. Here’s a vague request: “I was wondering if you could mentor me.” What does that mean? It sounds like an unbounded time commitment on my part, and I have no clue how I could provide value to you. Here’s a specific question: “I have a new SaaS in the $FILL_IN_THE_BLANK space. We’re investigating customer acquisition methods, and having read your posts on SEO, I see that I need more links to rank for competitive queries. I’ve got three ideas for linkbait: $IDEA1, $IDEA2, and $IDEA3. Can you give me any suggestions on how I can get the maximum bang for my effort-based buck on these? Do you have any other suggestions for linkbait pieces in this space? Thanks!”
• If I don’t respond, that is probably because of me, not because of you.Trust me, I don’t hate your guts. Do the math: your email, 5 minutes, my life, 1,440 minutes a day. If I don’t write back, the overwhelmingly likely reason is that something in the other 1,435 minutes caused it rather than anything you said or didn’t say, or anything about you personally. Maybe I’m crunching on a project, maybe I’m out at the park with my children, maybe I’m buried deep in a book. Feel free to ping me later and ask if I had time to think about the first email! Again, you won’t annoy me. The absolute worst case scenario is that I’m still busy, but as you might have noticed, I have a lot of free time and if you catch me in the middle of it I will probably write back.
• I intentionally keep email off my cell phone (because otherwise I would get pushed work every hour of every day), but Twitter @ mentions actually raise a notification.“Hey Patrick, did you see my email last Tuesday which included the words $EASILY_SEARCHABLE? I’d love a reply if you’ve got time.” is a very effective way for you to get prioritized to the top of the stack if I’ve got a few minutes of free time.
• Asking for introductions to people is tricky. I may know some people who it would be useful for you to know. Pretend I have an account of reputational capital with each of them: introducing anyone to them is a draw on that account, and if the introduction goes really really well I get the capital back with an added bonus. If, on the other hand, I overdraw my account, then they stop reading my email. This means that a) I want to introduce the right people to the right people but b) I don’t want to introduce someone I don’t know well to anybody, in particular, to anybodies who a lot of people are trying to get in contact with.
• Restrained, professional confidence is a good skill to master. Don’t apologize for contacting me or wasting my time — avoiding that is the whole purpose of giving you an engraved invitation to contact me. Don’t minimize your own experience, competence, success, or chances. I give people advice on selling things for a living — you will not offend me with restrained salesmanship about why I should care about your email. “We’re revolutionizing the ability of people to connect with data” doesn’t mean anything to me and will not predispose me to doing things for you. “Our new A/B testing software is easier to use than the one you wrote because $REASON1, $REASON2, and $REASON3″ will certainly get my attention if those reasons are credible.
• People love to back underdogs but they hate backing losers. This is closely related to the above point about confidence. No matter what stage you’re at, your business is already bigger and more successful than I was at one point in my life. (And many folks who I talk with could lose my business in the petty cash drawer, even today. See above regarding not-an-unapproachable-celebrity.) Do not minimize that: concentrate on what you can do to get to the next rung. Not from the US? Trust me, I won’t hold it against you. English your third language? Spiffy, I speak three myself, and your English is probably superior to my Spanish if you got this far. Is your product a little niche? I sell bingo cards to elementary schoolteachers for a living. I appreciate folks with a can-do attitude who look like they are going places and will benefit from specific suggestions that I can give them. Conversely, “Woe is me, I am not in Silicon Valley and cannot get funding and do not know anyone and am not a programmer and I am unemployed and I have no prospects and I did not graduate from a good school.” is not likely to endear you to me.
• Concision is a virtue. I’m terrible at it, obviously, but that doesn’t mean I don’t appreciate it. The optimum length for a first email is probably about a paragraph, and the optimum number of decisions you ask me to make in an email is one.