I'm Patio11 (Patrick McKenzie), creator of Appointment Reminder. AMA!

For those who don't know me well: Starfighter was the first software business where I was actually pitching to folks who knew me from my blog/etc. This made life SO MUCH EASIER that it is difficult to overstate. (We closed tens of deals on 1~2 phone calls apiece and basically never had to worry about market risk.) I highly recommend that.

AR and Bingo Card Creator were entirely disjoint markets, which was intentional, since after running BCC for a few years targeting elementary schoolteachers I didn't want to serve that market anymore.

My main strategy for getting customers for AR was ranking for the exact match [appointment reminder], which I quickly ranked #1 for on the strength of the domain name. I wanted to repeat my success from BCC for making scalable content targeting every variant of [X appointment reminder], [Y appointment reminder software] etc for every industry/profession X, Y, and Z. For example, "dentist appointment reminder."

I didn't successfully execute on this to the extent that I did on BCC, partly due to lack of early success, partly due to the Google gods being fickle, and partly due to never really having my heart in it.

I think careers are ~45 years long.

I spend the first 6 years of my career learning something one can learn in 6 weeks of experience or 6 seconds of reading: don't work for a traditionally managed Japanese company. This is the only decision I really regret.

I spent the next 5 years (2010 ~ 2014) going from passable to pretty good about executing at SaaS businesses, mostly as a function of consulting rather than from the experience points gained on Appointment Reminder.

I spent ~2 years swinging for the fences on Starfighter. Partly that was because I wanted to try my hand at something which would have an ambitious outcome for myself/my family in a success case. Partly it was because, ~10 years, I was a bit worried about "Will any of this actually matter when all was said and done? Clearly I do not get up in the morning to optimize the seating charts at dental practices."

I see my term at Stripe as a continuation of the same search for impact on the community I care about (which is "people who work for the Internet", broadly defined, and which is all of y'all, Atlas users, and the folks who would look at Starfighter's programming game and say "Ooh relevant to my interests").

I think it is highly, highly likely that my next adventure is directly in the service of the same community. I've learned that I'm so, so much happier when working for it (both at Starfighter and at Stripe), and that serving it is much easier than parachuting into a new B2B vertical and trying to sell software to e.g. dentists.

Whether it will be a swing for the fences startup? 5 years ago I would have told you I'd never have a job again and here I am. Who knows what I'll tell you in 5 years from now.

I intend to! I am just quite busy with work and with having two young kids. Also, my "writing process" has always been heavily dominated by "just write about what you've been doing recently" and sometimes my work at Stripe doesn't lend itself to talking about publicly.

If you like my writing, the current best place to catch it is on https://stripe.com/atlas/guides -- I'm on track to publish about ~4 of them this quarter.

My agreement with Stripe, which both parties are satisfied with, precludes me from doing for-money side projects. I don't really have the bandwidth to do them between work and having two very young kids at the moment.

A thing that I do which scratches the same itch for me is use the fact that Stripe lets people contribute to parts of the company which are relatively far from "their day job." I've described the machine that is this company as an MMORPG made out of money. Every once in a while I steal a few hours or a day or two from my actual projects and take a run on one of the (numerous!) levers that can be adjusted to great effect here. It's really fun.

BTW we're hiring and I'd always love to chat with folks!

I actually did reply to an RFP from the State of Hawaii once. It was surprisingly straightforward, at least at the $X0k a year level. They publish a list of requirements; you say that you are going to EXACTLY MEET the list of requirements.

I didn't win the RFP, since I bid 2X and a competitor bid X. I later learned that the competitor had won the same contract the prior year, so they didn't have to worry about custom engineering costs for the bid; if I had built my business around winning contracts like that, rather than saying "Hmm I anticipate this will take 3 weeks of engineering work and eff if I'm doing that for less than $X, add in $X for the software, so $2X total", I would have said "OK probabalistically if I win this bid I will do 3 weeks of engineering work in year 1 but keep the contract for five years, so I should build $0.2X ~ $0.3X into the bid."

I think that small entrepreneurs should be realistic about what percentage of their day-to-day chasing government contracts and implementing not-too-wonderful requirements will be if they go down that route.

You can sign up for the Hawaii RFP website and take a look at the sort of things they buy. Small businesses already serve them quite a bit on things as diverse and uprooting military statues and providing jumpsuits for prisoners with the cords removed to avoid weaponization. It wouldn't be how I chose to live life or conduct a business, but clearly people are making it work, just like someone figures out how to sell printer ink at a markup to every City Hall in America.

In between you asking this question and today we published our Stripe Atlas guide to the Business of SaaS, which answers this and so much more! https://stripe.com/atlas/guides/business-of-saas

Informally, visitors to free trials is the roughest number to estimate there, since it is incredibly sensitive to the quality of visitors you're getting to the page. If you put a gun to my head I'd say "Uh 5% for card-not-required assuming you've got a worksmanlike mix of marketing things going on." Estimates for free trials to paying customers are in the above post and depend on e.g. whether you require a card upfront.

Talking to people and reading. My base rate of reading is pretty high; the thing that I have to force myself to do 10X or 25X more than I would do naturally is opening up conversations with folks in various walks of life and asking them about what makes their businesses interesting, challenging, less-than-maximally-satisfying, etc.

Here's an exercise you can do: do you understand what a life insurance agent does all day every day? Make it your mission for a week to do so, well enough to explain it to a close friend who has no access to your sources. All you have to do to learn this is read and make conversations happen. (People are happy to talk to you!)

I was lonely in central Japan and wanted people to talk to about this new fascination of mine, running an online business, and my blog (and later HN) was the outlet for that. It wasn't obvious to me for at least ~5 years that it was creating something valuable that I would take with myself for the rest of my career, for much the same reason that it wasn't obvious for the first 5 years that BCC was a business and not just a quirky hobby that happened to pay money.

I'd encourage y'all to understand that whatever you're working on right now, you will build capital (skills, reputation, a body of work, technical assets, email lists, etc) that makes everything you do for the rest of your life better. You can make choices to optimize how useful the current thing is for you.

For this at more length, see my talk at Microconf 2015 about Leveling Up. Top-left corner of here: http://www.microconf.com/past-videos/

I talk to a lot of people who want to be Elon Musk when they grow up. That is not a desire that I vibrate with fellow-feeling for, but suppose one sincerely wants to be Elon Musk, or to make software as widely deployed and influential as Word.

If you want to be Elon Musk, you want to develop financial software for the Palm Pilot. If you want to write Word, you want to start with Altair Basic.

You then layer on top of those early successes with carefully considered Next Big Things which eventually ladder up to whatever your endgame is. (Though Elon Musk would probably tell you that he is about 1.5 AU from his endgame, at least based on published reports. Word was, similarly, not the most important thing Microsoft ever published; that was probably Windows 95 or IE4ish when you consider on a long-enough timescale.)

When you're doing the leveling-up step, you get to choose again whether you're going to bootstrap, take VC funding, join forces with a company which already has the capital problem licked, etc. I think people don't appreciate how long a career is (45 years!), how many shots you get during it (at least 10!), and how you can change your answer on the funding structure over time.

I never considered taking funding for BCC, considered it for AR and Starfighter, am currently working at a relatively well-funded company, and know that, if I decide I want to tackle a problem which has a minimum buy-in of 7 figures for my next thing, that I have a reasonably good pathway to using what I've learned and built and who I've helped to convince professionals to help me find $PICK_A_NUMBER.

I love the idea, but I feel like from a sustainable business angle it's a long shot.

There are a lot of sustainable businesses built on selling content to parents who care a lot about their childrens' education. Just look at how many different firms produce actual physical goods that are sold at e.g. science museum gift shops, or how many people write books on even sub-genres like "getting my daughter more interested in engineering." (My daughter's favorite: Rosie Revere The Engineer, which is certainly not the last word on that genre. She likes the helicopter with string cheese. My budget for exciting my daughter and son about ways to use math and science for goodness is high.)

Fundamentally you want to convince 1k~2k people to pay $100 a year for this offering, right? You can find that many well-monied working parents who care about getting their kids into computer programming at Google's HQ, alone.

I realize I'm bucking your advice about finding something companies will pay handsomely for

How would you pitch it as an employee benefit? ;)

Here's how I would do it: "You know that your company skews young historically but, as your early cohorts age, they are increasingly getting into the raising children stage of their life. Foosball and after-work happy hours are no longer maximally attractive to them. You know what is attractive to them? Being able to share that passion for the thing they're great at with their kids. You know how $FIRM can facilitate that, letting your workers understand that you also appreciate both their professional ability and their consuming drive to give their children a leg up? By licensing the $YOU content library. For only $25 per engineer per year -- less than the cost of a single meeting -- we will..."

Hello, person from the Internets.

I feel very strongly about maintaining the ability to talk to people who don't know me, which is why I published this policy many years ago: https://www.kalzumeus.com/standing-invitation/

You should know that I get a lot of email from a lot of people. Like it says on the standing invitation, it is almost never the case that I don't reply due to something someone said. I have probably replied to thousands of people since my interaction with you, and not replied to thousands for no reason more complicated than "Life gets busy; that's why I message a 60% reply rate." I do not remember our interaction. Even if I did remember it, I would not hold it against you, because I have been (and am!) a socially awkward geek myself and I know that it is not the case that 100% of my utterances are my best work.

Which is a long way of saying "No apology required" but which I wanted to elaborate on in depth because I think it is representative of how people who want to build businesses should think about cold outreach. The people who you want to work with are worried about your outreach far, far less than you are. Send more than you're comfortable with; sweat the outcomes less.

Anyways, here's a more specific one: I'm trying to grow my consultancy and unearth problems in the facilities industry where a SAAS product thrives. I was wondering if you have any suggestions as to how to incentivise people to get on the phone and answer my questions.

I've been playing around with the idea of surprise rewarding someone after I get their feedback, what do you think of that?

Well if you do it as a surprise, it certainly can't motivate them to do the thing you want them to do, right?

I would offer the rarest, most valuable of things: a sympathetic ear from someone who is hanging on the speaker's every word. The only thing you need to get informational interviews is to present as someone who has done their homework, sincerely wants to learn more, and will be a good interlocutor for 30 minutes. Many people, even people who have more money than they know what to do with (and would not be motivated by $100 on Amazon because what does Amazon sell that they value and yet could not trivially afford), do not have their desired number of great conversations per week. Offer them that.

You should absolutely feel free to do things that other people are doing! Particularly for professional education! Many people have taught math. Not everyone in the world knows math yet. The work continues!

I am impressed by the folks at e.g. interviewcake.com with what they've done to educate people about coding interviews, but you can imagine many form factors for that content, many submarkets for it, etc.

Is the right thing for a middle-aged person contemplating a career change from an allied trade (e.g. electrical engineering or DBA) the right thing for someone graduating from Stanford? Probably not. Does every graduate of Stanford in 2020 learn in the same way as every other? Probably not. What if my real problem is not performing on the coding interview but it is getting past first-stage filters?

There are a million takes on potential businesses here.

The market is massive: AppAmaGooFaceSoft will hire ~100k developers this year by themselves. There are probably ~3 million professional software developers in the US, and more aspiring ones, and that pool is getting larger over time.

I look forward to seeing what you build / write / etc on this! It is very relevant to my interests.

Talk to people, talk to people, talk to people.

Who do you want to spend the next five years of your life working with every day? Talk to THOSE people. (Bias towards ones who work at businesses which have budgets. I like talking to geeks who program and I like talking to geeks who play D&D, but I don't want to build software for D&D players, since they have not rolled a natural 20 on finding a budget to pay for software.)

We have a policy at Stripe that we ship first and announce timelines later, since ordering it the other way inevitably causes sadness when things slip for reasons beyond your control. I strongly advise y'all to not announce ship dates for things which are not totally in the bag already; it will make your entrepreneurial lives easier.

You can reasonably assume that, since we hope to incorporate a majority of all Internet businesses worldwide, that we're working on everything needed to make that happen, and LLCs are a great business form for many entrepreneurs, so... well if you follow me on Twitter or sign up for one of Atlas' mailing lists at https://stripe.com/atlas, I promise we will not be quiet about things relevant to your interests as a business owner.

Developers can clearly pay money to improve their professional outcomes. There are 3 million developers in the US.

Can you convince them that written communication skills are as rewarding to them, for all possible understandings of rewarding, as learning Javascript is? Then that's a very promising market/business.

I think I'm bad at website design as a visual artform, and (in addition to having a bit of envy for people like IndieHackers or the Stripe Design team who are actually good at it) I choose to just consume their work, for example by paying designers or using templates to accelerate building new products. (We got incredible mileage for Starfighter out of a $15 Bootstrap admin theme. We would have eventually hired a designer if it worked out.)

I'm better at design from a conversion or information architecture perspective, largely as a function of having done it a lot for a variety of companies with relatively similar business models / audiences / etc. If you point me at a pricing page, I can generally make it better. (Point me at a pricing page, anyone!)

Are you A/B testing, growth hacking in any way?

Stripe would be disappointed in me if I were not moving the needle for the business in at least some fashion. The specific set of tactics I'm experimenting with changes with the opportunity, my mood, what other people I am working with are good at, etc. You can reasonably predict that at any given time I'm doing "my thing" and that I'm not entirely happy with how much of "my thing" I am doing relative to all the other forms of work I am doing. (The market appears to call my thing "growth hacking" but I do not love that term and do not self-identify with it.)

That's an excellent question. I don't have a great answer for you! I spend a lot more time working on low-touch than I do on high-touch. You know who would have an answer for you? Steli Efti and the folks at Close.io :

http://blog.close.io/cold-calling-conversion-funnel-analytics

I'm going to refrain from opining deeply about a particular identifiable business' pricing decisions for a number of reasons.

I would encourage folks starting businesses to spend less time closely scrutinizing decisions made by firms which are not directly related to their own, and instead attempt to understand the logic behind them and how the underlying logic applies to your own firm.

Stripe Atlas will shortly write in more detail about SaaS pricing. Broadly speaking I am strongly against unlimited anything when selling to businesses; it leaves money on the table. I will note that the division of money between a Relatively Big SaaS Shop and a Relatively Small Design Agency has different moral and tactical intuitions for me than the division of money between Somebody Scraping Out A Living On The Internet and A Company Which Can Afford Payroll For 10+ White Collar Professionals.

That question appears to be incredibly broad as worded.

I'm glad that I don't have to work with teachers on a daily basis anymore. I love teachers and they do very important work, but serving them as customers brings a bunch of headaches (technical literacy, limited ability to directly improve outcomes because of how they're hemmed in by The System (TM) and their students, etc). I find that I enjoy working with people who work for the Internet a lot more.

I broadly think that we could substantially improve childhood education, including through judicious adoption of software, but it won't be the problem I devote my career to. I wish those who do the best.

I'm constrained about how much I can tell you about BCC's performance that isn't on the Internet already, since I agreed to not spill the beans when I sold it to someone.

I am not constrained in telling you that I would probably not do seasonal microsites for any new projects.

I have struggled with procrastination throughout my life, and I don't know if I can tell you anything about it which is novel to you. In my experience it is never about the specific tactical thing that one isn't actually organizing oneself to do right now, and more about one's general happiness/energy/health levels, the degree of actualization one gets from the totality of one's work, and various other factors difficult to opine on without knowing you.

Should you Just Freaking Do The Thing? Well, gut check here: why are you working on making a woodworking course? Are you so enthusiastic about woodworking that the universe draws woodworking courses out of you naturally? That doesn't seem to be true. Maybe you are doing woodworking for the same reason I did scheduling for dentist offices, which is "Ehh it seemed like a reasonably good idea and sure sounds like a business." I spent large portions of 5 years not doing what I set out to do on that business.

I thought "Hmm, maybe something is wrong with me. I was able to organize myself to sit down and write content before. I can't anymore. Am I broken?" Nope; I was more productive at Starfighter and Stripe by orders of magnitude, not primarily caused by being engaged in the business for more hours (though that is, regrettably, a thing for both those experiences); mostly because I just care more.

I would encourage you to do the soul-searching and find something where you care enough about it to successfully motivate to do the grindy bits.

What learnings helped you get to that goal with your first software business?

It was a combination of doing things the long, slow, dumb way and waiting for passive sales via SEO to result in a number which approximated my (low at the time) salary, and getting comfortable with the notion that I had gotten myself to a place where my skills were genuinely valuable and that I could capture radically more of the value if I optimized my business to expose me to opportunities which made good use of those skills and then actually asked for more of the upside.

One of the reasons I wrote about salary negotiation ( https://www.kalzumeus.com/2012/01/23/salary-negotiation/ ) is that nobody ever sat me down and said "Patrick: the world is happy to pay dearly for smart people who learn how to do hard things, but if you sell yourself short, it is just as happy to shunt you into a $30k a year job doing absolutely nothing interesting and then make it seem like there is no obvious way out of that situation."

Any recommended resources on how to 10x your customers for the first time and going from 10 to 100?

I'd love to revisit that topic in substantial depth at some point. Thanks for the suggestion! Can I encourage you to sign up at https://stripe.com/atlas/guides to get an email when we publish on that (and related) topics?

If a business will pay $20k for it, then $20k is the better of those numbers... but would they pay $25k? Is it that valuable?

Your cost in creating it, whether in hours, brainsweat, or monetary business inputs, is probably not relevant to how you should price it.

You (broadly, indiehackers) should never ever ever assume you are charging too much or that you have discovered the true ceiling of all similarly situated companies' willingness to pay.

I always feel a bit meh about exclusivity, as it feels like a manufacturered imposition. That said, it works; perceived exclusivity repeatedly raises conversion rates.

I would probably approach this from the perspective of "If I'm not releasing this to the entire world immediately, what is the concrete reason I am doing that that is also in my customer's best interests? And how do I maximize value generated by the high-bandwidth interaction with a limited customer group?"

I absolutely think that you should offer e.g. concierge onboarding to your early customers, and given that you're likely bandwidth limited on being able to offer that in the early days, that is a perfectly legitimate reason to say "We are selling software but I only have 10 slots open at the moment and when they're gone it will be weeks before another one opens up, so if you want to get this solved immediately, $CALL_TO_ACTION."

I wouldn't materially update my advice here:

https://training.kalzumeus.com/newsletters/archive/enterprise_sales

I guess it depends on how you're rating it.

People want to buy from people they can trust. At least some people who purchase from Binomial (an enterprise middleware for video game companies which does texture compression) do so because Stephanie Hurlbut nails their "She is clearly good people and, therefore, this compression middleware she wrote will crunch the heck out of my textures." I know many people who are less dramatic examples of this.

At the same time, it certainly isn't a requirement to have a personal brand or outsized public persona to sell B2B services. You've never heard of my accountant. His company will do 8 figures USD this year based on competent execution of boring services work. They theoretically speaking have a company Facebook account; the relative level of awesomeness is not The Internet's Leading Authority On Japanese Income Taxes but rather We Are The Only Accountants In Tokyo Who Would Put Photos Of Our Christmas Party On Facebook #DealWithIt.

(If anyone needs an accountant, lawyer, or immigration specialist in Tokyo, hit me up; they're fantastic.)

Any tips on finding an accountant or lawyer? It doesn't seem most of them are very responsive.

Referrals; find someone in a situation similar to yours or a step or two down the line and ask them "Do you know an accountant / lawyer who you like working with?"

Be prepared to get a lot of "OH GOD THEY ARE ALL TERRIBLE" responses to this question. When you finally meet one who isn't terrible, hold on for dear life. (Isn't it funny how many geeks pay thousands of dollars to professionals who do barely servicable work on the expense side of their ledger and, on the revenue side, worry whether anyone will pay them hundreds of dollars for services which actually work?)

I found my Japanese accountants at my co-working space; I was talking to a startup founder DJ model Airbnb host (dude has a complicated tax return, is what I'm saying) and we started bonding as only two people who have filed their own tax returns in Japan can bond. Then he said "Oh yeah but I have accountants now." "Are they actually good?" "Love them." "I NEED YOU TO GIVE ME THEIR NUMBER NOW."

Plug: If you incorporate with Atlas, we'd be happy to refer you to accounting firms or legal firms which we've worked with to streamline the process for Atlas companies, which is a mix of technical work, process work, and "I spoke to a bunch of accountants so you don't have to."

How would you structure the timing of sales to a two sided marketplace where the value on both ends increases as both sides sign up - ie: the marketplace chicken and egg problem?

Worth a guide in itself. Someday!

Lastly, what's the most effective way to find a good mentor and/or co founder?

Vastly increase the number of in-depth conversations you have with smart people; vastly increase the amount of value you create for them in those conversations.

What's your advice for testing an MVP where you want to collect real money from customers but want to prove the idea before incorporating?

What is the reason for wanting to collect "real money" and what sort of money is "real" to you? If it is to impose market discipline on customer commitments, my general advice would be collecting LOIs. You could also collect but neglect to cash checks, or collect agreement in principle to pay you and "forget" to do the work required to collect payment (like sending an invoice) until convenient to you.

I try to avoid commenting on politics and it affects me relatively little from the perspective of living in Japan, but many US friends of my acquaintance would have had their business affairs materially improved by stabilization of the healthcare market in the US for people who do not receive employer-provided health insurance, and that appears to be other-than-stable at the moment.

This makes it relatively more difficult for folks who depend on health insurance to leave organizations which can afford it and start more productive organizations which, because of a concentration of health risks, cannot afford (or qualify for) group insurance.

The tax bill in the US, which again is not exactly my cup of tea, also matters quite a bit, but taxes are more of an "If you're profitable then how profitable are you really?" sort of concern any any software or infoproducts business which gets to profitability can find a happy outcome for itself pretty much invariantly under any first world tax policy. (Yay for fat, fat margins and big, big markets.)

Aside from the above, there are some month-to-month changes in marketing tactics, what's working on Google these days, how much competition exists in particular niches, but broadly speaking I think not much notably changes from the perspective of someone trying to claw a living out of the Internet. The core problems are still the same: build the thing, find customers for it, convince them to buy. The number of customers is growing rapidly; tools for building the thing get better every year; sales is going to be sales for as long as people are people.

I think that most SaaS businesses are far too solution-focused when they should be more problem-focused, particularly when they're not selling to an expert in the domain who knows precisely what they need out of a tool.

Two which do better at this are https://letsfreckle.com/ (and everything else Amy Hoy does -- if you are reading this, you should certainly have her on your radar) and Basecamp.

If you were to start selling a B2B SaaS tool MVP aimed at inside sales reps, what would you do?

I would start by doing informational interviews with inside sales reps in a particular industry and asking to shadow them doing a Day in the Life if possible, and to ask them to walk me through it if actual shadowing was not possible. I would approach that with the seriousness of an ethnographer who was about to have his funding pulled if he didn't write the best paper ever about the sacred lead qualification process among the modern inside sales culture.

I would look for things which were clearly broken, where lots of human effort was spent doing tasks which added little value, where existing processes dropped the ball (particularly around transitions between people and between systems, because those cracks are frequently where a bit of software spackle creates massive value), etc.

And then I'd tell my confidants "OK, I'm going to build this MVP which will exactly solve this issue that you're tearing your hair out. Are you in?" And if and only if they are in, I would build the MVP. If they say "Well actually that is not my hair-on-fire problem." or "Meh I live with it." or "But Susan does that and I like Susan", then I would find a different problem prior to writing a line of code.