Questionable Advice: “People Used To Take Me Seriously. Then I Became A Software Vendor”

I recently got a plaintive text message from my magnificent friend Abby Bangser, asking about a conversation we had several years ago:

“Hey, I’ve got a question for you. A long time ago I remember you talking about what an adjustment it was becoming a vendor, how all of a sudden people would just discard your opinion and your expertise without even listening. And that it was SUPER ANNOYING.

I’m now experiencing something similar. Did you ever find any good reading/listening/watching to help you adjust to being on the vendor side without being either a terrible human or constantly disregarded?”

Oh my.. This brings back memories.

Like Abby, I’ve spent most of my career as an engineer in the trenches. I have also spent a lot of time cheerfully talking smack about software. I’ve never really had anyone question my experience[1] or my authority as an expert, hardened as I was in the flames of a thousand tire fires.

Then I started a software company. And all of a sudden this bullshit starts popping up. Someone brushing me off because I was “selling something”, or dismissing my work like I was fatally compromised. I shrugged it off, but if I stopped to think, it really bothered me. Sometimes I felt like yelling “HEY FUCKERS, I am one of your kind! I’m trying to HELP YOU. Stop making this so hard!” (And sometimes I actually did yell, lol.)

I definitely remember complaining to Abby about being treated differently as a vendor back when I first met her, maybe five years ago? It was all very fresh and raw at the time.

We’ll get to that. First let’s dial the clock back a few more years, so you can fully appreciate the rich irony of my situation.

The first time I encountered “software for sale”

My earliest interaction with software vendors was at Linden Lab. As an infrastructure engineer, most of the software I used had always come from open source land. But somewhere around 2009? 2010? the LL data engineering team began auditioning vendors like Splunk, Greenplum, Vertica, etc for our data warehouse solution, and I tagged along as the sysinfra/ops delegate.

For two full days we sat around this enormous table as vendor after vendor came by to demo and plump their wares, then opened the floor for questions.

One of the very first sales guys did something that pissed me off me. I don’t remember exactly what happened — maybe he was ignoring my questions or talking down to me. (I’m certain I didn’t come across like a seasoned engineering professional; in my mid twenties, face buried in my laptop, probably wearing pajamas and/or pigtails.) But I do remember becoming very irritated, then settling in to a stance of, shall we say, oppositional defiance.

I peppered every sales team aggressively with questions about the operational burden of running their software, their architectural decisions, and how canned or cherry-picked their demos were. Any time they let slip a sign of weakness or betrayed uncertainty, I bore down harder and twisted the knife. I was a royal asshole. My coworkers on the data team found this extremely entertaining, which only egged me on.

What the fuck?? I’m not usually an asshole to strangers.. where did that come from?

What open source culture taught me about sales

I came from open source, where contempt for software vendors was apparently de rigueur. (is it still this way?? it seems like this may have gotten better??) It is fascinating now to look back and realize how much attitude I soaked up before coming face to face with my first software vendor. Some unremarkable truths in my worldview at the time:

1. Vendors are liars
2. They will say anything to get you to buy
3. Open source software is always the safest and best code. (e.g. “many eyes make shallow bugs”)
4. Software written for profit is inherently inferior, suspect and niche, and will ultimately be overtaken and replaced by the inevitable rise of faster, better, more democratic open source solutions
5. Sales teams exist to swindle you. They have all kinds of sneaky tricks and tactics to sway you and trick you into parting with your money, buying things you will regret the next morning.
6. Even listening to sales people is treacherous. Like sirens on the rocks, they create needs that ought never to have existed. You should plug your ears and close your eyes as you pass by their booths to resist their sneaky wiles.
7. Software is costly in order to pay for armies of marketing and sales pros whose job it is to convince you that you need their product, when you don’t.
8. Everyone who works for a software vendor — in ANY role — is shilling for them
9. Engineers and technologists who go work for software vendors have sold their souls, and/or are not skilled enough to hack it writing real (a.k.a consumer facing) software. If you once respected them as engineers, it is a tragedy to see how far the mighty have fallen.

I’m remembering Richard Stallman trailing around behind me, up and down the rows of vendor booths at USENIX in his St IGNUcious robes, silver disk platter halo atop his head, offering (begging?) to lay his hands on my laptop and bless it, to “free it from the demons of proprietary software.” Huh. (Remember THIS song? )

Given all that, it’s not hugely surprising that my first encounter with software vendors devolved into hostile questioning.

(It’s fun to speculate on the origin of some of these beliefs. Like, I bet 4) was heavily influenced by my work on databases, particularly Oracle and MySQL/Postgres. As for 6) and 7), those sound an awful lot like the beauty industry and other products sold to women, don’t they?? )

Behind every software vendor lies a recovering open source zealot(???)

I’ve had many, many experiences since then that slowly helped me dismantle this worldview, brick by brick. Working at places like Facebook made me realize that open source successes like Apache, Haproxy, Nginx etc are exceptions, not the norm; that this model is only viable for certain types of general-purpose infrastructure software; that governance and roadmaps are a huge issue for open source projects too; and that if steady progress is being made, at the end of the day, somewhere somebody is probably paying for it.

I learned that the overwhelming majority of production-quality code was written by somebody who was paid to write it — not by volunteers. I learned about coordination costs and overhead, how expensive it is to organize an army of volunteers, and the pains of decentralized quality control. I learned that you really really want the person who wrote the code to stick around and own it for a long time, and not just on alternate weekends when they don’t have the kids (and they happen to feel like it).

I learned about game theory, and I learned that sales is about relationships. Yes, there are unscrupulous sellers out there, just like there are shady developers, but good sales people don’t want you to walk away feeling tricked or disappointed any more than you want to be tricked or disappointed. They want to exceed your expectations and deliver more value than expected, so you’ll keep coming back. They want you to want more of what they have to offer.

I learned so much from interviewing sales candidates at Honeycomb.[2] Early on, when nobody knew who we were, I began to notice that our sales candidates were obsessed with value. They were constantly trying to puzzle out out how much value Honeycomb actually brought to the companies we were selling to. I was not used to talking or thinking about software in terms of “value”, and initially I found it incredibly offputting.(!!)

Sell unto others as you would have them sell unto you

Ultimately, this was the biggest (if dumbest) lesson of all: I learned that good software has tremendous value. It unlocks value and creates value, it pays enormous ongoing dividends in dollars and productivity, and the people who build it, support it, and bring it to market fully deserve to recoup a slice of the value they created for others.

There was a time when I would have bristled indignantly and said, “we didn’t start honeycomb to make money!” I would have said that the reason we built honeycomb because we knew as engineers what a radical shift it had wrought in how we built and understood software, and we didn’t want to live without it, ever again.

But that’s not quite true. Right from the start, Christine and I were intent on building not just great software, but a great software business. It wasn’t personal wealth we were chasing, it was independence and autonomy — the freedom to build and run a company the way we thought it should be run, shipping software to radically empower other engineers like ourselves.

Guess what you have to do if you care about freedom and autonomy?

Make money.

I also learned, belatedly, that most people who start software companies do so for the same damn reasons Christine and I did… to solve hard problems, share solutions, and help other engineers like ourselves. If all you want to do is get rich, this is a pretty stupid way to do that. Over 90% of startups fail, and even the so-called “success stories” aren’t as predictably lucrative as RSUs. And then there’s the wear and tear on relationships, the loss of social life, the vicissitudes of the financial system, the ever-looming spectre of failure … Startups are brutal, my friend.

Karma is a bitch

None of these are particularly novel insights, but there was a time when they were definitely news to me. It was a pretty big shock to my system when I became a software vendor and found myself sitting on the other side of the table, the freshly minted target of hostile questioning.

These days I am less likely to be cited as an objective expert, and more likely to be quoted in some kind of he said/she said, mindless horserace type of thing. I get to see people on Hacker News dismissing me with the same scornful wave of the hand as I used to use while dismissing others. Karma certainly is a bitch, as they say.

I used to get very bent out of shape by this. “It’s not like I only care because I want to sell you something,” I would hotly protest. “It goes in exactly the opposite direction. I built something because I cared.” I can believe that to be true with all my heart — it may even be true! but that doesn’t change the fact that vested interests can create blind spots, ones I may be unaware of.

And that’s ok! My arguments/my solutions should be sturdy enough to withstand any disclosure of personal interest.

Some people are jerks; I can’t control that. But there are a few things I can do to acknowledge my bias up front, play fair, and just generally be the kind of vendor that I personally respect and prefer to deal with.

Six tricks to make yourself a vendor worth listening to

So here is the list I gave Abby of a few things I do and ways I comport myself to try and be a vendor worth listening to. Or at least the kind of vendor I personally would not object interacting with.

Lead with your bias.
I always try to disclose my own vested interest right up front, sometimes exaggerating for humorous effect. “As a vendor, I’m contractually obligated to say this”, or “Take it for what you will, obviously I have religious convictions here”, or “I’m being paid bags of money to tell you X, but actually Y”, etc. Even if it isn’t directly related to your product pitch. Everyone has biases; I would rather talk to people who are aware of theirs and freely share them..

Avoid cheap shots.
Try to engage with the most powerful arguments for your competitors’ solutions. Don’t waste your time against straw men or slam dunks; go up against whatever ideal scenarios or “steel man” arguments they would muster in their own favor. (I almost never see a vendor do this, and it sucks! Comparing strengths vs strengths results in a way more interesting, relevant and USEFUL discussion for all involved. Audiences and prospects LOVE IT. Both vendors usually come out looking GREAT!)

Be your own toughest critic.
Try to be extra rigorous about identifying the worst use cases and relative weaknesses of your own solution. People love it when you willingly list off your own product shortcomings, or elaborate on where your shit suffers compared to competitors, or the scenarios where other tools are genuinely superior or more cost-effective.

You can still talk shit about software, just not your competitors’ software.
I try not to gratuitously snipe at our competitors. It’s fine to speak at length about technical problems, differentiation and tradeoffs, and to answer specific questions about how your product compares with theirs. But confine your shit talking to categories of software where you don’t have a personal conflict of interest.

Like, I’m not going to get on twitter and take a swipe at a monitoring vendor (anymore ), but I might say rude things about a language, a framework, or a database I have no stake in if I’m feeling punchy. (This particular slice of good advice was handed down to me by Adam Jacob.)

Be generous with your expertise.
If you’ve spent years now going deeeep on a single gnarly technical problem, you might know that solution space more deeply than almost anyone else in the world. (Except your own coworkers, maybe. ) Do you know how many people you can help with that kind of mastery?! Spend some time every day on twitter, email, or slack, answering questions for all comers. A few sentences from you might point someone in the right direction and save them weeks of floundering. That’s a fucking gift.

Give honest advice, whether it serves you or not. Don’t limit your help to paying customers. Make friends all over the industry! Maybe they can’t buy today, but maybe tomorrow they can.

Don’t get high on your own supply.
Any good team knows how hard it is to build a product people love and are willing to pay for. Your competitors deserve your respect. Plenty of companies die off after getting too high on their own hype. And just because you have a “better” product doesn’t mean you’re going to win. It takes your entire go-to-market apparatus to grind out a win. This journey is 1% finished. At most.

In conclusion

The canned demo is something I associate with slimy vendors, its dataset cleverly handcrafted to make their software seem lightning-fast and magical. Conversely, I feel strangely reassured whenever vendors encourage you to give their shit a try on your own production systems. Your production data is way outside of their zone of control. That’s confidence.

Everybody expects you to say hype shit about your own product. I think you actually get more attention, admiration, and respect if you break the mold and say hype shit about your competitors, or criticize your own tool.

You can always be “open source” with your knowledge and expertise, even if you have to run a business with your code.

Charity.

[1] Yes, I know this experience is far from universal; LOTS of people in tech have not felt like their voices are heard or their expertise acknowledged. This happens disproportionately to women and other under-represented groups, but it also happens to plenty of members of the dominant groups. It’s just a really common thing! However that has not really been my experience — or if it has, I haven’t noticed — nor Abby’s, as far as I’m aware.

[2] I have learned SO MUCH from watching the world class sales professionals we have at Honeycomb. Sales is a hard fucking gig, and doing it effectively means drawing from so many deep wells and disciplines — empathy, creativity, business acumen, technical expertise, and so much more. Selling to software engineers in particular means you are often dealing with cocky little shits who look down their noses at you. On behalf of my fellow little shits engineers, I am so sorry..