Welcome to the thirty-sixth edition of The Baton. A fortnightly newsletter that brings you three, hand-curated pieces of advice drawn from the thoughtful founder-to-founder exchanges and interviews taking place on Relay and the interwebz. So, stay tuned!Â
As the year-long chorus of highs and lows, both strange and familiar, gets blown into these closing weeks uninvited and demands necessary pause, we hope this last edition serves a worthy companion!
Drawn from the newsletterâs archives, here are five founders looking inward, reaching for the differences between âpersistence and idiocy,â interrogating âstartup BS,â revisiting âhustle,â and being âdeliberate in examining their own strengths and weaknesses.â Tender, introspective missives for this in-between time. :))
#1: Managing a persistently baffling founder dynamic â mmhmmâs (formerly Evernoteâs) co-founder and CEO, Phil Libin, on an essential method of truth-telling he has long adhered to; âdealing with: âYouâre going to be the first person to know and youâre going to be the last person to admit it.â â (Source: The Accidental Creative)
I got this advice as a CEO at Evernote. A while ago. And this was from one of our investors. I think it was from Henry Ellenbogen⊠This is amazing. Iâve given this advice a lot and I follow it all the time. He said, being the founder and CEO, youâre going to be the first person to know when something is really wrong. Youâre going to be the first person to sense, âlook, this isnât going right.â Something bad is happening. Company isnât doing what I think it should be doing.Â
Youâre going to be the first person to know and youâre going to be the last person to admit it. Which is a brilliant formulation, right? You have your fingers everywhere. You have more information than anyone else. You just need to have a feel for it. Youâre going to be the first person to know when something is wrong. But as you also have the most invested, youâre going to be the last person to actually admit it.
So what you have to do is, be aware of that and then try to defeat it. How do you use the superpower, being the first person to know and mitigate the fact that youâre not going to admit it to yourself because you have so much at stake.Â
He suggested a process which I still do with every project. Which is:Â
Find a time when youâre in a pretty good mood. You donât want to do this when youâre frustrated.Â
Just write down and you donât have to share it with anyone, just write it down for yourself.Â
What do you want to accomplish in the next six months or twelve months, whatever time frame, you want, that if you accomplish it in that time period, youâre going to be like, âyup, weâre doing great, things are going according to plan.â
And if you donât accomplish it, youâre going to be like, âoh something is seriously wrongâ Decide that, write it down, you can share it if you want. I usually donâtâŠ
And then just put it aside. Then, look at it, when times are tough in six months.
Both ways work really well. Sometimes, six months go by and you actually feel like crap. And you look at this thing and youâre like, âoh, wow, we did all of that stuff.â Itâs hard to acknowledge because in the day-to-day, you focus so much on whatâs going wrong. But actually, look, six months ago, I said that Iâd be super happy if we accomplished these things and weâve done it.â You need to be super happy.
Thatâs actually really useful.
Or sometimes youâre pretending that things are great. But you look at this and see, well, six months ago, you said, weâll have to do these things but weâve not done any of them. Why do I still feel good? Am I just lying to myself?Â
That kind of conversation. Overcoming the founder dynamic of, doubling down on being the first person to know when something is wrong but defeating the âbeing the last person to admit itâ has been super powerful.
#2: The difference between persistence and idiocy â EnjoyHQâs co-founder and CEO, Sofia Quintero, on the many paradoxes and unknowns of being a founder and how one must come to terms with them. (Source: Relay)
If I have to give any advice to anybody who wants to start a software as a service business, this would be:
Try not to raise money from traditional VCs. Plenty of new alternatives are available out there.
Be an example for your team. Do not expect anything from anybody that you are not willing to give yourself.
Find a therapist or coach, probably both if you can afford it. Your mind and emotions will be the biggest challengeânot the business.
Learn how to talk to customers. Itâs not enough to talk to them, though; you need to know what to ask and how to interpret what they say. Make the best of each conversation. Listen, and forget about your ego.
If you are not technical, as in being able to code, learn how the sausage is made. You will have much better conversations and the ability to lead product development efforts more effectively.
Try a lot of things quickly, but donât be reckless. This one is hard. You will understand the balance with time.
Try to understand the difference between persistence and idiocy. I still donât know it.
Be good to people; your reputation and relationships will survive beyond your business.
Donât lie to yourself. Pursue the facts with optimism.
Unfortunately, most stereotypes about lawyers and accountants are true. Find good people who understand your space, and constantly remind them that you need them to translate what they do in plain English so that you can make better decisions.
Related to the above, if you donât understand something, ask as many times as needed. Looking stupid is better than being stupid.
#3: The dangers of startup BS â Geckoboardâs founder and CEO, Paul Joyce, urges founders to exchange sincere realities, the feats and foibles of their respective journeys. (Source: Relay)
As founders our job is to manifest something that exists only as an idea, into something real.
This is no mean feat and can be incredibly challenging.
Part of this is necessarily convincing yourself that it is possibleâŠ
That requires inspiration, research and just a sprinkle of delusional thinking :)
The problem comes when we do this without sensitivity and project it outward.
In particular, when we layer in lies of omission (crowing about the good stuff but leaving out the stuff that makes us feel like crap).
This is damaging to ourselves and our business when itâs an internal dialogue.
But has collateral damage on other founders who hear that one-sided story from their peers and are left feeling like theyâre the only ones suffering.
Thatâs why communities like this, be they virtual or face-to-face, that allow founders to drop the filter and talk about some of the pain are really important.
One simple thing that we can all do when asked about how weâre doing by another founder is to present a balanced view.
Instead of saying: âWeâre doing great! Just launched a new feature and closed a Series A with investors x.â You could try: âWe just closed a large series A which Iâm delighted about. But Iâm struggling with how Iâm going to meet the expectations of our team and investors.â Or: âWe landed marquee client y but lost a couple of valuable customers that has caused me some concern.â
Iâve found this opens up conversations, is a great way of building mutual trust which can even lead you to a discussion that can help with those pressing concerns (there are always pressing concerns).
#4: Revisiting founder hustle â Wildbitâs co-founder and CEO, Natalie Nagele, having been at it for almost two decades, reflects on and implores fellow founders to revisit the ever-divisive idea of âhustle.â (Source: Wildbit)
These businesses weâre building have cycles when they need us to hustle, and when they can afford for us to live a more peaceful existence. Even in a stable, successful business like ours, we have times where we have to give up more of our time away from work to get something out, to get ourselves out of a jam, or to support our team in the work that theyâre doing. Just like when you have to jump in and help a grown kid, sometimes the business needs more from you. But the badge of honor is not on working long hours, itâs instead accepting that youâre available when itâs necessary, but fighting for those times to be exceptions and not rules.
I want new entrepreneurs to not feel guilty or wrong for working hard at something they are crazy passionate about. Your business will pull you in and occupy your every brain cell. You will be excited about it, worried about it, passionate about it. Channel that towards getting to a better place. Find the important things to work on. Remember to find time for your health, mental, and physical. Make some friends with founders who have been there before and see the other side. Maybe they can suggest a workaround or just trigger a gentle reminder to get outside. But donât feel guilty about it. Weâve all been there and are only so dogmatic because weâve seen the other side.
#5: The caveats to consider before you hire to âbolster your weaknessesâ â SparkToroâs co-founder and CEO, Rand Fishkin, eloquently urges founders âto be prescriptive and deliberate in examining your own strengths and weaknesses.â (Source: Lost and Founder)
The conventional wisdom that you should bolster your weaknesses with great hires who can give you that strength isnât totally wrong, but every time this advice is passed on, it should contain these three caveats:
Lacking deep knowledge and understanding of an area means that you are less likely to have connections in that field, less likely to identify right versus wrong hires in that field, and less likely to successfully recruit and convince great talent to join. You might not even realize which knowledge you lack (unknown unknowns, amirite?).
A founderâs weaknesses are often baked into the companyâs DNA and create a figurative kind of debt (nonideal practices or systems) that must be addressed before progress can be made. If you lack engineering skills, this often manifests as technical debt that must be remedied through re-architecting and rebuilding core systems before adding features or enabling scalability. If you lack people management skills, itâs likely organizational debt that requires months of digging into interpersonal and intra-team conflicts, letting go of some staff, rehiring, and creating processes for engagement and teamwork that build trust.
When you rely on someone (or several someones) to bolster a weakness, their departure from the organization creates risk that the wound will reopen. This risk is greater in smaller and less-experienced teams where the senior leader is often the glue keeping things together with their presence, and lessens as organizations grow (so long as that leader has created consistent quality through redundancy of great people and great processes).
Hiring or finding a skilled cofounder is not the only way to bolster a weakness.
If you have great confidence (or considerable fear) that an area of weakness could be your companyâs downfall, you can invest in that attribute. But first, you have to know it exists.
That process is eminently achievable, but few entrepreneurs have the self-awareness or take the time to diagnose. Iâve fallen prey to this too many times. My advice, therefore, is to be prescriptive and deliberate in examining your own strengths and weaknesses. They will, almost always, map shockingly well to those of your companyâs.
Until next year,