431: Many Heads, Not Many Hats: The Founder's Identity Crisis

We joke about founders wearing many hats, but that metaphor misses the point. It's not about swapping accessories—it's about growing entirely new heads, each with its own brain that thinks, speaks, and prioritizes differently.

In this episode, I explore why the transition from consulting or agency work to software entrepreneurship is so disorienting, and why the instincts that made you successful before might be the exact things preventing success now.

From the uncomfortable truth about acquisition in low-touch SaaS to the cognitive dissonance of believing in yourself while questioning everything you know, this is about what it really takes to become someone new while staying grounded in who you've always been.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/many-heads-not-many-hats-the-founders-identity-crisis/
The podcast episode: https://tbf.fm/episodes/many-heads-not-many-hats-the-founders-identity-crisis

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

Creators and Guests

Host

Arvid Kahl

Empowering founders with kindness. Building in Public. Sold my SaaS FeedbackPanda for life-changing $ in 2019, now sharing my journey & what I learned.

What is The Bootstrapped Founder?

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.

Arvid: 00:00

Hey. It's Arvid, and this is to Bootstrap Founder. Now we often joke in entrepreneurship about founders having to wear many hats, but I think the metaphor is wrong, at least from my own experience. It's not about swapping hats. It's often about growing entirely new heads, not just the cover of the hat, the head itself.

Arvid: 00:26

A new brain is needed that thinks different and speaks different and prioritizes different. And somehow, these heads are all attached to the same body. It's less of a Mad Hatter situation and more of a Medusa situation, multiple perspectives, multiple personalities, and everything is just trying to navigate a world that treats each one differently. So I was on a consulting call recently, and that's where the idea came from. I got into this topic of focus shifting and dealing with multiple projects.

Arvid: 00:55

The founder I was talking to was struggling with something that I see all the time and have experienced myself. They were migrating from a successful consulting practice into building a software business, and nothing was working the way they expected. The focus was off. The priorities felt wrong. And despite having years of professional success behind them, they felt like they were starting from scratch.

Arvid: 01:17

And maybe even worse because their instincts kept leading them astray. And this is a situation a lot of founders find themselves in. You're coming from a salaried position or from freelance work or maybe you've been running a small agency with a low headcount, something personal, something you've built relationships around, and now you're trying to build a software business. And that is a completely different animal, and nobody tells you. So we'll dive into that today.

Arvid: 01:44

Here now, a quick word from our sponsor, paddle.com. I use them as my merchant of record for all my software businesses. And even though they are all different animals, Paddle serves them well. They take care of all the taxes, the currencies, transactions, updated credit cards, all of that, so I can focus on dealing with my own business. So if you would rather just build your own thing instead of dealing with banks and financial regulators, go check out paddle.com as your merchant of record payment provider.

Arvid: 02:13

Now here's what I've come to understand about this transition that these founders have been experiencing. One of the biggest threats to the success of a new software business is the encumbrance with parts of the old one and I don't just mean like time commitments or scheduling conflicts that happens too but I mean the mental models the assumptions the instincts that served you so well before they might be actively working against you now running or trying to run a SaaS. The very things that made you successful in your previous career could actually be preventing success in this new one. So let's talk about one of the big ones. That's urgency and immediacy.

Arvid: 02:52

It's something that particularly when you work on a low touch, highly automated software as a service business, it comes at a completely different time and in a completely different shape than what you're used to. When you're freelancing or you're consulting and your client has a problem, this tends to be a big issue because it is. Right? It is a real thing. No matter what it is, as long as they don't express a problem, you're doing okay, you're doing alright, but the moment something goes wrong, the urgency and immediacy of these problems is palpable for both parties.

Arvid: 03:20

And it often self amplifies when you interact with a customer because when a client tells you something is wrong, you promise to fix it, you talk with them, and it becomes a high priority and there's back and forth and things kinda either escalate in a good or in a bad way, but urgency causes more urgency. Why? Well, because you have so few clients or at least you tend to if you work in a freelancing position. Retaining any one of them is probably the most important customer success mission that you might have. So when you have five or 10 people paying you a couple thousand dollars a month, acquisition all of a sudden is not even required anymore unless you have churn.

Arvid: 03:58

You can coast, you can breathe, you can focus entirely on serving the people who are already paying you and try to keep them paying. But the moment you try to project this approach onto a Software as a Service business, something that has a quite varied and distributed customer base by design, everything breaks. In SaaS, particularly in low touch, highly automated SaaS, churn is inevitable. Retention is never guaranteed for many reasons and with many factors, most of which are completely outside of your control. People's businesses change, their needs evolve and they get acquired, they pivot, they go under whatever right?

Arvid: 04:34

That makes customer acquisition not something you do when somebody churns but it's a constant act, constant part of your operational presence that needs to be dedicated to that effort. This distinction is often hard for people coming from an agency or from the consulting world to internalize. Acquisition needs to be this permanent funnel that you dedicate significant effort to on a regular basis, a very regular basis, because it's always needed. It always needs to be running like a well oiled system. In low touch businesses, in particular, due to the lack of urgency and immediacy when the product is purchased or sold, you can't wait for a trigger to start looking for new customers it has to happen all the time and here's where it gets even more challenging in the consulting world you likely build your business and your own customer acquisition on your relationships personal network your reputation word-of-mouth from satisfied clients who then become champions for your work and when you need new business you can pick up the phone send a few emails to people who already know you maybe grab lunch with a prospect it's quality over quantity at that point but that playbook does not translate well to low touch SaaS not even close the efforts to get a customer's attention to get them to self sign up and try your product well, those efforts usually go on deaf ears most of the time.

Arvid: 05:56

People are quite hard on products they've never seen before or on companies that they've never had a positive business experience with in the past. You'll find that outreach without the personal network or rather outreach that outgrows the personal network or the established network, it's a completely different beast in many unexpected ways. There's nothing to connect with. Nobody there. Nobody, nothing pre existing.

Arvid: 06:19

The old playbooks, the high touch playbooks, the connection relationship playbooks, they're completely unworkable in this new context. So when you try to go for quality instead of quantity, when you do cold outreach or content marketing or paid advertising the way you used to from the more interconnected world that you were in, maybe a world in which you had more reputation, a world in which you had much better connections and much better understanding of how people purchase than what your software product and its specific new customer base offers, well you find that the things you want don't work. And the things you don't want to do, well those are likely exactly what is required. Who wants to write email templates to start sending cold to thousands of people, thousands of companies in the world? Who wants to write these drafts for blog posts that won't rank for the next three, four, six months?

Arvid: 07:09

Nobody wants to do that. It's not a very enjoyable activity. These tasks, they feel tedious because they are. They feel impersonal because they are not personal at all. And, frankly, beneath the level of sophistication that you might have developed in your career.

Arvid: 07:23

But you might have kind of climbed out of doing this work, but now it's something that you need to do because the long term effects of the systematic scaled outreach are significantly more important than what a quick lunch date or a catch up meeting can provide in a low touch SaaS environment. The irony is that the very activities that feel wrong, that feel like a step backward from your refined relationship based approach are often exactly what moves the needle because they aggregate. And this is where cognitive dissonance comes in. And I want you to really sit with this because I think it's uncomfortable. At the moment you become a founder, you have to strike this super strange balance that is so unusual for humans to strike.

Arvid: 08:07

On the one hand, you're building something completely new that nobody has ever done in exactly this way before. You have to make assumptions. You have to believe in yourself to be right that's the biggest assumption of all and you have to make these assumptions and believe in yourself to a very significant degree without that confidence you'll never ship anything you'll never convince anybody you'll second guess yourself into paralysis you don't want that but on the other hand you also have to assume that all the things you know the things you know to be right from prior jobs the things you read about the things you heard about might not only fail to work for you in this new role in this new circumstance they might actively be preventing success. Because you're instinctively, from experience, in a kind of default mode, deprioritizing the things that need to be done right now. And I think this is what Paul Graham writes about in his essays on things that don't scale.

Arvid: 09:00

Because the scalable stuff, the stuff that does scale, is meant for a different kind of business. On your case, probably a different size or stage of business. You will be able to have those enterprise deals eventually, those conversations, those month long sales cycles for your software company, once you move upstream and get back into the enterprise world, but for your first 100 customers or so, you don't know what's gonna work because if you did, somebody else would know too and they would already have built the business that you're building. In a sense, you have to develop this cognitive dissonance actively and to be able to feel it, to experience it without falling prey to either of the extremes. You don't want to fall into overconfidence, you don't want to be overconfident that what worked until now will always work again, but you also don't want to lose track of the fact that your experience in prior roles has given you insights into customer psychology that you can still apply.

Arvid: 09:53

They might look different now, but learnings, the underlying psychological rules, they're still the same. There's another layer to this, and I want to touch on this because it's market related, and that's a concept that Jeffrey Moore laid out in Crossing the Chasm. Because in all cases, in a new business, you will have to deal with this problem. There's always this chasm between the early adopters of a product and the early majority of adopters of that product. And when you're starting out you'll likely find yourself surrounded by innovators like the technology lovers that want to try out new stuff and those early adopters that are happy to try new things.

Arvid: 10:29

But here's what you need to understand: these people do not function like the later stage majority or the laggards that you might have worked with in your consulting days not even close. In fact the higher your jump off points like the more senior you were at the point when you started building the site business or going into entrepreneurship the harder it will be to understand the reasoning and idiosyncrasies of people who are experiencing their own professional life from a much more early adopter perspective the way things are done the way that things are talked about will be wildly different with these customers and even if you're aiming at enterprise customers eventually their perception of security and safety is different there's something called and commonly expressed as the Linde effect things that have been around for a long time will likely be around for an equally long time in the future and its inversion exists too right things that only have been around for a short while are prone to end up being abandoned or ending quickly in failure and that perception that people have internalized is very hard to fight with a customer in the later majority stage.

Arvid: 11:34

They want proof, they want references, they want to know that you'll be around in five years but an innovator and early adopter they'll likely ignore all of this they'll look at the product they might even be a champion for your product at some point within their organizations and they're going to be fighting against the institutional resistance that is expressed in the Linde effect the way you speak to an innovator a potential champion the way you get an innovator interested in your company is so significantly different from how you talk to a laggard adopter if you're used to selling to established enterprises used to that later majority communication style the phrasings you use there and all of that you might find yourself completely out of sync with the people you're actually able to reach at this point. You're speaking a language they don't respond to you're addressing concerns they don't have and you're missing the things that actually matter to them. So what's the way out of this? Well the way out is by allowing yourself to feel that experimentation is not just an optionality it is a requirement for this stage because you will not know which things will work that worked before so you have to try them and see if results are still possible if you're calibrated right maybe what you need to do is spend a significantly bigger chunk of your time on different kinds of marketing efforts sales efforts product development efforts, documentation efforts, all the things that you might not consider to be the most important ones right now, whatever that might be for you.

Arvid: 12:59

Maybe those activities are actually a lot more aligned with this way forward for the current state that you're in. You just don't know. You always have to remember if you're building something new, the situation is new. The thing you're building is new. The surrounding circumstances might look like the old ones, but they're adjusting to a new presence, the new thing.

Arvid: 13:18

Everything is in flux and your assumptions need to flex with that all this to say when we migrate from one profession to another when we start our businesses on top of our experience in the field maybe the methods that used to work aren't smart to use anymore We should embrace not only the insights of people who have shown us that they've done this before learn from founders who've made the transition successfully that's always a good thing to do but also embrace that uncertainty and new approaches are part of the deal they're not obstacles to success they are the path to it so you're not just switching hats you're growing new heads and new brains and that's uncomfortable it's disorienting it might even feel like you're losing your identity like you're becoming someone you don't recognize but it's also exactly what the situation requires in entrepreneurship and the good news those heads are still attached to the same body I'm stretching the metaphor I know but your experience your judgment, your understanding of people, that foundation is still there. You just need to let it express itself in new ways. And that's it for today. Thank you so much for listening to The Boots and Founder.

Arvid: 14:25

You know, speaking of building intelligence from conversations, if you're a founder or a PR expert on a marketing team, you might be missing critical conversations about a brand, your brand happening right now in podcasts on the internet. That's exactly why I built PodScan. It monitors over 4,000,000 podcasts in real time and alerts you when people talk about you. You can turn all of this unstructured podcast chatter into competitive intelligence. And if you're a founder searching for your next venture, please do check out ideas.podscan.fm where we identify startup opportunities from hundreds of hours of expert discussions in podcasts every single day.

Arvid: 15:04

Build what people are already asking for. So share this with anyone who needs to turn conversations into competitive advantage. You can find me on Twitter and just chat with me there at avid kahl, a r v I d k a h l. So much for listening. Have