10 Works Smart Tips from a Serial Entrepreneur
Date : September 24, 2021 By
Before I get into the tips, I think it’s useful to learn a little about the distinction between entrepreneurs and serial entrepreneurs. Both are people who seek out problems worth solving and can focus their efforts on a single idea to make a sustainable business out of nothing. Generally speaking, traditional entrepreneurs don’t have the itch to start something new during or even after their first successful venture. This is partly due to risk aversion in that they don’t want to cause one business to fail at the behest of another. But also because traditional entrepreneurs are more motivated more by the outcome of a successful venture than by the entrepreneurial process itself.
It’s worth pointing out that being a serial entrepreneur is different, but by no means better, than a traditional one. Economically speaking, much more wealth has been created by traditional entrepreneurs than has been by serial ones. Of course, when we hear the term, we think of people like Elon Musk, who have built incredibly successful businesses simultaneously. But then there are those like Mark Zuckerberg, Bill Gates, and Sam Walton (the founder of Walmart) who largely only worked on one successful company for their entire career.
So why is this important, and why should you care about work tips from a serial entrepreneur over a traditional one?
The Serial Entrepreneur’s Unique Work Style
Being a serial entrepreneur can be a bit of a curse and I often find myself wishing I had a full-time cushy job or even running a successful long-lasting company. I realized early on in my career that I was an entrepreneur — I just didn’t see things the same way others did. Sometimes that led me to some impressive discoveries and other times it’s had me sticking my head in a hole from aggravation. But it wasn’t until way later in my career, after having a fairly sizable exit from a software company I co-founded, that I came to embrace and understand the serial nature of my affliction.
You see, before that exit, I had some mild success and a wild failure. I felt like something was out of place. My “I can do a lot” work style was evident in those days but I wasn’t able to focus on the right things at the right time. I was less effective and more frustrated. But a few years after selling, I started to hone my seemingly scattered approach to work. I began to work smarter. I tapped into the chaos of serial entrepreneurship.
I began to be driven less by the financial outcome and more by the satisfaction of being able to do a lot of things. I realized that being a serial entrepreneur meant that I fell in love with creating — with starting things from nothing. I love building products and working with a small team. I’m passionate about testing ideas, dropping them when they fail, building something new, and passing the torch when they work. I love the million little challenges that come in the early days that very few Fortune 100 CEO’s could fathom even dealing with.
In hindsight, I’ve left a lot of money on the table. I’ve left companies too early. I’ve given up too much equity. I’ve taken too little equity. I’ve done plenty of wrong things to line my pocketbook more. That’s a bummer. But I can also look back and say I’m relieved to not have 100 people working for me like I once did. I was bored in that role. I had amazing specialists to do everything that I wanted to do and each one of them did their specific part better than I could. When I finally accepted that it was ok to like what I liked, I started feeling normal. And over the years, enduring moderate failures and achieving relative wins, I started relying on certain approaches to work that let me scale my efforts. I developed tools, and processes, and philosophies that enabled me to do a lot of different things and not get too overwhelmed. And most of all, I was happy.
A quick caveat, then on to the tips. Being a serial entrepreneur doesn’t mean being broke. I get that a lot of readers want to make money and enjoy the freedom that comes with financial success. So to set you at ease on this, I’ll just say that while I’ve not made a billion dollars building companies over the past 25 years, I have made many millions of dollars. And I say this not to feed my ego, God knows I could have made a lot more. This is just to say that I’ve been able to achieve significant financial freedom while still doing what I’m best suited for rather than what’s best suited for my bank account.
#1 — Focus on one thing at a time
It’s true, I just told you I can’t focus on just one thing. I have to go from this to that to be happy. But that doesn’t mean I have to do them at the same time. This applies to the big stuff like starting a new business and the small stuff like writing an article. The more disciplined I am at doing one thing at a time the better the result. Truth be told it’s not something I’ve mastered. Though it is something I’m unquestionably conscious of and regularly reflect on. As a serial entrepreneur, you’ll need to be proficient at moving between projects; it can get pretty manic and that leads to exhaustion. Sometimes you’ll have little choice in the matter. Maybe you need the income or you’ve made too many commitments. Or perhaps you are just excited. That’s all ok, the key is to develop a process to check in with yourself. When your process isn’t working for you and you’re feeling overwhelmed it’s time to pare back and focus on less for a while.
#2 — Maintain a well-stocked toolbox
As a software guy, I use a lot of tools. I’ve been asked on a dozen occasions to be the center of software case studies for those I use regularly. This is because when a tool works for me I’m all in. I become an evangelist, telling everyone around me what I get out of using it and why they so desperately need to use it too. And I’m real noisy about it too — submitting feedback, making feature requests, writing articles about missing functionality, and more. And it works. My ideas for what one software product needs to build are frequently bumped to the top of their product roadmap.
So what tools? Each entrepreneur should stock a toolbox with the unique software that suits their process, but there are some that just about every business professional should be using. Right now it’s Slack for communication, Dropbox for files, Notion for notes, Markup Hero for screenshots and annotations, Respona for marketing, Intercom for customer support, Ghost for blogging, Frase for research and Shift for Google Accounts (oh man, I have way too many of those). The point is not to just use what I use, although you’ll probably want to, it’s to spend the time to find the right tools that work for you. Never feel bad about spending 3 hours searching for the perfect clipboard app (yeh, I did that last night).
#3 — Be a generalist and enthusiast
One of the great skills of a serial entrepreneur is being good at a lot of things but an expert at none. This is incredibly useful when starting a new business because you can do a lot of things yourself. In my case, I’m good at marketing, product management, sales, fundraising, recruiting, and I even taught myself to code. But I’m by no stretch of the imagination a rockstar at any of those things. In the early days of a startup, being good at marketing is enough to get the ball rolling. Because marketing is such a nuanced skill, being “good” at just about every aspect of the role, as I am, is essential because you can’t simply a singular marketing discipline and run with that. You have to test everything — from cold calling to paid search and content creation to email outreach, when you’re in a startup may be only one of those tactics works. Later, after you’ve grown a bit, you can hire an email marketing specialist if you determine that’s an effective approach for your business.
Also, be an enthusiast. An enthusiast is someone that gets ridiculously interested in things. Serial entrepreneurs often find themselves hacking late into the night trying to learn a new skill or exploring an interesting topic. Being an enthusiast is the fuel to become a generalist. Enthusiasts are rarely experts at any one thing, but they have a knack for quickly learning the basics of something. This is useful in business partly for the reasons mentioned above, you can just do a lot yourself, but also because you’ll be able to speak the language of many more things. I don’t mean that literally — you don’t need to learn more languages, although that wouldn’t hurt, but rather I mean in a way that keeps you in the conversation whether it’s a technical discussion, a marketing one, or a product dialog
#4 — Have a thick skin and embrace uncertainty
Be ready for resistance. Man, I’ve lost my sh** a few times battling in board meetings. But it’s not about being combative or inflexible. For me, it’s about putting it out there. When I have an idea I’m not afraid to share it — I used to be, but not now because as aggravating it is when people don’t “hear” me, it takes rarely more than a day to realize it’s not personal. My dad has a great saying. “I care, but not that much”. For him, it’s never getting too attached to anything, and that’s good advice too, although it didn’t make my top ten. But I always interpreted his quote as not caring enough about what other people say or do or think to lose more than one night of sleep over it. That works for me.
When you share your ideas, some people may just not see it, whereas others might think it’s dead wrong, but an unshared idea is never heard.
#5 — Be a prolific writer
I didn’t get very good grades in high school. And English was my worst subject. Ironically, I ended up an English major in college — that’s another story for another time. What’s important is that at some point I learned how to communicate my ideas on paper. I probably absorbed a lot more in high school than my grades reflected, but by the time I started my career, I was a pretty darn good writer. I’ve found that good writing is the single most valuable skill for an entrepreneur or business professional. And being a good writer is not limited to long-form content like books, white papers, or even blog posts. Think of all the things you have to write daily: emails, text messages, presentations, proposals, sales pitches, investor decks, product requirements, job descriptions, and a hundred more things. All of these forms have one thing in common — that is you are trying to explain something that’s in your head.
One of the tricks I use is starting with outlines. I keep the formatting simple, just numbered or bulleted with indents. I frequently find myself creating a 1-page outline before setting out to write a blog post or presentation and even emails sometimes. This practice saves me a ton of time because I can get the core ideas down in front of me which allows for two important things that can be missed if I just start writing paragraphs. Those are:
- Ordering the Ideas – mixing and matching thoughts until they tell the story in the right order.
- Scan for Mission Points – quickly looking through my outline to see if I’ve missed anything critical.
Writing, versus speaking, gives me much more control of the words. I can take the time to organize and position thoughts before they are ingested by other people. That’s not to say learning public speaking isn’t useful or important, I certainly had to get comfortable with that skill to teach entrepreneurship for 10+ years. But I would take effective written communication over public speaking in a heartbeat.
Any great novelist will tell you that being a good writer takes practice, a lot. So be prolific. Get your ideas out of your head and onto the screen (or paper if you still do that).
#6 — Articulate your words clearly
To my point in #5 about public speaking, here is the most important aspect of being a good presenter. Whether in person, live on stage, on a recorded webinar, a Zoom meeting, and even on the phone, the key is to articulate your words. In today’s business environment we are interacting with all kinds of people from all parts of the world. Not everyone speaks English as a first language. And even for those that are native speakers, people tend to hear only 2-3 words in every 5-7 you speak. That means you need to emphasize and articulate the important ones so people truly “hear” you.
I’ve developed a few tricks when I’m speaking to a colleague or business professional. First, I regularly adjust my cadence. By that I mean sometimes I speed up whereas other times I slow down. I do this to keep the listener engaged and I often use this technique to grab the users’ attention to important parts of what I’m saying. Next, I try to repeat important aspects of my talk, but I don’t simply say the same thing twice. I find a way to restate the same point either from a different perspective or with another example.
This approach helps the listener see that what I’m saying is worth hearing and I give them multiple ways to internalize the information. Finally, I like to use pause frequently while I’m explaining myself. This gives me a moment to let my brain catch up with my mouth. Similarly, it gives my audience a chance to connect with the information they just heard before I go on to the next point.
Like writing, speaking takes practice. Be deliberate when you’re talking to people. By that, I mean plan to practice these skills before you start a conversation or speech. If you wait to the end to see if you did it right, you probably didn’t.
#7 — Look for problems, not solutions
Here’s a favorite of startup entrepreneurs. Human beings naturally try to jump create solutions — we’re hard-wired for that it seems. And that’s a great skill, but solving a problem that nobody thinks is a problem is nearly a waste of time. And often that’s the easy part. I’ve told my students no less than 1000 times to stop solving and start understanding problems. The most successful entrepreneurs look at the world through what I like to call the “problem lens”. The problem lens is a way of seeing problems in our everyday life. That isn’t to say that entrepreneurs are cynical or pessimistic, the exact opposite.
The idea is to look for problems as opportunities. And this isn’t limited to coming up with a startup idea. I look for problems as opportunities in my daily activities — sending emails, creating blog posts, writing proposals — when I keep a keen eye out for problems I’m able to better accomplish my goals because I am less likely to overlook something important. Or worse, people can’t understand what I’m trying to do or communicate.
Business professionals often use tools like the business model canvas made famous by Eric Ries and the lean startup movement to get a picture of where problems occur in their companies. But I find that just remembering to put on my problem lens before I start the day makes a big difference in my work product.
#8 — Don’t be afraid of bad news
Ugh, this one is so tough. I hate bad news, so much so I’ll do anything to avoid it. But that’s not a good habit. I’ve had to train myself to think of bad news as good news, which it turns out is often the case. Good news is, well, good, so there isn’t much action we can take on it. We’re left happy and feeling fulfilled when we hear good news — whether in business or life in general. Contrary to good news, bad news is entirely actionable. Knowing that something isn’t working or that something didn’t resonate gives us insights into what could make it work. That’s powerful. So in more ways than one, bad news is way better than good news because we have next steps to take.
So even though it hurts me to hear bad news, I’ve realized it’s the only way for me to progress in business. I can’t say I’m happy to hear it just yet, but I can get over the initial sting and look for the opportunities that bad news creates.
#9 — Be gracefully wrong
Like good news, being right is also a dead end. Sure, it feels great to be right and everyone wants that. But when we’re right, then we’re done. Being wrong on the other hand creates opportunities for us and the people around us. The trick is to be gracefully wrong. By that I mean two things. First, I have to put myself out there with the understanding that I might be wrong, or at least other people might think I’m wrong. This takes some courage. Moreover, when I am wrong, I can’t take it personally or get upset. I have to handle being wrong with grace and dignity.
In fact, for those that can’t be gracefully wrong something really bad happens. They end up surrounding themselves with “yes” men. These are people that aren’t willing or comfortable to tell you you’re wrong; instead, they say you’re right even when they know you aren’t. This is a disaster because you’ll end up making terrible decisions. We need people on our team that are comfortable having differences of opinion. It’s this conflicting dialog that leads to the best solutions. But when you’re able to see your own mistakes and acknowledge them, people will do that in return and you’ll have the space to share ideas openly and freely.
#10 — Don’t give up, but do let go
Giving up and letting go is not the same thing. Our parents often told us to never give up. In business, most successful entrepreneurs will tell you the same thing. But understanding the nuances between giving up and letting go can be powerful. Giving up is something we do when we’ve lost all hope. It’s the “end of the road”. Giving up is painful and discouraging.
Letting go is completely different. This means we are separating from the outcome either by walking away from something that isn’t working or conceding to another path or line of thinking. In many ways, it’s the opposite of giving up. When we “let go” we’re accomplishing two things. First, we acknowledge that something isn’t working and become willing to see another path. And second, we’re creating space for us to get motivated by the alternative path. When we give up, there is no alternative path. It’s just over.
Wrapping Up
So that’s my 10 tips as a serial entrepreneur. I know these tips work, from my own experience and that of hundreds of entrepreneurs I’ve worked with over two decades. And they’re straightforward enough that anyone can put them into practice today. Like everything in business, take what works and leave the rest. There is no one path to success. I’ve always found that some things work, some things don’t and some things work sometimes. The key is to practice and develop a system that works for your unique personality.
Good luck out there!