2026 LinkedIn Tips
39 Monday tips posted to LinkedIn in 2026. Newest first. Click any date to open the original post.
September 21, 2026
Happy Monday. If thinking is now cheap, and building is now cheap does that mean the value of the thing you made is cheap too?
Throwing 500 new poorly integrated what if features out just because you can didn't make sense before and it still doesn't. The questions that remain are still the same.
- Does this thing add/create/grow value for my customer in a real and measurable way?
- Is this just new clutter for a one off, tiny segment and it only seems reasonable because of the imagined low cost?
- Is this worth maintaining (even at the imagined low cost which it never is) well into the future?
Just because it's cheap doesn't mean it is worth it.
-jeffhorton
#reddeer #startups #entrepreneurship #smallbusiness
September 14, 2026
Happy Monday. One of the biggest secrets in entrepreneurship is persistence. That you realize thousands of small steps is the only way to get there and all you can do every day is take the next one.
What happens if you take all those steps and still haven't shipped anything or demo'd anything to a possible customer?
Recently talked to someone that is over 5 years into building their idea. Years of research into the science around their problem, dozens of runs down rabbit holes that seem like they might help. Rewritten their software several times.
But they still haven't put it on front of anyone. Any day now they swear they will.
For a customer of one, yourself, this kind of perfection might be worth it. As a commercial venture this is very hard to justify. Your perfect plan never survives contact with the world.
How will they handle feedback that doesn't match their own deeply held thoughts of how it _must_ work? If someone not just dislikes the interface but the very premise they have become emotionally invested in.
This is why we encourage all entrepreneurs to talk to people as much as possible, to get products into room where real conversations happen. I'm not saying the terrible MVP ship until some finds it barely usable, but more direct contact between your product thinking and its buyer.
Good luck making progress today, I hope it isn't year 5 for you still perfecting.
-jeffhorton
#reddeer #entrepreneurship #smallbusiness #startups
September 7, 2026
Happy Monday. Have you outsourced your business thinking to the chatbot? No judgement, we are all trying to get through a massive amount of work every day.
What I hope you are asking yourself is have you stopped being critical, did you stop your own reflection on what you just read. You can get hundreds of pages of text out in a moment but those all require reading and checking just the same as if you had a room of interns make up that answer for you.
Advice that has a built in 'makes mistakes check important info' warning asks more of you not less.
#startups #entrepreneurship #smallbusiness
August 31, 2026
Who is your co-founder? No not them. I don't mean the person that might be on the corporate paperwork. I mean the person (people) in your life that get the emotional rollercoaster job. That stick with you and encourage you not for the big profits but because they know it means something to you to make this happen.
It's often easy to forget about them since they are pretty much always there for you but they are definitely on your ride in real-time. They don't care about your win/loss meetings, your metrics. Only to support your highs and help pick you up from your lows (and maybe a bit of realism).
It might be your parents, great friends, even your kids. None of them are hoping to get rich, that one more sale or one more feature will get them a 100x exit. The people that want that from you have their own motives and while supportive (maybe) they bet on the race. Everyone else bets on you because you did.
-jeffhorton
#startups #entrepreneurship #smallbusiness
August 24, 2026
Happy Monday. Do you know why you started your company? That thing that drives you to make a go of it every single day.
Is it 'saw an opportunity'
How about 'thought I could sell it'
Or even 'Somebody asked for my skill'
Those might be interesting reasons to have on your list but I doubt you chose this path (and stay on it as hard as you do) for these kinds of explanations.
If you look more closely there is probably a thread that runs through your company and probably even back through your jobs. That bit of struggle in the world that you were drawn to because you thought you could fix it, or at least nudge the line forward.
Knowing this about yourself can be a great help on the tough days, or the days with ethical choices and even to help recognize when you are straying away from that core bit of you that made this all possible.
-jeffhorton
#redddeer #startups #entrepreneurship #smallbusiness
August 17, 2026
Happy Monday. Are you taking some moments to enjoy this journey you put yourself on. It may feel like trial by fire but at least its your fire and your trial. You believed in yourself enough to try and here you are, doing it!
Sometimes you can lose track of just how awesome it is, how freeing it is, to be in a place where you are making your own decisions (and suffering your own fates). Think of the alternative, do you miss your badly lit cubicle life?
If you haven't recently, or ever, then celebrate yourself. Not as 'entrepreneur' or 'small business of the year', but as you. 'You' did this, 'You' overcame your fears and doubts and excitements and put your own brain and body in motion to do something amazing.
Celebrate well. You did it.
-jeffhorton
#smallbusiness #startups #entrepreneurship
August 10, 2026
Happy Monday. Do you know your customers constraints? Sure they have the problem, sure it causes pain, sure it costs them money. But something holds them back.
- There could be other unresolved issues they need to, or think they need to, work through first.
- The problem seems so big that even imagining calling you for a demo seems like months of prep and discussion with an already overworked team.
- They have trouble getting other parts of their org on board, it's a 9/10 fire for them but barely ranks against all the other fires everywhere else.
Your work isn't just convincing them you are the right choice. It's helping them with closing those knowledge gaps, allaying those fears, helping your champion(s) tell the story to more people in ways that fit in their workplaces. Your great widget can't even be seen until you help them out of their valleys and that doesn't start from 'book a demo'.
-jeffhorton
#smallbusiness #startups #entrepreneurship
August 3, 2026
Happy Monday. What would a virtuous person do? This is a core question in virtue ethics and it applies to how you operate your business. There are several ways to frame your choices and it can be helpful to think through how your are deciding.
Watching the Westjet strike I'm amazed we are still discussing if some of the working crew should get paid before the airplane doors close. Yes, that is a real thing and certainly seems non virtuous to me.
Another story I saw on reddit was about someone that had their single shift turned into a split shift with 30 min in between to avoid the paid break laws.
It should be reasonable to say that these are not great decisions and exist where people aren't being respected but are seen only as disposable tools. Next time you have a bad experience in the world consider that the worker may not be working for people that respect the ethical frameworks and consider then how you make decisions in your organization too.
-jeffhorton
#startups #entrepreneurship #smallbusiness
July 27, 2026
Happy Monday. Refreshed from the weekend you have a great new idea today and are pumped to get it made and get your team on it. But does it survive the light of day, of explaining it to others?
Founders are great at new ideas, it just takes time and a lot of thinking to bring it to life and if you have existing product figuring out how it fits, if at all.
Before you set the team off in a new bold direction work through a few things to understand the trade-offs you are making
- Is this an expansion that fits with our current customers or a whole new segment and needs a new marketing and outreach strategy.
- If you use your existing team/your own solo founder time what are you giving up to do this. You must be leaving something undone that seemed like the great idea last week.
- What can you do to work your assumptions quickly before you put too many resources into this. It's easy to let others go off and think but you need to be solid on what you are asking them first.
- Didn't you just redo all of marketing last week for your existing product? 😊 You don't even know if that worked and you are already jumping away. Maybe you prefer the excitement of new and need help with the real day to day work as well.
How about you, brand new ideas today?
-jeffhorton
#startups #entrepreneurship #smallbusiness
July 20, 2026
Happy Monday. How many new lines or features did you introduce this year? One, Five, Fifty?
How many of them are being sold or used? Are they all new growing parts of your business or one-offs for a customer that you hope somebody else asks for. Did you build a story around them about achieving customer outcomes and a better future or did they become just another item on a checklist grid of competitor analysis.
It's easy to keep adding on more features and lines and it's hard to grind out new customers and stories and validation but we all know which one grows your business and which one just feels good. All that time building new stuff could have been more detailed conversations and real extensions, better framing, more outreach (and rejection) that would make you stronger.
-jeffhorton
#startups #entrepreneurship #smallbusiness
July 13, 2026
Happy Monday. If your business has a mobile app you are probably familiar with the App Store Tax. That 30% of a transaction that goes to platform instead of your pocket. There are changes now to allow for more off-device purchases but not all of your customers will do that.
Have you started thinking about the AI tax you are baking in to your product and company processes yet?
Right now these AI services are massively subsidized, Silicon Valley style burn cash until your competitors die. You are building them right into the deepest levels of your company at those low-low rates.
Their financial models work if you become stuck and need to spend a sizable chunk on them every month to keep going. Once you have replaced staff or tuned a process just so on a given model it can be very hard to extract yourself or change vendors later and get the same results.
Do you have any plan or at least risk thinking for this yet? When the subsidy ends and your costs double is that still a viable solution?
-jeffhorton
#entrepreneurship #smallbusiness #startups
July 6, 2026
Happy Monday. Have you ever changed yourself for a relationship? They don't really want you, they want someone that bends to their needs.
This is also true for some customers. If you only bent a certain way for them, added some workflows, new features, new direction, just for them then surely they will stay and everything works out.
Changing yourself and your vision for just one person or one customer rarely works and means that you sacrifice your own vision and needs. Maybe out of a desperation, maybe because it feels right in the moment but that customer, like that partner, is going to churn and you will be left holding the bag.
It also means you need to answer what happens to your current friends? Are they confused by this new you? Suddenly you don't fit in with them anymore even thought they showed up for years and got you from day 1?
The risks may be worth it if you really want to go in that new direction but think carefully before you remodel your world for someone.
Is remaking everything worth it?
-jeffhorton
#startups #smallbusiness #entrepreneurship
June 29, 2026
Happy Monday. Do you have a vision for your product or just a wish list of features? It's hard to communicate with your team if the best description you have is arm wavy wishes.
It may not feel like it when you are asking experts to do work for you but for many of them understanding how you see your new idea in the overall experience and customer usage is key to making the best version of what you see. This doesn't mean you need to work every detail with them, but there is a big gap between Steve Jobs obsessive and "I dunno, a form".
Even if you want to empower your team to run with ideas they still need some framework to decide against. Are they clear on the other things we talk about, the customer, the user, the market? And what happens if they come back with the "wrong" thing. What information did you leave out.
Any tips for communicating to your team? Are you the obsessive working every detail or just "the ideas guy" that wants something to sell?
-jeffhorton
#startups #entrepreneurship #smallbusiness
June 22, 2026
Happy Monday. Better, Faster, Cheaper. You know the drill, pick two and hope you pull it off.
What does this mean for your product, that new thing you are trying to get into the world?
- Better. We sometimes say that you at minimum you need to beat a spreadsheet and that isn't far off. Does your new thing fit into the customers life in a way they understand, that they can leverage easily or are you just adding more work.
- Faster. For our new product how quickly can we iterate, can we adapt, can we get those new features out and help the customer move faster by reducing rework and increasing efficiency. Why is that 5 steps, could it be 2?
- Cheaper. It's easy to under price your product but that isn't what we are talking about. Cheaper isn't just the purchase cost. It is the operating cost, availability, training, ongoing issues. If the other product requires an external consultant then straight price isn't the big lever.
A better, faster, cheaper Blockbuster isn't immediately obvious as Netflix but they solved all these issues to create an entirely new category and you know which one survived.
What are you doing to solve this, any tips?
-jeffhorton
#startups #entrepreneurship #smallbusiness
June 15, 2026
Happy Monday. How many assumptions did you test so far this year? You are always making them in your business but have you come up with ways to test them.
You think you need exposure, but do you know which channel really works. Not everywhere, but which one really moves the needle for you. Have you compared them.
You think the product, onboarding, is simple but do you know how much better/worse it works with hand holding. Does white glove mean 10x the usage? Do you have steps you can remove?
How quickly does someone reach the aha moment. It is obvious to you but how long/how many steps before they really see it?
It all makes sense in the moment to you and your team, but what are you doing to test that and see if there is a better path. Not just today but again in a year to see if the usage/understanding has changed.
What are you testing?
-jeffhorton
#startups #entrepreneurship #smallbusiness
June 8, 2026
Get to Know Day: Connecting Alberta's Entrepreneurs to Resources & Growth Opportunities
Are you a startup looking for the right resources to scale, a business owner seeking fresh strategies, or an entrepreneur eager to explore new growth opportunities? Get to Know Day is for you!
The Alberta Regional Innovation Networks (RINs) are coming together to provide an exclusive event for Alberta companies, innovators, and entrepreneurs to network, access key resources, and prepare for the next stage of their business growth. This interactive event will feature presentations from leading innovation organizations and networking opportunities with industry experts. Featuring Presentations From
Canadian Intellectual Property Office (CIPO), Goparity Canada, InceptionU, Alberta's Regional Innovation Networks (RINs) with updates on programs, events like Pitch UP!, EmpowRise and more
https://lnkd.in/gDN8a8dS
June 8, 2026
Happy Monday. Who is your landing page for, you think you will convert someone in that moment, or are you going to give them the page that helps build a case they can use on others?
How many times has your team tried to explore new products only to get stuck trying to get information to even include you on the short list.
Are you hiding your pricing, is it really that special?
Do you talk about the real solves or just buzzwords, synergy!
How does the process work, signup and then ........?
Is your page really only a contact form, are you so bad at explaining you need a sales call to even describe your products?
If someone can't include your page and its content to explain value to their boss then what is it doing for you?
How about you, do you hide details and have shallow landing pages?
-jeffhorton
#startups #entrepreneurship #smallbusiness
June 1, 2026
Happy Monday. Is there a market segment you are ignoring? Perhaps you aren't doing it on purpose, you just never thought of it as a distinct set of customers.
Many years ago I had a friend in sales that noticed this problem. All the services existed for one group but no indicators or marketing outreach to another. Not ignorance, just never thought of it.
Once he pointed this out many of his customers were surprised since of course everyone was welcome to their products, but they had never considered the other personas and how the existing marketing never spoke to them.
This June during Pride Month I ask you, have you considered the other segments and how you talk to them?
-jeffhorton
#smallbusiness #startups #entrepreneurship
May 25, 2026
Happy Monday. Where does your early learning come from? It's great that you got your first few customers but now the digging comes.
What do they tell you about your assumptions on who would sign up? Are they using the product the way you thought? Do you know what triggered them to buy in that moment?
Early customers tell you a lot about what you thought you built and what the market saw. Now you need to figure out if this is the repeatable path or are these customers only half-fitting because you misunderstood the market or you have a miscommunication into the world.
If you can see a pattern, a customer type, an audience, something repeatable then this is a great time to run that book and grow. Now is not the time to argue that customers are holding it wrong or branching out everywhere. Run what wins to grow and then worry about more.
Are you learning from your early customers, did they tell you something you didn't realize?
-jeffhorton
#startups #smallbusiness #entrepreneurship
May 18, 2026
Happy Monday. Last year about this time I asked if you were updating your websites and why. Were you just bored of it? Decided you were Apple and needed big broad language?
The question is still valid, and for those chasing generative search even more important than ever that your site isn't pushing your features but communicates directly to your audience about their needs and how your product enables it.
In your own browsing you know this is true. You don't want another flashy says nothing page. You are in a hurry and need answers about how this product will help you now. And once you signed up are you really demanding a flowery refresh, no, you just want them to make it work and communicate even better.
What do you say? Are you rebuilding all the time or focused on selling the future state, in their words?
-jeffhorton
#startups #smallbusiness #entrepreneurship
May 11, 2026
Happy Monday. "Too expensive" is almost never the real reason a customer cancels. They already saw the price and decided to buy so something changed.
Do you follow up? Do you ask Why they cancelled or what made them cancel. Those are different questions. One is easy to deflect, you do it all the time. The other is about understanding if the customer situation changed, timing is no longer right. Strategies changed. "What" gets you a lot more learning that you can use in the future.
Do you have a flow here or do you just let them drop and never ask anything?
-jeffhorton
#startups #entrepreneurship #smallbusiness
May 4, 2026
Happy Monday!
If you're following up with someone for the third or fourth time and hearing nothing it's probably not you. They may not be "in market" right now.
There's a concept called the 95:5 rule. Only about 5% of your potential buyers are actively looking to buy at any given time. The other 95% might need what you have eventually but not this week. No amount of follow-up emails will change that timeline.
Read about it here: https://lnkd.in/gCDBacit
Instead of chasing cold leads, look for people already showing signs they need what you offer. Someone asking questions in a local group. Someone complaining about a problem you solve. Someone who just started something new. Those are the conversations worth having.
For everyone else, just stay visible. Keep posting, keep showing up, keep being helpful. When they're ready you want to be the name they already know.
-jeffhorton
#reddeer #entrepreneurship #smallbusiness
April 27, 2026
Happy Monday. It's amazing how fast time disappears when interruptions and your regular life pile up. If last week went off the rails then don't think you failed, just pick up a priority and get started this week. Running a business is like your workout, missing a day (or days!) isn't the end.
If you are lucky you learn that that urgent item wasn't so urgent and now you can manage it properly next time. Perhaps with a bit of reflection it becomes clear which things that got last last week in business or life can be delegated or simplified.
As always we are talking marathon, don't feel bad about mile 8 when you know the race has 92 to go.
You have any tips or advice for staying on?
-jeffhorton
#reddeer #startups #entrepreneurship #smallbusiness #alberta
April 20, 2026
Happy Monday.
When you're just starting out it's tempting to keep your product or service broad because you don't want to miss anyone. The opposite is usually what works. Pick a narrow group of people with a specific problem and solve it really well for them first.
That's the difference between a market and a niche. The niche is where you start. The market is where you grow into later. You don't have to stay small forever, but you have to start small on purpose.
This applies whether you're building an app, opening a storefront or freelancing. Figure out who your first ten happy customers would be and go talk to them. Not a survey. Not a social media poll. Actual conversations. Ask what frustrates them, what they've already tried, what they'd pay for. That's your starting point.
#startups #entrepreneurship #smallbusiness
April 13, 2026
Happy Monday. What do you replace, a manual step, a spreadsheet, physical labour, repetitive work?
It's hard for customers to be exited about products that promise results if you put more energy in to them, so what are you doing to take energy out and let the magic happen.
Not needing to go on site saves not just time and money in travel costs but also all that local collection and updates and data aggregation.
Automating reports and insights means less paperwork but also a faster more targeted response before issues get huge.
Turning a few physical steps into a single operation, repeatable and higher quality adds value overall.
Saving time isn't enough, making a customer manage your solution isn't enough. You must save and provide growth value they can leverage to really connect.
-jeffhorton
#startups #smallbusiness #entrepreneurship
April 6, 2026
Happy Monday. So you decided to be a founder. That is awesome and I hope you have an amazing journey.
Let me answer a few questions you have in mind
How long will it take? Longer
How much work is it? More
How many setbacks will I have? Several
Will I feel emotionally stable doing it? Unlikely
Will my friends and family understand? Probably not.
That hardly seems convincing does it.
Let me tell you the other side
Will I feel great knowing I'm doing something on my terms? Yes
Will I learn so much about myself and how far I can go? Yes
When my products connect and really help someone is that an amazing feeling? Yes
Will I regret that I tried? No
Taking the jump is hard. Sticking with it, harder. But it is an amazing thing to try and a lot of fun is had along the way.
-jeffhorton
#smallbusiness #startups #entrepreneurship
March 30, 2026
Happy Monday. Everyone dreams of user generated content for their marketing. Oh how great it would be if customers would make high quality passionate posts on how your product saved them from disaster or provided super hero powers. If only they could build the templates and tools inside your platform so you don't need to.
So what happens if they do it? Are you monitoring your socials to find and amplify and thank them. Does your brand even exist in their world that mentioning it would have any value to them?
What about in product? Have you decided that user provided templates or workflows are dangerous? One offs just for that customer with no way to share?
User content is about taking the magical powers you helped enable and letting your users show them off. To get their own satisfaction (and dopamine buzz) from sharing and hearing that others approve and love what they did too.
Whether reviews and love or templates and tools, what is your strategy to help celebrate them using your brand to achieve that awesome future state you promised?
-jeffhorton
#smallbusiness #startups #entrepreneurship #founders
March 23, 2026
Happy Monday. If you are building right now the hot term you hear is GEO (Generative engine optimization) but what does that mean?
You have been hearing about SEO for years, that your website and content should be well structured, search keyword ready, Google Lighthouse high scoring. All of these things still matter. Don't ignore them.
GEO is the idea that your content should be more conversational, that it describes your products and features and use cases in more natural language that fit how people ask LLMs for advice.
The part I find interesting is that GEO content is surprising to people. That you have been writing so much stuff that apparently wasn't for people to begin with. Perhaps you have noticed how many sites are just lists of features now, from the product point of view, and not from the customer view.
Future outcomes and state are core to the buying experience but often ignored when you are too focused on your own product thinking and your marketing may have gone off track.
What do you think, sure GEO is a new term, but is the content suggested really a new idea?
-jeffhorton
#startups #entrepreneurship #smallbusiness
March 16, 2026
Happy Monday. Do you need to be 'investor ready', spending huge hours on pitch decks, practicing your presentations and finding ways to prove that you too will be a startup unicorn?
Maybe. If that is really the path you want to try. It is a special type of company and strategy to go down that path. You must have a believable path to 10X over and over. That you have a real way and product that could become a good sized player, or big enough to be competition to one, to end up with an exit/IPO/sale that makes your investors happy. Their game is to spread the risk, you are 1 of a dozen investments, most of which lose, why believe you are the one that will win it all back?
What if you just want to build a great business for yourself, your family or community? Then don't worry about pitching to investors, but do make sure you still know your numbers, how your business needs to really work and how you are going to talk to customers. No matter what this work doesn't go away. Your laser focus on the problem stays the same, the long hours, the same.
Raising money may feel easier since you can hire people to do the thinking for you but they aren't always on the same track and now you have a lot more voices on your shoulder with should and could asks (that feel like high pressure advice), and your goals aren't aligned anymore.
What do you think? Is raising and building the VC way always the answer?
-jeffhorton
#startups #entrepreneurship #smallbusiness #founders
March 9, 2026
Happy Monday. What do you know about the problem that your buyers don't? You have seen this hundreds of times, discussed it and analyzed it over and over.
Before you get to pitching your product have you considered chatting with your customer about perspectives to think it through, existing solutions and their tradeoffs, and the perfect world? That your product just happens to fill perfectly :)
Pitching your features right away doesn't help anyone frame the problem or your solution in it. Setup the world as it is and your product as the rainbow. Along the way you might learn your product isn't a good fit for them at all and now you haven't spoiled anyone's time trying to get your product into a bad fit for everyone.
What do you think? Hard pitch first or some positioning and learning?
-jeffhorton
#smallbusiness #startups #entrepreneurship
March 2, 2026
Happy Monday. Are you excited about what you do? Do you think about the possibilities to build and do and create?
What about 5 years from now, or 20?
It is an easy way to be in the early days, that excitement drove you to start and keep going but what about when you get to some grind days where there is just 'work'? If you keep going you can remember why you did this and get back on to thinking up great things to help your customers.
Think of it this way, discovering new lands still meant 6 weeks at sea or crossing that desert. That is part of the work and if you pay attention there is a lot to learn about yourself and the world along the way too. Add that to your progress, don't let it convince you that it isn't worth continuing and exploring and being excited on the other side.
-jeffhorton
#startups #entrepreneurship #smallbusiness
February 23, 2026
Happy Monday. Content Content Content. Get it by the bucket full!!
Are you just filling up space, must publish, must blog, must gate some content to get an email only to shovel more?
The language models have made it even easier to create more faster but are you contributing anything? Are you making stuff that anyone wants to read or might take an action from? It has been advice for a while that you need to post and publish to keep the algorithms happy but much like TikTok, a 1 second impression doesn't really connect even if it is counted as a view.
So what am I suggesting instead? That you remain thoughtful in your creation, that what you publish helps your audience learn from you, respect that your brand knows what it talks about, and help keep you top of mind as a trusted source for the product that solves their problems.
What do you think? Flood the zone or mindful connection?
-jeffhorton
#startups #entrepreneurship #smallbusiness
February 16, 2026
Happy Monday. Do you expect to close every sale? To win every call? If you are doing that, amazing, keep being great! But for the rest of us it's worth remembering that you won't close everyone.
Sales is hard, customer fit is hard. Getting an entire team on the other end of a video call to agree that yours is the right solution can be nearly impossible. So you simply can't win them all and not only should that be understood in your sales goals and projections but also in your emotional preparedness.
The probably didn't reject you the person. Realizing that you can focus on the process, the understanding, the communication and what didn't connect with them. Perhaps it wasn't a good lead, maybe your materials don't talk well to that segment. Knowing that leaves room for learning and growth instead of focusing on the rejection.
Sometimes you can't learn why, you may never know what didn't work.
* The Picard Principle: It Is Possible to Commit No Mistakes and Still Lose.
The point is to keep going and find the next call that will work.
-jeffhorton
#startups #entrepreneurship #smallbusiness #founders
February 9, 2026
Happy Monday. How long have you been working on this? Months, years, decades? I know founders that are disappointed they didn't take the market in month 1 and others that are a decade in and just hitting their stride and some that are 20 years in and still not sure they will make it.
One of the big keys in all of this, just keep going. That day after day persistence in chasing a goal is true in business, sports and any other life goals. This doesn't mean banging your head on the wall for a decade but you don't give up on days it feels uncomfortable, or you happen to wake up in an ocean of self-doubt.
Working those assumptions, getting that inch forward, understanding your own doubts and how to work them out, as true or false, is the daily work of a founder.
Nobody should have told you this was easy, it is a marathon and takes a massive amount of time and energy (physical and mental!).
-jeffhorton
#startups #smallbusiness #entrepreneurship
February 2, 2026
Happy Monday. How long does it take for a customer to get value from your product? Not your imagined 'of course hour 1 day 1' but when they can show it really changed things upstream to bosses, when they start telling peers.
It is common startup advice that you are competing with excel, that you need to at least beat their internal hacked together spreadsheet process that is providing real value to them right now.
Are you a product that takes weeks or months to configure, and then the same again to generate meaningful reports?
Does your customer need to 'hold it right' and look at it in just the right light with your customer service or sales people for the benefits to be noticeable?
Right now immediate value isn't the easiest thing to get to in all situations but you should do the work to ensure that your customer sees the future easily and doesn't need to squint for great outcomes to appear. Real numbers, real evidence both help show it is working and also ensures everyone is still on the right track to get the best value they can. After all, that is why you built it.
-jeffhorton
#startups #entrepreneurship #smallbusiness
January 26, 2026
Happy Monday. Products always expand right? New lines, new features, are the best way forward aren't they?
While this seems an obvious way to grow your business it easily leads you down an unclear path.
- Constantly building the new means your team isn't focused on today, and you may not measure the true return of that work.
- Are you tracking actual usage of your product? 100 uses only touched by 1 customer each?
- Are you measuring profitability from them or just as a whole.
If you find yourself on this path cutting is the last thing on your mind but eventually it becomes necessary. Your marketing materials are unfocused, your use cases aren't clear. The sales team is having 100 different conversations every day. Your team is so busy adding that maintenance and optimizing of your most profitable lines never happens.
Maybe 2026 is the year you focus down on what makes your product great, not the year you add yet another unused feature.
What do you think? Have you cut features and product lines before? Did it help or do you think it was a mis-calculation?
-jeffhorton
#startups #entrepreneurship #smallbusiness
January 19, 2026
Happy Monday. Do you pay for booths at trade shows? Do you send your hyper talkative staff?
I heard this question in a recent video about CES, the biggest consumer electronics show around. The host was mentioning how many booths were just people sitting behind tables ignoring the crowd, or standing in front blocking the view but also somehow not engaging anyone walking by.
I've experienced this too and am always amazed. You spend so much time and effort and money to be at the show and then your people act in the most passive way. Your both workers need to say hi, engage, ask if the viewer knows the product, ask if they have ever thought about the problem space you are in.
Sitting there hoping that customers will opt in and drag your product story out of you is not only lazy it wastes the entire opportunity and the energy you put into it.
What do you think? Have you seen this? Do you do this passive play and think it works?
-jeffhorton
#startups #entrepreneurship #smallbusiness #tradeshows
January 12, 2026
Happy Monday. Do you need to get customers on the phone or "they just don't get it"? Time for a think about what happens in those calls that isn't being communicated in the rest of your marketing and sales.
In those calls are you quieting the skepticism of your ability to deliver? Are you filling in gaps in how risky this feels?
Maybe you are a mimic type and finally start using customer words back to them that you never managed to write down in your copy.
Could you be working through bad positioning and finally clear up what category you really are.
Or maybe you just make promises on the phone that you will struggle to deliver, but at least you closed.
Understanding what really happens in those calls is critical to communicating well before the call, and with those that would never get on the phone, including the rest of the team at your customer.
If recording tools feel intrusive (and don't just rely on the summaries), then you can always bring a quiet partner into the call to listen for you and provide feedback, just like they do in other phone work training.
Getting the messaging right is critical to your success, make sure you understand where it works.
-jeffhorton
#entrepreneurship #smallbusiness #startups
January 5, 2026
Happy Monday. New year, new plan! Have you thought about the next few weeks or months? Not at a "I wish" level but an execution level. Sure you want to grow your business 1000% this year but what does that mean?
You need to close 5 new sales each month? How many leads and new outreach is that?
You need to launch a new feature? Do you have any estimate of the work, did you resource it properly?
Need more customer input? Get it on the schedule, x/customers a week of conversation so you stay in the loop with them.
Maybe you want to push on everything everywhere all at once, while yes that is the life of an entrepreneur, having some plan, some goal with real measures backwards so you know where the start is and what getting it done looks like is amazingly helpful.
I hope you all knock it out of the park in 2026.
-jeffhorton
#startups #entrepreneurship #smallbusiness
Take the next step
Come to a meetup and bring the question it raised. No pitch, no sales.