20 Tips & Tools That Helped Me Become (And Grow As) A Serial Entrepreneur

In the reflections I’ve been sharing over the past few months I’ve focused a lot on what we’ve been doing at the organizational level at Kimp. And I’ve gotten into a bit of how we’ve grown and transitioned between business models, and throughout the pandemic. But as many of you know, as an entrepreneur what you do at the organizational level is only part of the equation. A big, important part of the equation, yes. But none of that can be implemented or optimized if how you operate as an entrepreneur is all over the place.

Below are a few of the tools that I’ve come to rely on the most over the years that I’ve been a serial entrepreneur. And why I’ve found them to be particularly helpful. Check out the list, take what may help you on your way, and please share any suggestions/alternatives you’re finding to be game changers.?

Project Management?

From my days as a solopreneur, designing banner ads, to present day with KIMP, which involves a larger client base, project management software has been crucial. If your operations are in early stages, don’t think that you don’t need it yet. The sooner you invest in tools that help keep you organized, and running in systematic ways, the better off your growth trajectory will be.?

And for organizations that are a bit further along - don’t be afraid to shop around if your current software isn’t quite doing all you need it to. It’s a bit painful to migrate your team from a software that they’re used to and love. But it is much more painful to continue with one that is limiting your potential or creating inefficiencies. Below are a few of the tools I’ve used over the years:

ActiveCollab, back in 2005/2006. At the time the software had to be purchased and hosted on your own server, which meant that you were in charge of making sure updates were done manually. It’s come a long way since, having helped over 50 000 teams according to their site. Back in the early 2000s it was just a good start and not quite robust enough when it came to features to handle all that I needed it to. But today it looks like a project management software worth giving a second glance.

Basecamp (designed, built and backed by 37Signals), is a solid project management software, run by a great team, and to date still has a competitive list of features and integrations. I loved Basecamp so much after first signing up for it that I actually convinced a few clients to sign up for it as well. For simple, linear workflows, this is a great software.

Trello, with its Kanban view, is hard to beat when it comes to working on projects that include multiple steps or stages. It gives everyone collaborating on the project a birds-eye-view of what’s going on. And for that reason it became the Project Management software that we used to launch KIMP with.????

While we eventually worked toward building our own project management software at KIMP, to meet the unique needs that we had, we built on a lot of the great features that we used in Basecamp and Trello in particular.??

Documentation?

Google Workspace (previously G Suite), is hard to beat when it comes to having all of the tools in one place that allow for an entrepreneur to document and build on their plans. Since early on the simplicity of the interfaces and features have made it very easy to collaborate on. And with the amount of investment Google has been putting into integrating AI into its products you can be sure that the user experience is only going to get better.?

Notion is another option I’ve explored for documentation and that we’re currently using at KIMP. If you’ve got processes, and communications, that you need to organize and make more accessible, Notion’s a tool worth checking out. Especially when working remotely, and communicating ideas through pages and pages of text. Notion helps clean up that clutter by streamlining everything into easy-to-navigate sections/steps.

The Home Office Setup?

Now these aren’t exactly the tools that you’ll think of coming across in a list of mostly software. But as an entrepreneur you spend long hours sitting at a computer. And you need to make sure that your setup is setting you up to last through all of that.?

From a MacBook fan to a Chromebook convert - As a designer, and then for many years afterwards as I took on the reins of running a business, I loved working on a Mac. You couldn’t have convinced me otherwise. But during the pandemic I discovered how far Chromebooks had come, and as someone who loves and relies on Google Workspace heavily, it was a no-brainer to make the switch in 2020. These days you can get a lightweight device, with a decent display and a competitive price tag. AND best of all - you’re not tied to what’s saved on the machine. Since you’ve got everything synced up with your Google account, through the native integration, if anything should happen to one device, you can just move on to the next.

Invest in ergonomic elements - It’s a lot to buy everything for your workspace with ergonomics in mind. But 2 things you won’t go wrong with are a solid chair and a great mouse. For the chair, you can shop around. Marketplaces can be a great place to scoop up one that’s gently used. Or spring for one that’s on sale. Trust me, your back will thank you. And for the mouse, I’d recommend the Logitech MX Master. It’s a wireless mouse with a great battery life, and it lasts forever.

Productivity ??

Todoist - The Kanban view and clean UI is what sealed the deal for me with this app. I love any app that is as well-designed as Todoist is. In this one, you can set up different to-do lists for different areas of your work/life. And then you can create stages for each i.e. “To Do” “In Progress” “Completed”. Being able to see everything, and where it’s at, at a glance helps me to stay on top of things. I also like the fact that I can invite others to collaborate on specific lists.?

Content?

Spotify - My go-to app for educational and motivational podcasts. You just can’t beat it for quantity and quality when it comes to audio content. And when you’re stuck in traffic or doing something hands-on, being able to quickly throw on some content that can help ground you or contribute to your growth, goes a long way.

Kuku FM- Another platform for great audio content that I more recently discovered is KuKu FM. Based in India, Kuku FM serves up content spanning 50 genres and 7 languages. With Tamil being my first language, it’s a great feeling to be able to take in content in Tamil that’s been translated without losing the intended meanings and nuances. Kuku FM has opened up a really nice way to explore books related to marketing and business in general, in languages other than English.

LinkedIn, Facebook and Instagram - Across social media, I try to be really careful about only engaging with content that I want to see more of. To keep the algorithm on my side, I avoid opening links others share with me unless I’m sure that it’s related to motivation, travel, marketing or AI. And if I do happen to click on something, I try to hide that kind of content soon after to avoid more of it.

With Instagram, I’ve taken advantage of the collections feature and I’ve found that really helpful in being able to curate collections of content that I can go back to when I have the time to review it in more detail. And to avoid too much time on the platform, I’ve set up the in-app timer.

Business Inspiration/Innovation

When you’re an entrepreneur it’s easy to get hyper-focused on your own business model and unfortunately miss out on new opportunities. That’s why I’ve found that following sites/platforms that feature up-and-coming startups to be a great source of inspiration. Here are few:

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Acquire.com is a marketplace for startup acquisition. And it’s a great place to keep your finger on the pulse of what other entrepreneurs are building and shipping. By keeping an eye out on what people have launched, and the value they’re seeking when they’re trying to sell, you can get a good sense of what the demand is for different types of products/services. And you may just stumble onto an idea you can integrate into your existing operations. Or you may come across a business you’d like to buy.

Appsumo is a great marketplace to discover and/or buy products that can help you grow your business. I love it because you get opportunities to purchase lifetime access to up-and-coming software. That means a one time fee and ongoing access to a wide range of tools. Everything from AI tools to productivity tools to things you’ll need for marketing and operations. All at very accessible rates for businesses of any size.??

Product Hunt is a platform on which entrepreneurs are regularly launching, and providing feedback on mobile apps, websites, hardware projects, and tech creations. It’s a great space to see what others are building, keep up with new tech and see how it’s being received as well. You can get to know what’s popular, as well as pain points and gaps in current offerings by taking a look at what’s been launched on Product Hunt.?

HouseSigma isn’t a site that’s necessarily going to provide inspiration for everyone on their next big thing. But I’ll explain why I’ve included it here. It’s a site that entered an established market and disrupted what was already being done by offering up something new -? free automated home valuation for real estate listings as well as historical sold information. With an eye on Real Estate Tech as the next space I’d like to launch a venture in, keeping up with sites like House Sigma which are at the forefront of this is key. So whatever your next big thing is - identify a frontrunner. And keep up with how they’re operating/engaging with their audience. It’ll help you start to establish a framework and roadmap for your own path.

Keeping Up With AI

Midjourney - Across the many text-to-image generators, Midjourney continues to reign supreme when it comes to the type of aesthetics it delivers. I regularly check out tutorials and play around with prompts and shortcuts to see what the capabilities of the latest iteration of Midjourney are. Text-to-image generators have a ton of capacity to transform how we design and imagine creatives. And getting to know the tools first hand goes a long way in figuring out how to roll them out to customers to offer new solutions and solve different pain points.

ChatGPT - ChatGPT is probably one of the most interesting AI tools to have been rolled out publicly this year. New use cases for it are constantly being discovered and shared. And it’s incredibly fun to submit prompts to see just how much you can automate.

Getting Healthier

Software aside, a few of the key components to keeping me sane and energized are eating well, drinking lots of water and getting workouts in. No doubt there are times that work and life get busy, but to keep going as best I can I’ve found the Fittr app to be especially helpful:

Fittr - This has to be one of my favourite fitness apps to date. It goes far beyond just how-to content. There are tools and tons of well-researched information that help you set and achieve your fitness goals. And there’s a community built around the app, giving users the opportunity to connect with and gain inspiration from others.

Travel Hacks

Over the past 20 years I’ve been on more trips than I can count, from trying to build business partnerships, to exploring new markets and hiring team members. Here are a couple of sites that have saved me time and money and have made long-haul flights a lot better:

ExpertFlyer - This tool is great for helping flyers get more value out of their bookings. With info like available seats on flights, it’s a subscription that’s well worth the cost ($4.99/month for basic, or $9.99/month for premium).

Straight To The Points - This site allows you to keep up with the latest updates from airline and hotel loyalty programs as well as flight prices. Deals on business class seats anyone? With as much fluctuation as we’ve seen since the pandemic, this resource has been especially helpful to navigate it all.

And that’s it for some of my favourite tools that have helped me on my journey as a serial entrepreneur. If you have any questions - or suggestions - please feel free to reach out!