Ian Wiedenman blog

I grew my company ITW Creative Works from a start-up to a thriving creative development agency through strategic business growth and strong client relationships.

Lessons Learned: The Highs and Lows of Launching Multiple Startups

Lessons Learned: The Highs and Lows of Launching Multiple Startups
Entrepreneurship Startup Advice Business Growth 11 min read 4 comments

Discover the highs and lows of launching multiple startups with Ian Wiedenman, uncovering valuable lessons and insights from his journey as a serial entrepreneur.


My Journey Begins: The Spark that Ignited Somiibo

Alright, so let’s rewind a bit and set the stage. Picture young Ian, brimming with ideas and an insatiable curiosity about the digital world. It was a crisp morning, the kind where the air feels charged with potential—or maybe it was just too much coffee. Either way, I was itching to create something. That’s when the light bulb moment happened: Somiibo.

Now, you might be wondering, “What in the world is Somiibo?” Great question! Somiibo started as an ambitious idea to help people automate their social media tasks. I mean, who doesn’t want a little more free time, right? The concept was simple, yet packed with potential—an app that could handle the mundane, repetitive tasks of social media management, allowing users to focus on what really matters: creating amazing content and engaging with their audience.

But let’s not sugarcoat it—getting Somiibo off the ground was no walk in the park. The initial days were a whirlwind of coding marathons, caffeine-fueled brainstorming sessions, and, of course, the occasional existential crisis. There were moments when it felt like I was trying to juggle flaming swords while riding a unicycle. But hey, what’s a startup journey without a little chaos?

One of the biggest challenges was figuring out the balance between functionality and user-friendliness. I wanted Somiibo to be powerful, but not at the expense of simplicity. It’s like trying to create a gourmet meal that’s still easy enough for a college student to whip up—no pressure, right? But with each line of code, each test run, the vision started to take shape. Somiibo was becoming real, and that was a thrill like no other.

As the app began to attract its first users, the feedback poured in. Some of it was glowing, some… not so much. But every piece of feedback was a nugget of gold, guiding me on how to tweak, improve, and pivot. It was a steep learning curve, but every stumble was a step forward.

Looking back, those early days were a mix of triumphs and tribulations. There were high fives for every feature that worked seamlessly and sighs of frustration for every bug that refused to be squashed. But through it all, the spark that ignited Somiibo kept burning bright, fueled by a passion to create something truly valuable.

So, there you have it—the beginning of my journey with Somiibo. It was a wild ride, filled with lessons, laughter, and a fair share of late-night coding binges. And little did I know, this was just the start of an epic adventure in the world of startups. Stay tuned, because the story only gets more interesting from here.

Early Triumphs and Tribulations: Building the Foundation

Ah, the early days of launching startups. There’s nothing quite like the rollercoaster ride of emotions, the sleepless nights, and the caffeine-fueled brainstorming sessions. When I first set out to create Somiibo, I had a head full of dreams and a heart full of determination. Little did I know, I was about to embark on a journey that would teach me more than any business school could.

In the beginning, success came in small, thrilling doses. Imagine hitting your first 100 users and feeling like you’ve just won the entrepreneurial lottery. Each milestone, no matter how tiny, felt monumental. I remember the sheer joy of our first positive feedback – a simple “This is awesome!” comment on a social media post. It was like a pat on the back from the universe, saying, “Keep going, you’re onto something!”

But, as with any great story, there were plot twists. Building the foundation of Somiibo was not without its trials and tribulations. For every triumph, there seemed to be a corresponding setback. Just when I thought I had the perfect marketing strategy, a competitor would pop up with a shinier toy, leaving me scrambling to innovate yet again.

One of the biggest challenges was balancing the act of being a visionary and a realist. On one hand, I had grand ideas that could revolutionize the space we were in. On the other, I had to keep my feet on the ground and ensure that we were building something sustainable. This often meant making tough decisions, like cutting features that I loved but that didn’t quite fit the immediate needs of our users.

Then there were the technical hiccups. Oh boy, the technical hiccups. From server crashes to unexpected bugs, it sometimes felt like our code had a mind of its own – and not a very cooperative one at that. Each glitch was a mini-crisis, but also a learning opportunity. I quickly learned the importance of having a solid troubleshooting process and a resilient team that could roll with the punches.

Speaking of team, finding the right people was another adventure. In the startup world, your team is your family. You laugh together, you cry together, and sometimes, you even argue like siblings. Building a cohesive team that shared my vision and could execute it skillfully was crucial. I realized that hiring isn’t just about skills on paper; it’s about finding people who are as passionate and committed as you are.

Amidst the chaos, I also discovered the power of community. Engaging with other entrepreneurs, attending networking events, and seeking advice from those who had walked the path before me proved invaluable. Their stories of success and failure gave me perspective and often, much-needed encouragement.

Looking back, those early days of building the foundation for Somiibo were a mix of euphoria and exasperation. But every high and low was a stepping stone, leading me to where I am today. The key takeaway? Embrace the journey, learn from every experience, and never lose sight of your vision.

For those of you on a similar path, remember that the foundation you lay today will support the skyscrapers of tomorrow. And trust me, the view from the top is worth every bit of the struggle.

Expanding the Vision: From Somiibo to Slapform.com and Beyond

So, there I was, riding high on the initial success of Somiibo, feeling like I could conquer the world. I mean, who wouldn’t feel invincible after launching a project that actually took off? But as any veteran entrepreneur will tell you, the real challenge isn’t the first win; it’s what you do next. For me, that meant expanding my vision and diving headfirst into new ventures.

If you’ve been following my entrepreneurial journey, you know I’m not one to rest on my laurels. After Somiibo, I was itching for the next big thing. Enter Slapform.com. This project was born out of a simple idea: streamline the creation of online forms. Sounds mundane, right? But trust me, the devil is in the details, and there’s a lot more to forms than meets the eye.

The journey from Somiibo to Slapform.com was anything but linear. There were days when I questioned my sanity—like, why did I think I could juggle multiple projects without losing my mind? Oh, the hubris! But there were also moments of sheer joy and enlightenment, the kind that make you feel like a mad scientist who just discovered the elixir of life. The key to managing this chaos? Balancing creativity with practicality, a lesson I delve deeper into here.

Expanding my vision also meant embracing new challenges and opportunities. Somiibo was a fantastic starting point, but I wanted to push the envelope further. That’s how projects like StudyMonkey.ai came into play. If you’re curious about the evolution from Somiibo to StudyMonkey, check out this post. It’s a wild ride, trust me.

Each new venture brought its own set of highs and lows. There were times when I felt like I was juggling flaming torches while riding a unicycle—one wrong move, and everything could come crashing down. But those are the moments that teach you the most. I learned to adapt, pivot, and sometimes even completely overhaul my approach. It was a continuous process of iteration, not just with the projects but with myself as an entrepreneur. For a deeper dive into adaptability, you might find this article helpful.

One of the biggest lessons I learned through this expansion phase was the importance of prioritizing what truly matters. It’s easy to get caught up in the excitement of launching something new, but without a clear focus, even the best ideas can fizzle out. For me, it’s all about finding that sweet spot where passion meets practicality. Curious about how I manage to juggle multiple projects without losing my sanity? I’ve shared some of my strategies here.

As I continue to expand my vision and take on new challenges, I’m constantly reminded of why I embarked on this journey in the first place. It’s not just about the end goal but the exhilarating process of getting there. And let’s be honest, the occasional mishap or unexpected twist only adds to the adventure.

So, what’s next on the horizon? Well, if history is any indication, it’s bound to be another rollercoaster ride of innovation, adaptation, and perhaps a few sleepless nights. But hey, that’s the life of an entrepreneur, right? And I wouldn’t have it any other way. For more insights into my ongoing journey, you can always check out my personal blog here.

Lessons Learned: What Worked, What Didn’t, and Moving Forward

Reflecting on my entrepreneurial journey from Somiibo to Slapform.com and beyond, it’s like riding a rollercoaster—full of exhilarating highs and stomach-churning lows. So, what pearls of wisdom have I gathered along the way? Let’s dive into the nitty-gritty of what worked, what didn’t, and how I’m moving forward.

First off, let’s chat about the wins—those shining moments that keep you going when things get tough. One thing that certainly worked was embracing the concept of constant reinvention. Now, I know what you’re thinking: “Isn’t that exhausting?” Well, yes, but also incredibly rewarding. Staying adaptable and fresh is crucial. Each pivot and tweak, though sometimes painful, often brought me closer to a more refined and successful version of my startups. For more on my beliefs about reinvention, check out this post.

But let’s not sugarcoat it—mistakes were made. Oh boy, were they made. One major pitfall was underestimating the importance of market research. I can’t count the number of times I thought, “This idea is brilliant! Everyone will love it!” only to find out later that “everyone” was more like “a handful of people, and maybe my mom.” Thorough market research helps avoid these missteps and ensures you’re addressing real needs rather than imagined ones.

Another lesson learned the hard way was the significance of a solid support system. Being a solopreneur can sometimes feel like you’re stranded on an island. Sure, you have the freedom to make decisions, but you also bear the weight of those decisions. Building a network of mentors, advisors, and like-minded entrepreneurs can provide invaluable insights and moral support. Trust me, it’s easier to navigate the choppy waters of startup life when you’re not paddling alone.

Now, let’s talk about moving forward. One strategy that has been a game-changer for me is the art of scaling up. As my projects grew, so did the complexity of managing them. Adopting scalable solutions and smart delegation became crucial. Curious about scaling strategies? I’ve got a detailed guide here.

In addition, keeping the creative juices flowing is essential. Innovation isn’t a one-time event; it’s a continuous process. Whether it’s brainstorming with a random doodle on a napkin or having a full-fledged ideation session, staying creative keeps the momentum going. For a peek into my creative process, you can read more here.

As I move forward, I remain committed to learning and evolving. The startup landscape is ever-changing, and staying stagnant is not an option. Whether it’s launching a new project or refining an existing one, the journey of a solopreneur is an ongoing adventure. Want to know what keeps me motivated? Dive into my thoughts here.

In conclusion, launching multiple startups has been a wild ride filled with lessons on what works and what doesn’t. By embracing reinvention, conducting thorough market research, building a support system, scaling smartly, and fostering creativity, I continue to navigate this thrilling journey. And remember, each stumble is just a stepping stone to success.

About

Follow my journey as a solopreneur, and my evolution from launching Somiibo, a single project, to expanding my empire with multiple innovative projects like Slapform.com, StudyMonkey.ai, and more