In the ever-evolving world of technology, launching a startup has always been a daring, exhilarating pursuit. But the path to building Sundog in 1996 versus Teiken Gramer & Co. 2025 couldn’t be more different. Each era brings its own set of opportunities, barriers, and expectations. In reflecting on the experience, what a difference 30 years makes. Here’s a look at how the startup game has changed and what that means for today’s founders.
The Cost of Entry
1996:
Starting a tech company was expensive. You needed physical servers, office space, and typically on-premise software (and of course an ISDN line). Sundog grew as a result of building high-end, complex websites that few had the experience to build; today – it just requires a simple web editor. Hardware and infrastructure were capital-intensive, which meant most startups needed early-stage funding or personal capital just to get off the ground.
2025:
Cloud computing, open-source software, and low-code/no-code tools have slashed startup costs. You can launch a global product with a laptop and a Wi-Fi connection. Platforms like AWS, Stripe, and GitHub make it possible to scale without a large upfront investment.
Access to Funding
1996:
Venture capital was concentrated in a few tech hubs like Silicon Valley and Route 128 in Boston. Angel investors were rare, and if they did invest, most had no idea what they were investing in – they just wanted anything with a “.com”. Accelerators like Y Combinator didn’t exist yet. Most startups relied on banks, bootstrapping, or strategic partnerships. I can still remember how good it felt to secure a $50,000 SBA loan in 1996 and the impact that loan had on Sundog’s growth.
2025:
There’s a global ecosystem of VCs, angels, syndicates, crowdfunding, and revenue-based financing. Startups can raise capital from anywhere in the world. But with greater access comes greater competition and higher investor expectations.
Talent and Teams
1996:
Finding technical talent was a huge bottleneck. Software engineers were in high demand but scarce and we were competing with Great Plains Software>Microsoft. Most teams were local, and collaboration tools were limited to email and phone calls.
2025:
Remote-first companies are the norm. Founders can hire global teams using platforms like Deel or Remote. AI-powered tools accelerate product development, and platforms like GitHub Copilot help engineers write code faster than ever.
Market Readiness and User Behavior
1996:
The internet was still a novelty. Many consumers and businesses were just coming online. I still recall the board room debates with company executives telling them where their customers would be in 5 years. Convincing users to adopt digital solutions was often an uphill battle. Scaling was slower because internet penetration and digital fluency were low.
2025:
Digital is default. From smartphones to smart homes, users are comfortable with tech in every part of their lives. You can reach millions instantly through app stores, social media, and digital marketing.
Competition and Differentiation
1996:
Fewer startups meant less competition, but it also meant fewer playbooks, less mentorship, and slower market feedback. First-mover advantage was real, and many problems were being solved for the first time.
2025:
The barrier to entry is lower, but the barrier to success is higher. Every idea has 10 clones. AI-generated products flood the market. Brand, execution, and user experience are more critical than ever.
Regulatory and Ethical Complexity
1996:
Startups operated with relative freedom. Regulations around data, privacy, and platform accountability were minimal. That freedom came with risk but also agility.
2025:
Founders must navigate a complex web of global data privacy laws (GDPR, CCPA), ΑΙ ethics, cybersecurity standards, and platform dependencies. It’s a more mature and heavily monitored ecosystem.
Tools, Platforms, and Ecosystem Support
1996:
Everything had to be built from scratch your own payment processor, your own data infrastructure, your own partner/customer relationship management and support tools.
2025:
Founders stand on the shoulders of giants. You can plug into ecosystems like Shopify, AWS, or OpenAI. Build fast, test fast, and scale fast.
So, Which Era Was Better?
If you’re measuring by speed to launch, access to capital, or global reach, 2025 is the golden age for entrepreneurs. But if you’re drawn to pioneering uncharted territory, owning a niche, or building before the playbooks existed, 1996 had its magic.
The truth? Both eras required boldness, creativity, and grit – just in different ways.
The Bottom Line
In 1996, you needed to build the internet. In 2025, you need stand out in it. Very different challenges. Same need for grit.
Contact
For questions on this First Principles Brief, or leadership development and program implementation, please contact:
Brent.Teiken@teikengramer.com
Phone: 701-306-5525
We’ve been through it. We’ll help you prepare for it.