As a bootstrapped founder, every decision you make impacts your business—especially when it comes to hiring. I've made my share of mistakes, and they were costly. In this article, I want to share what I've learned so you can avoid the same missteps, particularly when hiring through platforms like Upwork.
1. Hiring Too Quickly
Turning your idea into a working product feels incredible. That rush to start building can push you to hire the first person who seems capable. I get it—I've been there. But hiring too fast can lead to bigger problems down the line.
Tip: Slow down. Be picky. If something feels off, trust your gut and move on. The urgency you're feeling? It's probably not as critical as it seems.
Do you really need to hire for this? One of my biggest mistakes was trying to outsource strategy. They say, "Don't hire unless you're feeling the pain," and they’re right. I was so caught up juggling my day job and product development that I stopped talking to users. No freelancer can take on the responsibility of truly understanding your customers.
2. Not Firing Quickly
I used to ignore red flags. Maybe a freelancer lied about their location or got defensive about feedback. Maybe they talked a good game but couldn't deliver. I overlooked it because they were "good enough" in other areas. Big mistake.
Tip: If something's off, cut ties early. Revisit your freelancers' performance regularly—are they still bringing value? If not, it might be time to move on. It’s better to make a tough call now than regret it later.
3. Hiring Inexperienced People to Save Money
Trying to save money by hiring cheaper, less experienced freelancers? Been there. But it often ends up costing more in the long run—projects drag on, and quality suffers.
Tip: For part-time roles, look for freelancers with full-time jobs at reputable companies. They often bring solid skills and consistency without relying entirely on freelance income. The work gets done better and faster.
4. Outsourcing Core Responsibilities
I avoided talking to users because it intimidated me. I focused entirely on building the product and wrongly assumed I could outsource product strategy and user engagement. I even relied on a freelancer’s vision and domain knowledge, hoping that just following her direction would lead to the right product. I was wrong. This disconnect led to poor decisions and a product that didn’t resonate. No freelancer can own the vision the way a founder must.
Tip: As a bootstrapped founder, you can't avoid tough tasks like user research and strategy. You need to own these responsibilities. Freelancers can help execute, but they can't define your product's direction.
5. Vague Communication and Expectations
I once assumed a freelancer "got" what I wanted without explaining things clearly. Unsurprisingly, the results didn’t match my expectations.
Tip: Spell everything out. Provide detailed briefs, schedule regular check-ins, and set clear milestones. Good communication upfront prevents headaches later.
Smarter Hiring on Upwork
Upwork is an amazing place to find talent, but you need a plan. Here's what works for me:
1. Skip Freelancers with $0 Earnings If they haven't completed any jobs, it's hard to gauge their reliability. I stick with freelancers who have a track record.
2. Avoid Agencies Agencies can be pricier due to added overhead, like case managers, and you often don't know upfront who will actually be working on your project. During interviews, I make sure to confirm that the freelancer I'm speaking with will be the one personally handling the work. Direct communication keeps expectations clear and accountability strong.
3. Start Small Before committing to a big project, assign a small paid task. It’s the best way to test their skills and work ethic.
4. Check Their History Dig into their past projects and client reviews. Consistency in quality and meeting deadlines is a good sign.
5. Set Clear Expectations Be upfront about goals, deliverables, and deadlines. Clear expectations make for smoother projects.
Hiring as a bootstrapped founder isn't easy, and mistakes can be expensive. But by learning from my experiences and using platforms like Upwork strategically, you can avoid costly errors. Take your time, trust your instincts, and build a team that truly supports your business's growth.