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Lessons from the Trenches: Startup Tips from a 5-Time Founder in Logistics Tech

Starting a company is hard. Starting a logistics and supply chain company—where tech expectations are high and margins are tight—is even harder. After five startups in this industry, I’ve learned a few lessons that may help others just starting their journey. Here are some tips I’d offer to any logistics tech founder trying to build something from […]

Starting a company is hard. Starting a logistics and supply chain company—where tech expectations are high and margins are tight—is even harder. After five startups in this industry, I’ve learned a few lessons that may help others just starting their journey. Here are some tips I’d offer to any logistics tech founder trying to build something from the ground up:

1. Use Fractional Roles and Gig Services Early

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Full-time hires are expensive—and often unnecessary in the early stages. Many highly experienced professionals are open to fractional roles in startups, often at a discount to market rates in exchange for equity and upside potential. This is one of the most efficient ways to bring executive-level talent into a lean team.

Sure, you can do a lot yourself—especially with a good AI helping—but your time will already be stretched far beyond capacity. Don’t overlook gig services like Freelancer, Upwork, or Fiverr for one-off tasks like formatting pitch decks, designing marketing one-pagers, or creating simple explainer videos. It’s a time vs. cost decision, and handing off smaller tasks is one of the best ways to stay focused on what really moves the business forward.

 

2. Don’t Launch Without a CFO

One role that deserves its own category is CFO. In my opinion, it’s nearly impossible to launch a serious company, especially one that plans to raise money, without a CFO. Fundraising, equity structuring, cap table modeling, forecasting, and investor communication are not optional. A CFO will pay for themselves often, even before your first term sheet arrives. While you may not need someone full-time, this is a great candidate for a fractional role—someone who’s been through raises and knows how to speak investor language. It will save you from making expensive mistakes.

JP Wiggins

3. Surround Yourself with Mentors—But Filter the Advice

Mentors are invaluable. You’ll need a few people who’ve been through the grind and can spot issues before you do. But know this: not all advice fits your company or era. For example, AI is reshaping how we build and scale logistics platforms. If your mentor’s experience predates this wave, their advice may not align with the modern toolkit. Take the advice, weigh it, and remember—your job is to choose what fits your context.

4. Startup Pricing Is Everywhere—Ask for It Every Time

Everything you buy from CRMs to payroll to booth space at trade shows probably has startup pricing. Ask. Again and again. We’ve received 80% off our CRM, free HubSpot onboarding, massive savings on AWS and Azure, and even discounted trade show sponsorships—all because we asked. Your investors might also have portfolio discounts they can unlock, especially if they’re plugged into accelerators or venture networks. Don’t leave that money on the table.

5. Tools Multiply—Simplify Early or Drown Later

Startups accumulate tools like socks in a teenager’s room. You’ll sign up for a CRM, payroll service, website hosting, document management, customer support portal, email service, office suite, etc. Each is important, but each adds a management burden. Assign someone (even if it’s you) to own the tech stack early and keep it lean. Redundancy and overbuying sneak in faster than you think.

6. Fundraising is About More Than Money

Not all money is created equal. The right investors do more than fund you—they open doors, make introductions, offer operational insights, and help build your company strategically. The wrong investors? They can sink you.

Fundraising takes more time—and more effort—than most founders expect. Pitching VCs today isn’t like it was three years ago. Money is tight, and investors are extremely selective. Plan on giving 100 pitches, then plan on doing it 100 more. Learn from the “no’s”: ask why they passed, and more importantly, ask who else they know that might be a better fit.

When raising, don’t just focus on check size. Ask what else they bring to the table. Will they introduce you to customers? Will they help you build a board? Do they understand your space? Some investors specialize in pre-seed or seed rounds; others only engage at Series A or later. Build your network early, and always plan ahead for your next fundraise.

7. Hire Smart Over Experienced

When you’re building a startup, especially one doing something new or disruptive, experience isn’t always the best predictor of success. Smart people adapt, figure things out, and thrive in the ambiguity that defines startup life. Some of our best hires didn’t have deep logistics experience, but they had the horsepower to learn fast and contribute meaningfully. Experience helps, but grit, curiosity, and brainpower win.

8. Understand the Incubator Trade-Off

I never joined an incubator—I didn’t want to give up 10% of my company that early. But I see the appeal. The right incubator brings mentorship, pitch feedback, investor exposure, and early tech discounts. That environment can be catalytic if you’re a solo founder or first-timer. Just know what you’re trading and make sure the value you get matches the equity you give.

9. Be Blunt and Clear in Your Messaging

No one has time to decode buzzwords. You need a clear elevator pitch. It has to be simple—which is especially hard in logistics—but it has to be simple. If your pitch requires a diagram to explain, you’ve already lost your audience. Focus on clarity over cleverness. As much as possible, use real names and real case studies. Say: “Jarrett Logistics used us to connect 30 carriers in 30 days—no developers needed.” That’s what people remember. Real outcomes speak louder than polished taglines.

10. Overdeliver—It’s Underrated

Overdelivering is one of the most underrated strategies in startups. Your first few customers define your company—how it works, how it’s perceived, and how far it can go. If they fail, you will fail. These aren’t just customers; they’re references, co-creators, and possibly even future investors. Invest your time and energy into making them successful; they’ll help carry you forward.

JP Wiggins is a five-time startup founder in logistics tech and the CEO of 1 Logtech Inc., a no-code iPaaS platform that simplifies integrations across shippers, 3PLs, and carriers. He previously co-founded 3GTMS (acquired by Descartes), G-Log (acquired by Oracle), WSDC (acquired by RedPrairie), and DX/DT (acquired by Descartes) and has spent decades building, scaling, and advising startups across the transportation and supply chain industry.

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