Tobin Aldren

Personal profile

Tobin Aldren

Business & Technology

I’ve built several startups and had multiple exits. The contract I most regret was one I was proud to sign.

I like talking about the decisions that don’t make it into the pitch. How much say should one customer have in what we build? When should I back a new technology, and when should I get out of my team’s way?

How I got started.

I was born in the late 1980s and spent school breaks helping out at my family’s manufacturing business. When a machine stopped, I wanted to know why. Whoever had promised the customer a Thursday delivery wanted to know how much time we’d lost. These days I ask both questions.

Why a repair firm bought another monitor

After my MSc in computer engineering, a maintenance engineer and I started building monitors for production lines. Ours kept a record of what happened in the moments before a line stopped. I liked how much we could measure. The repair firm bought it because its technician could turn up with the right tools. When they asked for another monitor for another plant, I finally understood what we were selling.

I earned my MBA part-time while we ran that business. To keep growing, we needed service people close to our customers. A distributor that already had those people offered to buy the company. My partner and I could have spent years building the same network. We chose to sell.

The contract that cost us a customer

Working with distributors, I kept seeing salespeople promise dates their warehouses couldn’t meet. That gave me the idea for a software business. We built a shared order book so both teams could see which deliveries were slipping. Our customers renewed because they could call a buyer while there was still time to offer an alternative.

Then a big prospect wanted its own version. I signed the contract and put our best engineers on it. The installation ran late, and fixes we’d promised everyone else took even longer. When a long-standing customer left, I went to see the operations manager. She opened the spreadsheet her staff had gone back to using. I’d noticed they’d stopped filing support tickets. Until that visit, I thought that was good news.

I returned part of the fee and wound down the custom release. I also gave our product lead the final say on custom work, including deals I brought in myself. By the time a software group bought us, we had one product we could support and a team that could run it without me. I was proud to sell a business that didn’t need its founder in every meeting.

What I took with me after the sale

I stayed with the buyer to lead an international product team. One customer wanted its branches to pool orders without revealing what each branch paid its suppliers. We let the branches share quantities, keep their terms private and see who had opened them. I learned exactly what security was worth on that deal. If the branches couldn’t choose what to share, nobody was going to buy.

Today I’m building software that helps purchasing teams catch changes in a supplier’s revised offer. AI can flag a shorter warranty and show the buyer the passage it found. The buyer knows whether it’s worth a phone call. I ask teams to try it on one purchasing category before they commit. I still like the second order better than the first.

What I pay attention to now.

Alongside my own business, I advise founders and product teams. I kept hearing the same questions in private, so I started working through them in public. I’m especially interested in hearing from someone who tried my advice and got a different result.

The customers who leave quietly

A renewal tells me more than a compliment. So does the customer who stops asking for help. These days I want to see what they’ve gone back to doing by hand.

Who can tell the founder no?

I gave a product lead the right to turn down custom work. The first time she turned down one of my deals, I wanted to explain why this one was special. I’d hired her to save the team from exactly that argument.

What AI makes possible

I’m interested in the buyer who finally has time to read the exception before accepting a supplier’s terms. Show me what the tool found, where it came from and who gets to decide. Then we have something worth discussing.

What would change my mind

Sometimes a founder shows me a spreadsheet that costs almost nothing and works just fine. I’m in the software business. I’d still tell them to keep it.

What decision are you facing?

Follow me for short pieces on products, growth and technology. If you’re debating whether to take a big order that would pull your team off course, I’d like to hear what’s at stake. I’m just as interested in the deal you turned down.