May 13, 2026

Interview Series: Michael Ding on Estimating Work and Software Improvements

43 minutes

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Episode #164

Meet Michael Ding, the brilliant young man behind the revolutionary BobYard bidding software! In this episode, Marty is joined by BobYard founder and CEO Michael Ding to discuss the inspiration behind their takeoff software and how it saves time for estimators and salespeople. They talk about the journey to create the tool, how systems can make estimates more consistent, and what teams can do to spend more time on the activities that actually drive value for companies.

BOBYARD is an AI-powered takeoff and estimating platform that automates the most time-consuming parts of bidding work. Contractors report up to 65% reduction in takeoff time and 3-5x more bids submitted per estimator.

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Key Learnings

The Best Businesses Solve Hard Problems with No Shortcuts: If a market has a shortcut, everyone takes it and you end up competing on price. Pick problems where the only solution is the hard one. Then nobody can follow you without doing the hard work too.

Estimators Should Sell, Not Click: Before BobYard, 50 percent of an estimator's day was spent clicking on screens doing takeoffs. Estimators are some of your most savvy people. Their job is to bring in money, not to count plants.

An Order of Magnitude Better Changes the Conversation: A 10 percent improvement is a hard sell. A 10x or 100x improvement sells itself. BobYard cuts a 4-5 hour commercial takeoff down to 30-60 minutes. That is not marginal, that is transformational.

Hire People Better Than the Average: Every new hire should be better than the previous one. It forces the existing team to grow into a new bar. The best hires shatter your expectations of what a great hire looks like.

Ownership Means Other People Sleep Well: Define ownership by how easy everyone else can sleep at night knowing you are in charge of your area. If you are losing sleep over something, that is a sign someone needs clearer ownership of it.

Trust and Ownership Are Two Sides of the Same Coin: If you do not trust someone, you will not give them ownership. If you do not give them ownership, they know you do not trust them. Great people want autonomy and partnership.

Do Not Go Looking for Nails with a Hammer: Do not ask “where can we apply AI in our business?” Ask “where can we improve?” Then pick the right tool. Sometimes it is AI. Sometimes it is just better systems or a clearer SOP.

Run a Real AB Test on Software Vendors: The best customers ab test products, run paid trials, build financial models for the ROI. Smaller companies often buy on emotion. The exercise of evaluating software forces you to actually understand your own business.

Self-Reflection Is the Hardest Leadership Skill: It is hard to have people tell you the truth when they report to you. The best leaders build enough trust that their team will tell them when they are wrong.

Reflection Questions

How much of your estimator's day is spent on actual selling versus clicking through takeoffs? What would it look like if that ratio flipped?

Where in your business are you taking the easy path because it is what everyone else does? What hard problem could you take on instead?

Who on your team has clear ownership of their area, and who is waiting on you to make every decision?

Resources:

BOBYARD

Aspire

ACE Peer Groups

Virtual Sales Bootcamp

Grunder Landscaping Field Trips

The Grow Group

Grunder Landscaping

Marty Grunder LinkedIn