What Does Success Look Like to You? — Blake Osgood

What Does Success Look Like to You? — Blake Osgood

How do you define your role today beyond your formal title?

I think of myself as a problem-solver more than anything else. I own Ozgood Land Restoration, where I work with landowners to restore property overtaken by invasive plants or that needs to be returned to healthier pasture or habitat. I have also started Osgood Equity Recovery, which involves identifying potential unclaimed funds connected to property tax sales and helping eligible people pursue the recovery process. The businesses are very different, but my role in both starts with looking closely at a situation, understanding the problem, and figuring out whether there is a practical way I can help.

What decisions occupy most of your attention right now?

A lot of my attention is going toward balancing an established business with something new. Ozgood Land Restoration has given me a clear understanding of the kind of work we do and the landowners we serve. Osgood Equity Recovery is newer, so I am spending more time learning, researching, and refining the process. I do not want to grow something simply for the sake of growth. I want to understand where I can genuinely provide value before deciding how far to take it.

What connects land restoration and equity recovery for you?

The connection is seeing potential that is easy to overlook. With land restoration, I can walk onto an overgrown property and see healthy pasture underneath years of invasive growth. With equity recovery, I may find records suggesting that funds remain from a tax sale that someone may not realize could be available to them. In both situations, the first impression does not tell the whole story. You have to look closer and do the work required to understand what is actually there.

How has your approach to solving problems changed throughout your career?

I ask more questions now. Earlier in my career, I probably put more value on having an answer quickly. Experience has taught me that speed does not help much if you are solving the wrong problem. My background in project management taught me to gather information, understand the moving parts, and think about what could happen next. I still use that approach whether I am evaluating a piece of land or researching a potential equity recovery.

How do you decide where to spend your personal time and energy?

I use a whiteboard with five time horizons: one week, one month, six months, one year, and five years. It gives me a way to separate what needs my attention today from what I am trying to build over several years. I have been self-employed since 2013, and one thing I have learned is that there will always be something demanding your attention. If you only respond to whatever feels urgent, it is easy to lose sight of where you are actually trying to go.

What has starting Osgood Equity Recovery taught you about entering a new field?

It has reminded me how much you do not know when you first start looking at a problem. I became interested after learning that excess proceeds can sometimes remain following property tax sales and that people may not always realize those funds exist. From there, I had to understand how the process works, what varies between jurisdictions, and what information is needed before determining whether someone may have a valid claim. It has reinforced my belief that curiosity is useful, but you have to follow curiosity with research.

How do you approach trust when contacting someone about potential unclaimed funds?

I understand why someone would be skeptical. If somebody I did not know called me and said there might be money connected to a property I previously owned, I would ask questions too. My job is to explain why I am contacting them, what I found, how the process works, and how I am compensated. Osgood Equity Recovery operates on a contingency basis, so my fee is tied to a successful recovery. I do not think trust comes from telling someone to trust you. It comes from being clear enough that they can evaluate the situation for themselves.

What assumptions about business do you regularly challenge?

One assumption I question is that you need to stay in the same industry for your entire career for your experience to be useful. I have worked in project management, spent years as a defense contractor, run my own businesses, ranch cattle and other livestock, built a land restoration company, and now work in equity recovery. Those things may look disconnected on paper, but I use many of the same skills in all of them. Research, planning, communication, judgment, and follow-through transfer surprisingly well.

How do you know when an opportunity is worth pursuing?

I start by asking whether there is a real problem. Then I ask whether I can actually contribute to solving it. Those are two different questions. Something can be interesting without being a good business opportunity. I also consider what could go wrong, what I do not understand yet, and whether the outcome creates real value for the person I am serving. If I cannot answer those questions comfortably, I probably need to keep researching.

How do you balance confidence with uncertainty when making decisions?

I try to be confident about what I know without pretending to know what I do not. Land restoration taught me that lesson repeatedly. I have gone onto properties expecting one thing and changed my plan after walking the ground. Equity recovery has similar uncertainty because finding potential funds does not automatically mean a successful recovery will happen. Facts can change the direction of the work. I would rather adjust when I learn something new than stay committed to a decision simply because it was my original plan.

What has self-employment taught you about responsibility?

There is nobody else waiting to make the difficult decision for you. You have to decide where to spend money, where to spend time, which opportunities to pursue, and which ones to walk away from. You are also accountable to the people who trust you. In land restoration, someone may be trusting me with property their family has owned for generations. In equity recovery, someone may be trusting me to help navigate a process involving money they may be entitled to pursue. I take both responsibilities seriously.

How do you measure progress when results are not immediate?

I look for evidence that the process is moving in the right direction. With land, that might mean native grasses returning, invasive species becoming less dominant, or wildlife using the property differently. With equity recovery, progress is more procedural. It can mean verifying records, locating the appropriate person, establishing whether a potential claim is worth pursuing, and moving through the required steps. I have learned not to confuse activity with progress. I want to know that each step is getting us closer to a meaningful outcome.

What kind of impact do you hope your businesses have over time?

I want to build businesses that solve understandable problems and produce outcomes people can actually recognize. With Ozgood Land Restoration, that means leaving land healthier and more useful than it was when we arrived. With Osgood Equity Recovery, it means helping people investigate and, when possible, recover funds they may not have known were available to them. I do not know exactly what my businesses will look like ten years from now, but I know I want to keep doing work where I can point to the problem and understand why solving it matters.