Question 1

What is Don-Bot?

Accepted Answer

Don-Bot is a simple way to ask me the questions people would normally ask a candidate, without turning it into a campaign event. You pick a question, and you get my answer. No email capture. No donation pitch. No clipboard.

Question 2

Are these answers really from Don?

Accepted Answer

Yes. These answers are based on my views, my experience, and how I think about Bedford. AI helps organize and present them, but it does not invent my positions. If I put my name on something, I should be able to stand behind it.

Question 3

Why can't I type my own question?

Accepted Answer

Mostly because I wanted this to be useful, not chaotic. Most people ask some version of the same core questions. So this starts with the questions Bedford residents are most likely to care about. If enough people ask about something missing, we can add it.

Question 4

Is this supposed to replace talking to you?

Accepted Answer

No. It is supposed to make basic answers easier to find. A website can answer common questions. It cannot replace judgment, conversation, or accountability.

Question 5

Why are you running for Town Supervisor?

Accepted Answer

Because Bedford deserves a choice. Local government works better when people have to explain their decisions, defend their priorities, and ask for support. Uncontested elections make everyone a little too comfortable.

Question 6

Are you actually trying to win?

Accepted Answer

Yes. I am not doing this for theater. I also understand the math. Bedford is a heavily Democratic town, I am a Republican, and national politics makes that harder. But local elections should still be about local judgment, local service, and whether residents want another choice.

Question 7

What does success look like even if you do not win?

Accepted Answer

Success means Bedford had a real election. It means more people understood what the Town Supervisor does. It means residents had clear answers on local issues. And it means we showed that a campaign can be useful, transparent, and serious without spending a fortune.

Question 8

What is the basic argument for this campaign?

Accepted Answer

You do not have to vote for me to believe Bedford should have a choice. That is the starting point.

Question 9

Who are you?

Accepted Answer

I am a Bedford resident with deep roots here. I first moved to Bedford Village in fourth grade. After graduating from Vanderbilt, I returned to Katonah to raise my family and build a business. Bedford is not a campaign backdrop for me. It is home.

Question 10

Have you held office before?

Accepted Answer

Yes. I served five years on the Bedford Town Board. I have also served as president of the Katonah-Lewisboro School Board and as a Katonah Fire Commissioner. So I am not new to local government, local budgets, or the practical work of serving this community.

Question 11

What other community roles have you had?

Accepted Answer

I have served in a number of local roles over the years: Bedford Town Councilman, Katonah Fire Commissioner, Wetlands Commissioner, vice chair of the Communications Committee, chair of the Traffic Safety Working Group, president of the Katonah-Lewisboro School Board, officer of KVIS, and member of several town and community committees.

Question 12

What did you accomplish when you served on the Town Board?

Accepted Answer

I am proud of helping hold the line on taxes while maintaining Bedford's AAA bond rating, increasing investment in roads and town assets, fighting to get I-684 paved, helping stop the sale of vaping products in our hamlets, and reducing fees paid by community groups for town services.

Question 13

What is your professional background?

Accepted Answer

I have a Bachelor of Arts degree in economics and business administration from Vanderbilt University. Professionally, I run my own legal marketing firm based in Katonah. That background matters because local government needs both fiscal discipline and clear communication.

Question 14

Why should anyone trust you with this role?

Accepted Answer

Trust is earned. I can point to prior service, community involvement, and a record of showing up. But more than that, I hope people judge the way I approach things: calmly, practically, and without pretending every issue has an easy answer.

Question 15

Why are you calling this The UNCAMPAIGN?

Accepted Answer

Because I am not running a normal campaign, and I am not going to pretend I am. No consultant choreography. No endless fundraising emails. No mailers stuffed in your mailbox. No robocalls. No fake urgency. Just a choice, some clear answers, and a campaign that respects people's time.

Question 16

Why are you refusing to fundraise?

Accepted Answer

Because I think local politics has become too dependent on money. If giving residents a choice requires a big campaign budget, that says something unhealthy about the system. I would rather show what can be done with almost nothing.

Question 17

How much are you spending?

Accepted Answer

The goal is to stay at $49.99 or less. That is deliberate. The point is not that every campaign should cost exactly that. The point is that local civic participation should not require a budget that looks like a startup seed round.

Question 18

Why no door knocking, mailers, or signs?

Accepted Answer

Because most people do not want to be bothered. If someone wants to hear from me, I am here. If they do not, I am not showing up at dinner time with a clipboard. I would rather be available than intrusive.

Question 19

Is this a stunt?

Accepted Answer

If it were a stunt, it would probably be louder. This is restrained on purpose. The point is to prove that a serious local campaign can be transparent, low-cost, technologically modern, and respectful.

Question 20

Why are you using AI?

Accepted Answer

Because it helps a small campaign do useful things without hiring staff or consultants. I would rather be honest about that than pretend otherwise. AI is a tool. The judgment still has to be human.

Question 21

What does the Town Supervisor actually do?

Accepted Answer

The Town Supervisor is the town's chief executive and chief fiscal officer. The role helps shape budgets, sets priorities, works with the Town Board, oversees town administration, and serves as a public face for how the town operates.

Question 22

Can the Supervisor do whatever they want?

Accepted Answer

No. The Supervisor works with the Town Board, town staff, state law, public process, and practical reality. It is an important role, but it is not a monarchy.

Question 23

What would your first 90 days look like?

Accepted Answer

I would start with a serious review of what is already in motion: budgets, active projects, road and infrastructure priorities, consultant relationships, staffing needs, and resident complaints. Before promising a giant list of fixes, I want to know exactly where things stand.

Question 24

How would you communicate with residents?

Accepted Answer

Regularly and plainly. Not just official documents. Not just meeting clips. Residents should be able to understand what is happening, why it matters, who is responsible, and what comes next.

Question 25

What are Bedford's biggest issues right now?

Accepted Answer

There is no single issue. There are many. Roads and infrastructure. Taxes and spending. Hamlet vitality. Overdevelopment. Affordability. Cell service. Emergency preparedness. The bigger issue is whether Town Hall has enough urgency, focus, and curiosity to deal with them.

Question 26

What did you say in the 2023 candidate roundtable that still applies?

Accepted Answer

I said then that Bedford needed a more cohesive, balanced board with energy, focus, and a plan to preserve what makes Bedford, Bedford. I still believe that. I also said the board needed to ask more questions, set clearer goals, and stop drifting without a destination. That still applies too.

Question 27

What are your top local priorities?

Accepted Answer

First, restore focus and discipline to Town Hall. Second, address roads, infrastructure, and state-road advocacy with more urgency. Third, protect Bedford's character from overdevelopment. Fourth, improve communication and transparency. Fifth, make sure spending is tied to real outcomes residents can see.

Question 28

What is Bedford getting right?

Accepted Answer

Bedford still has an extraordinary sense of place. The hamlets are distinct. The community traditions are strong. The landscape, history, and local institutions matter. This is not a tear-it-down campaign. It is a do-better-with-what-we-have campaign.

Question 29

What does Bedford need more of from local government?

Accepted Answer

Clearer goals. Better follow-through. Less outsourcing of judgment. More willingness to ask basic questions in public. A Town Board meeting should feel more like a working session and less like a series of pre-decided presentations.

Question 30

What is your view on Bedford's roads?

Accepted Answer

Residents should not feel like driving through town is a test of their suspension. Roads are basic government work. They are not glamorous, but they matter every day.

Question 31

What about the state roads?

Accepted Answer

Some of the state roads running through Bedford are deplorable and filled with potholes. The Town Supervisor may not directly control those repairs, but that cannot be the end of the conversation. The Supervisor should be actively and repeatedly pressing the people who do control them. Quiet acceptance has not worked.

Question 32

What should the Supervisor do about roads they do not control?

Accepted Answer

Be persistent. Call. Write. Meet. Escalate. Coordinate with state and county officials. Publish what has been requested and when. Residents deserve to know whether their local government is actually pushing or just explaining why nothing can be done.

Question 33

How would you handle infrastructure priorities?

Accepted Answer

Start by making them visible. What roads are town roads, county roads, and state roads? What condition are they in? What is scheduled? What is delayed? What is funded? What needs outside pressure? Competence starts with clarity.

Question 34

What else counts as infrastructure?

Accepted Answer

Roads, drainage, sidewalks, lighting, cell service, emergency systems, public buildings, water issues, and the basic assets residents depend on. Infrastructure is not just ribbon cuttings. It is whether the town works.

Question 35

Are you a NIMBY?

Accepted Answer

Yes. I am not going to dress it up. I moved to Bedford for a reason. People live here for a reason. Wanting to protect the look, feel, charm, and character of Bedford is not something I feel the need to apologize for.

Question 36

Does that mean you oppose all development?

Accepted Answer

No. It means I oppose development that is wrong for Bedford. Scale matters. Design matters. Traffic matters. Infrastructure matters. Hamlet character matters. A project can check a planning box and still be a bad fit.

Question 37

What worries you about development in Bedford right now?

Accepted Answer

The recent trend is toward projects that could fundamentally change the look and feel of Bedford. Once that character is gone, it is not coming back. We should not let vague promises or planning jargon turn Bedford into something residents never asked for.

Question 38

How should Bedford handle growth?

Accepted Answer

Carefully. Bedford is not one generic place. Katonah, Bedford Hills, and Bedford Village each have a different character and different needs. Planning should reflect that, not flatten everything into the same development template.

Question 39

Are you anti-housing?

Accepted Answer

No. I am pro-honesty. Housing policy should be specific about who it helps, where it fits, what it costs, what infrastructure it requires, and what tradeoffs come with it. Calling something housing does not automatically make it smart planning.

Question 40

What is your philosophy on taxes?

Accepted Answer

Respect that it is not the town's money. Every dollar comes from residents. Government should be careful with it, explain how it is being used, and measure whether spending is actually producing value.

Question 41

What does fiscal responsibility mean to you?

Accepted Answer

It means holding the line where possible, maintaining strong financial health, protecting essential services, and avoiding unnecessary spending. During my prior service, Bedford held the line on taxes while maintaining a AAA bond rating. That kind of discipline matters.

Question 42

Where should Bedford be more careful?

Accepted Answer

Consultant spending, vague projects, unclear metrics, and anything where the public benefit is hard to explain. If something sounds impressive but no one can tell residents whether it worked, that is a problem.

Question 43

Would you cut services?

Accepted Answer

Not as an ideology. I would ask what is working, what is not, what is duplicative, what residents actually use, and what outcomes we are getting for the money.

Question 44

Is Bedford government transparent enough?

Accepted Answer

It can be better. A document being technically public is not the same as residents understanding what is happening. Transparency should mean clarity, not just compliance.

Question 45

What would you change about Town Board meetings?

Accepted Answer

I would like to see more questions, clearer goals, and more active discussion. In 2023, I said I was often disappointed by the lack of curiosity at board meetings. I still think that matters. If you do not have a destination, any road will take you there.

Question 46

What does accountability look like?

Accepted Answer

Set goals. Publish timelines. Track progress. Explain delays. Admit when something is not working. Residents do not expect perfection, but they do deserve honesty and follow-through.

Question 47

How should residents be engaged?

Accepted Answer

Consistently and early. Not after everything feels decided. Surveys, office hours, public updates, and plain-English summaries can all help. But engagement has to be real, not decorative.

Question 48

What is your view on cell service?

Accepted Answer

Better cell coverage is vital. It is not just convenience. It affects public safety and emergency response. The town should take an active role in identifying acceptable sites and working with all stakeholders.

Question 49

How should Bedford approach cell towers?

Accepted Answer

Proactively. Town land, right-of-way property, commercial areas, and less intrusive locations should all be evaluated. When I was previously on the board, we were meeting with surrounding towns to collaborate on solutions and search for locations. That kind of approach matters.

Question 50

What does emergency preparedness mean locally?

Accepted Answer

Residents should know what to do during power disruptions, severe weather, and other emergencies. The town should have clear plans, clear communication, and practical support points residents understand before something goes wrong.

Question 51

What does public safety mean beyond policing?

Accepted Answer

Safe roads, emergency response, traffic safety, cell coverage, lighting where appropriate, and making sure basic systems work. Public safety is often practical before it is dramatic.

Question 52

Are you anti-environment?

Accepted Answer

No. Bedford's land, trees, open space, and natural character are part of what makes this town special. Conservation matters.

Question 53

What bothers you about some environmental policy?

Accepted Answer

When it becomes performative. I want to know what a policy costs, what it saves, what it accomplishes, and what burdens it puts on residents. Good environmental policy should survive practical questions.

Question 54

How should Bedford approach sustainability?

Accepted Answer

With common sense and cost-benefit discipline. If something works, show the results. If something costs residents money, explain why. If something is symbolic, be honest about that too.

Question 55

Are you a Republican?

Accepted Answer

Yes. I am a registered Republican. I am not hiding that, and I am not going to insult anyone by pretending labels do not exist.

Question 56

Why should Democrats or independents consider you?

Accepted Answer

Because local government is about local things. Roads, budgets, land use, cell service, public safety, taxes, and whether Town Hall works. I have been elected before with broad support across the political spectrum, and that is the only way a Republican can win in Bedford.

Question 57

Does your party decide how you would govern?

Accepted Answer

No. The local party gives me access to the ballot. Once there, the job is to build a coalition of thoughtful Democrats, Republicans, and independents who are willing to look at the person first, not just the party label.

Question 58

What about Donald Trump?

Accepted Answer

I understand why people ask. National politics is divisive. But Bedford's Town Supervisor does not set federal immigration policy, abortion law, tariffs, or Supreme Court appointments. If voters want to use national politics as a proxy, they can. I would rather answer for Bedford.

Question 59

Are you trying to distance yourself from the Republican Party?

Accepted Answer

I am trying to be honest. I am a Republican running for local office in a very Democratic town. I believe in local government, fiscal responsibility, and practical problem-solving. I also believe Bedford works best when people are willing to think beyond party labels.

Question 60

Does partisanship belong in local government?

Accepted Answer

Less than it currently does. Local government should not be sidetracked by national partisanship. People can disagree strongly on national issues and still want potholes fixed, taxes watched, cell service improved, and overdevelopment taken seriously.

Question 61

Is this campaign just a vanity project?

Accepted Answer

No. If it were a vanity project, I would probably be spending more money and talking more about myself. This campaign is about giving Bedford a choice and proving local politics can be done differently.

Question 62

Are you qualified?

Accepted Answer

Yes. I have served five years on the Bedford Town Board, served as president of the Katonah-Lewisboro School Board, served as a Katonah Fire Commissioner, chaired the Traffic Safety Working Group, and spent many years involved in local civic organizations. Voters can decide whether that experience, judgment, and record of service are what they want.

Question 63

What is the most legitimate criticism of you?

Accepted Answer

Some people may decide that being a Republican in Bedford is enough to vote against me. Others may think this campaign is too unconventional. I understand both reactions. My answer is to be direct, answer questions, and let people judge the substance.

Question 64

Would you criticize the current administration?

Accepted Answer

Where criticism is warranted, yes. But I am not running a campaign built around personal attacks. If something has been done well, I can say that. If something has been neglected, I can say that too.

Ask Don. Without the clipboard.

Ask a Question

Pick a question.

How This Was Built

Step 1 — Campaign context

Step 2 — Build prompt

Step 3 — Q&A authoring

Step 4 — Upgrades

Why document this?